# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Yue Wang' _publ_contact_author_email YUEWANG@JLU.EDU.CN _publ_section_title ; Polymorphs and Luminescent Properties of a Cetyl Substituted Quinacridone Derivative ; loop_ _publ_author_name 'Yue Wang' 'Yan Fan' 'Weifeng Song' 'Kaiqi Ye' 'Dingyi Yu' 'Jingying Zhang' # Attachment 'Revised-CIF_for_a_and_b.CIF' data_a _database_code_depnum_ccdc_archive 'CCDC 700174' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H76 N2 O2' _chemical_formula_weight 761.15 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 21.731(4) _cell_length_b 7.2815(15) _cell_length_c 14.910(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.49(3) _cell_angle_gamma 90.00 _cell_volume 2312.0(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10890 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.093 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 836 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9802 _exptl_absorpt_correction_T_max 0.9893 _exptl_absorpt_process_details ; Higash,T(1995) Progrom for Absorption Correcttion. Rigaku Corporation,Tokyo,Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Omega scan' _diffrn_measurement_method 10.0 _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 22042 _diffrn_reflns_av_R_equivalents 0.0683 _diffrn_reflns_av_sigmaI/netI 0.0618 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5280 _reflns_number_gt 2130 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction PROCESS-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0687P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5280 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1580 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_ref 0.1605 _refine_ls_wR_factor_gt 0.1271 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.963 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.08894(9) 0.9367(3) 0.02700(12) 0.0582(5) Uani 1 1 d . . . C2 C 0.13170(10) 1.0750(3) 0.06414(14) 0.0711(6) Uani 1 1 d . . . H2 H 0.1519 1.0684 0.1252 0.085 Uiso 1 1 calc R . . C3 C 0.14387(11) 1.2187(3) 0.01154(16) 0.0822(7) Uani 1 1 d . . . H3 H 0.1723 1.3089 0.0373 0.099 Uiso 1 1 calc R . . C4 C 0.11455(12) 1.2325(3) -0.07990(16) 0.0807(7) Uani 1 1 d . . . H4 H 0.1226 1.3320 -0.1149 0.097 Uiso 1 1 calc R . . C5 C 0.07391(10) 1.0985(3) -0.11747(14) 0.0687(6) Uani 1 1 d . . . H5 H 0.0546 1.1069 -0.1789 0.082 Uiso 1 1 calc R . . C6 C 0.06046(9) 0.9486(3) -0.06613(12) 0.0560(5) Uani 1 1 d . . . C7 C 0.01700(9) 0.8082(3) -0.10908(12) 0.0566(5) Uani 1 1 d . . . C8 C 0.00916(9) 0.6501(3) -0.05236(11) 0.0532(5) Uani 1 1 d . . . C9 C 0.03816(9) 0.6476(3) 0.04138(11) 0.0524(5) Uani 1 1 d . . . C10 C 0.02797(9) 0.4942(3) 0.09128(11) 0.0562(5) Uani 1 1 d . . . H10 H 0.0467 0.4881 0.1530 0.067 Uiso 1 1 calc R . . C11 C 0.09401(9) 0.8041(3) 0.18091(11) 0.0602(5) Uani 1 1 d . . . H11A H 0.0626 0.7414 0.2077 0.072 Uiso 1 1 calc R . . H11B H 0.0939 0.9323 0.1986 0.072 Uiso 1 1 calc R . . C12 C 0.15749(9) 0.7240(3) 0.22124(12) 0.0679(6) Uani 1 1 d . . . H12A H 0.1882 0.7663 0.1868 0.082 Uiso 1 1 calc R . . H12B H 0.1556 0.5911 0.2174 0.082 Uiso 1 1 calc R . . C13 C 0.17727(9) 0.7823(3) 0.32057(13) 0.0727(6) Uani 1 1 d . . . H13A H 0.1819 0.9148 0.3224 0.087 Uiso 1 1 calc R . . H13B H 0.1436 0.7517 0.3521 0.087 Uiso 1 1 calc R . . C14 C 0.23686(11) 0.6989(3) 0.37251(14) 0.0843(7) Uani 1 1 d . . . H14A H 0.2706 0.7274 0.3409 0.101 Uiso 1 1 calc R . . H14B H 0.2321 0.5664 0.3726 0.101 Uiso 1 1 calc R . . C15 C 0.25514(10) 0.7649(3) 0.47060(14) 0.0835(7) Uani 1 1 d . . . H15A H 0.2579 0.8979 0.4706 0.100 Uiso 1 1 calc R . . H15B H 0.2222 0.7315 0.5028 0.100 Uiso 1 1 calc R . . C16 C 0.31641(11) 0.6882(4) 0.52192(15) 0.0943(8) Uani 1 1 d . . . H16A H 0.3129 0.5556 0.5238 0.113 Uiso 1 1 calc R . . H16B H 0.3489 0.7170 0.4880 0.113 Uiso 1 1 calc R . . C17 C 0.33687(10) 0.7572(4) 0.61777(15) 0.0879(7) Uani 1 1 d . . . H17A H 0.3053 0.7237 0.6525 0.105 Uiso 1 1 calc R . . H17B H 0.3388 0.8903 0.6162 0.105 Uiso 1 1 calc R . . C18 C 0.39973(11) 0.6855(4) 0.66732(15) 0.0917(8) Uani 1 1 d . . . H18A H 0.3979 0.5524 0.6683 0.110 Uiso 1 1 calc R . . H18B H 0.4313 0.7198 0.6327 0.110 Uiso 1 1 calc R . . C19 C 0.42037(11) 0.7529(4) 0.76368(15) 0.0869(7) Uani 1 1 d . . . H19A H 0.3889 0.7177 0.7983 0.104 Uiso 1 1 calc R . . H19B H 0.4217 0.8860 0.7626 0.104 Uiso 1 1 calc R . . C20 C 0.48308(11) 0.6838(4) 0.81352(16) 0.0891(7) Uani 1 1 d . . . H20A H 0.4817 0.5507 0.8153 0.107 Uiso 1 1 calc R . . H20B H 0.5146 0.7180 0.7788 0.107 Uiso 1 1 calc R . . C21 C 0.50326(11) 0.7532(3) 0.90903(16) 0.0902(7) Uani 1 1 d . . . H21A H 0.4718 0.7176 0.9437 0.108 Uiso 1 1 calc R . . H21B H 0.5038 0.8864 0.9071 0.108 Uiso 1 1 calc R . . C22 C 0.56608(11) 0.6886(4) 0.95998(16) 0.0913(7) Uani 1 1 d . . . H22A H 0.5657 0.5555 0.9621 0.110 Uiso 1 1 calc R . . H22B H 0.5977 0.7250 0.9259 0.110 Uiso 1 1 calc R . . C23 C 0.58499(11) 0.7597(4) 1.05574(16) 0.0924(8) Uani 1 1 d . . . H23A H 0.5531 0.7234 1.0894 0.111 Uiso 1 1 calc R . . H23B H 0.5850 0.8928 1.0532 0.111 Uiso 1 1 calc R . . C24 C 0.64777(11) 0.6981(4) 1.10913(17) 0.0954(8) Uani 1 1 d . . . H24A H 0.6481 0.5650 1.1118 0.114 Uiso 1 1 calc R . . H24B H 0.6799 0.7354 1.0762 0.114 Uiso 1 1 calc R . . C25 C 0.66466(12) 0.7706(4) 1.20416(18) 0.1090(9) Uani 1 1 d . . . H25A H 0.6324 0.7333 1.2369 0.131 Uiso 1 1 calc R . . H25B H 0.6642 0.9037 1.2013 0.131 Uiso 1 1 calc R . . C26 C 0.72716(14) 0.7109(4) 1.2585(2) 0.1363(12) Uani 1 1 d . . . H26A H 0.7274 0.5798 1.2656 0.204 Uiso 1 1 calc R . . H26B H 0.7343 0.7681 1.3176 0.204 Uiso 1 1 calc R . . H26C H 0.7597 0.7464 1.2269 0.204 Uiso 1 1 calc R . . N1 N 0.07515(7) 0.7927(2) 0.08059(9) 0.0563(4) Uani 1 1 d . . . O1 O -0.01081(7) 0.81995(18) -0.18979(8) 0.0701(4) 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 0.0670(13) 0.0499(13) 0.0603(11) 0.0017(9) 0.0187(10) 0.0045(10) C2 0.0736(15) 0.0644(15) 0.0737(13) 0.0022(11) 0.0109(11) -0.0042(12) C3 0.0858(17) 0.0650(17) 0.0970(17) 0.0031(13) 0.0211(14) -0.0141(13) C4 0.0995(18) 0.0599(15) 0.0888(16) 0.0131(12) 0.0337(14) -0.0059(14) C5 0.0862(16) 0.0564(14) 0.0690(12) 0.0103(11) 0.0288(11) 0.0053(12) C6 0.0664(13) 0.0498(12) 0.0553(11) 0.0027(9) 0.0203(10) 0.0060(10) C7 0.0709(13) 0.0522(13) 0.0488(11) 0.0031(9) 0.0172(10) 0.0100(10) C8 0.0662(13) 0.0474(12) 0.0484(10) 0.0027(8) 0.0172(9) 0.0052(10) C9 0.0620(12) 0.0496(12) 0.0462(10) 0.0007(8) 0.0125(9) 0.0056(10) C10 0.0726(13) 0.0526(12) 0.0431(9) 0.0023(9) 0.0106(9) 0.0049(11) C11 0.0750(13) 0.0585(13) 0.0469(10) -0.0043(8) 0.0117(9) -0.0010(11) C12 0.0697(14) 0.0681(15) 0.0625(12) 0.0001(10) 0.0049(10) 0.0041(11) C13 0.0678(14) 0.0840(17) 0.0645(12) -0.0007(11) 0.0090(11) -0.0064(12) C14 0.0814(16) 0.0882(18) 0.0778(15) 0.0017(12) 0.0023(12) 0.0023(14) C15 0.0789(16) 0.1015(19) 0.0662(14) 0.0018(12) 0.0046(12) -0.0108(14) C16 0.0926(18) 0.104(2) 0.0793(16) 0.0002(13) -0.0003(13) 0.0025(16) C17 0.0785(16) 0.106(2) 0.0759(15) 0.0041(13) 0.0076(12) -0.0054(15) C18 0.0826(16) 0.103(2) 0.0838(16) 0.0057(13) 0.0038(13) 0.0074(15) C19 0.0790(16) 0.097(2) 0.0812(15) 0.0022(13) 0.0076(13) 0.0027(14) C20 0.0787(16) 0.0934(19) 0.0897(16) 0.0059(13) 0.0036(13) 0.0079(15) C21 0.0803(16) 0.100(2) 0.0857(16) 0.0020(14) 0.0041(13) 0.0060(15) C22 0.0847(17) 0.0911(19) 0.0925(17) 0.0039(13) 0.0041(13) 0.0097(15) C23 0.0823(17) 0.095(2) 0.0945(17) 0.0008(13) 0.0035(14) 0.0077(14) C24 0.0892(18) 0.0895(19) 0.1008(19) 0.0067(14) 0.0031(14) 0.0122(15) C25 0.102(2) 0.114(2) 0.102(2) -0.0056(16) -0.0010(16) 0.0115(18) C26 0.117(2) 0.140(3) 0.130(3) 0.005(2) -0.0284(19) 0.026(2) N1 0.0665(10) 0.0542(11) 0.0481(8) 0.0011(7) 0.0112(7) -0.0030(8) O1 0.1010(11) 0.0581(9) 0.0501(8) 0.0057(6) 0.0122(7) 0.0032(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 N1 1.387(2) . ? C1 C6 1.406(2) . ? C1 C2 1.407(3) . ? C2 C3 1.365(3) . ? C3 C4 1.389(3) . ? C4 C5 1.359(3) . ? C5 C6 1.397(3) . ? C6 C7 1.452(3) . ? C7 O1 1.2374(19) . ? C7 C8 1.458(3) . ? C8 C10 1.380(2) 3_565 ? C8 C9 1.414(2) . ? C9 C10 1.384(2) . ? C9 N1 1.385(2) . ? C10 C8 1.380(2) 3_565 ? C11 N1 1.472(2) . ? C11 C12 1.508(3) . ? C12 C13 1.518(2) . ? C13 C14 1.499(3) . ? C14 C15 1.516(3) . ? C15 C16 1.505(3) . ? C16 C17 1.496(3) . ? C17 C18 1.511(3) . ? C18 C19 1.500(3) . ? C19 C20 1.503(3) . ? C20 C21 1.492(3) . ? C21 C22 1.500(3) . ? C22 C23 1.497(3) . ? C23 C24 1.504(3) . ? C24 C25 1.488(3) . ? C25 C26 1.501(3) . ? 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 N1 C1 C6 120.82(18) . . ? N1 C1 C2 121.06(18) . . ? C6 C1 C2 118.12(19) . . ? C3 C2 C1 120.7(2) . . ? C2 C3 C4 121.1(2) . . ? C5 C4 C3 119.1(2) . . ? C4 C5 C6 121.6(2) . . ? C5 C6 C1 119.35(19) . . ? C5 C6 C7 119.84(18) . . ? C1 C6 C7 120.81(18) . . ? O1 C7 C6 121.94(17) . . ? O1 C7 C8 121.87(18) . . ? C6 C7 C8 116.18(17) . . ? C10 C8 C9 120.92(17) 3_565 . ? C10 C8 C7 118.88(17) 3_565 . ? C9 C8 C7 120.18(18) . . ? C10 C9 N1 122.04(16) . . ? C10 C9 C8 117.00(17) . . ? N1 C9 C8 120.96(17) . . ? C8 C10 C9 122.08(17) 3_565 . ? N1 C11 C12 115.50(16) . . ? C11 C12 C13 109.85(17) . . ? C14 C13 C12 116.01(19) . . ? C13 C14 C15 113.8(2) . . ? C16 C15 C14 114.1(2) . . ? C17 C16 C15 115.2(2) . . ? C16 C17 C18 114.8(2) . . ? C19 C18 C17 115.1(2) . . ? C18 C19 C20 115.7(2) . . ? C21 C20 C19 115.1(2) . . ? C20 C21 C22 116.2(2) . . ? C23 C22 C21 115.1(2) . . ? C22 C23 C24 116.7(2) . . ? C25 C24 C23 115.1(2) . . ? C24 C25 C26 115.9(3) . . ? C9 N1 C1 120.51(15) . . ? C9 N1 C11 119.51(15) . . ? C1 N1 C11 119.63(16) . . ? 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 C5 H5 O1 0.93 2.53 3.342(3) 145.9 2_554 C11 H11A O1 0.97 2.46 3.387(2) 159.6 4_576 C11 H11B O1 0.97 2.54 3.298(2) 135.3 3_575 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.123 _refine_diff_density_min -0.133 _refine_diff_density_rms 0.027 #===END data_b _database_code_depnum_ccdc_archive 'CCDC 700175' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H76 N2 O2' _chemical_formula_weight 761.15 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.912(3) _cell_length_b 9.830(2) _cell_length_c 15.129(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.41(3) _cell_angle_gamma 90.00 _cell_volume 2290.1(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13227 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.44 _exptl_crystal_description BLOCK _exptl_crystal_colour red _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.104 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 836 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9709 _exptl_absorpt_correction_T_max 0.9892 _exptl_absorpt_process_details ; Higash,T(1995) Progrom for Absorption Correcttion. Rigaku Corporation,Tokyo,Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Omega scan' _diffrn_measurement_method 10.0 _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 21151 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.44 _reflns_number_total 5207 _reflns_number_gt 2757 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction PROCESS-AUTO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0568P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5207 _refine_ls_number_parameters 401 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0949 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1222 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.39989(9) -0.22777(13) 0.12135(10) 0.0370(3) Uani 1 1 d . . . C2 C 0.35970(10) -0.27395(16) 0.18141(12) 0.0468(4) Uani 1 1 d . . . C3 C 0.32944(12) -0.40473(17) 0.17318(13) 0.0544(5) Uani 1 1 d . . . C4 C 0.33811(12) -0.49586(18) 0.10716(13) 0.0577(5) Uani 1 1 d . . . C5 C 0.37553(11) -0.45266(15) 0.04737(12) 0.0498(4) Uani 1 1 d . . . C6 C 0.40542(9) -0.31830(13) 0.05212(10) 0.0393(4) Uani 1 1 d . . . C7 C 0.44174(10) -0.27548(14) -0.01559(10) 0.0409(4) Uani 1 1 d . . . C8 C 0.47141(9) -0.13366(13) -0.00599(10) 0.0345(3) Uani 1 1 d . . . C9 C 0.46589(9) -0.04784(13) 0.06617(9) 0.0346(3) Uani 1 1 d . . . C10 C 0.49467(10) 0.08575(13) 0.06948(10) 0.0379(4) Uani 1 1 d . . . H10 H 0.4910 0.1447 0.1157 0.045 Uiso 1 1 calc R . . C11 C 0.43527(11) -0.00861(15) 0.21095(11) 0.0395(4) Uani 1 1 d . . . C12 C 0.35336(11) 0.07524(16) 0.18602(12) 0.0442(4) Uani 1 1 d . . . C13 C 0.35943(11) 0.16458(17) 0.27040(12) 0.0480(4) Uani 1 1 d . . . C14 C 0.27497(11) 0.23557(17) 0.25468(13) 0.0481(4) Uani 1 1 d . . . C15 C 0.28062(12) 0.32214(18) 0.34005(13) 0.0511(4) Uani 1 1 d . . . C16 C 0.19688(13) 0.39557(19) 0.32409(14) 0.0544(5) Uani 1 1 d . . . C17 C 0.20025(13) 0.4728(2) 0.41235(14) 0.0585(5) Uani 1 1 d . . . C18 C 0.11513(13) 0.5434(2) 0.39510(14) 0.0593(5) Uani 1 1 d . . . C19 C 0.11547(14) 0.6205(2) 0.48221(15) 0.0630(5) Uani 1 1 d . . . C20 C 0.02974(13) 0.6903(2) 0.46316(15) 0.0610(5) Uani 1 1 d . . . C21 C 0.03024(13) 0.7685(2) 0.54941(15) 0.0617(5) Uani 1 1 d . . . C22 C -0.05489(13) 0.8375(2) 0.53361(14) 0.0591(5) Uani 1 1 d . . . C23 C -0.05010(13) 0.9141(2) 0.62288(14) 0.0602(5) Uani 1 1 d . . . C24 C -0.13336(12) 0.9861(2) 0.61121(14) 0.0570(5) Uani 1 1 d . . . C25 C -0.12506(13) 1.0643(2) 0.70130(15) 0.0623(5) Uani 1 1 d . . . C26 C -0.20723(15) 1.1389(3) 0.6903(2) 0.0742(6) Uani 1 1 d . . . H2 H 0.3527(10) -0.2150(14) 0.2293(11) 0.052(4) Uiso 1 1 d . . . H3 H 0.3029(11) -0.4327(17) 0.2161(12) 0.074(5) Uiso 1 1 d . . . H4 H 0.3161(11) -0.5887(17) 0.1012(12) 0.068(5) Uiso 1 1 d . . . H5 H 0.3861(11) -0.5159(16) 0.0002(12) 0.068(5) Uiso 1 1 d . . . H11A H 0.4883(9) 0.0533(13) 0.2286(9) 0.037(4) Uiso 1 1 d . . . H12A H 0.3429(10) 0.1345(14) 0.1286(11) 0.050(4) Uiso 1 1 d . . . H13A H 0.4063(10) 0.2331(14) 0.2833(11) 0.052(4) Uiso 1 1 d . . . H14A H 0.2521(11) 0.2924(16) 0.1942(13) 0.067(5) Uiso 1 1 d . . . H15A H 0.3295(12) 0.3915(16) 0.3555(12) 0.069(5) Uiso 1 1 d . . . H16A H 0.1809(12) 0.458(2) 0.2639(14) 0.090(6) Uiso 1 1 d . . . H17A H 0.2134(12) 0.4062(19) 0.4664(14) 0.084(6) Uiso 1 1 d . . . H18A H 0.1011(11) 0.6088(16) 0.3382(13) 0.065(5) Uiso 1 1 d . . . H19A H 0.1618(12) 0.6896(18) 0.5035(13) 0.070(6) Uiso 1 1 d . . . H20A H 0.0137(12) 0.7529(19) 0.4080(14) 0.081(6) Uiso 1 1 d . . . H21A H 0.0804(14) 0.838(2) 0.5707(14) 0.093(7) Uiso 1 1 d . . . H22A H -0.0722(11) 0.9039(17) 0.4754(13) 0.071(5) Uiso 1 1 d . . . H23A H 0.0020(13) 0.9842(19) 0.6406(12) 0.083(6) Uiso 1 1 d . . . H24A H -0.1483(12) 1.0515(18) 0.5537(13) 0.074(6) Uiso 1 1 d . . . H25A H -0.0753(12) 1.1315(17) 0.7180(12) 0.071(6) Uiso 1 1 d . . . H26A H -0.2249(14) 1.203(2) 0.6359(16) 0.098(8) Uiso 1 1 d . . . H11B H 0.4441(9) -0.0663(13) 0.2655(10) 0.041(4) Uiso 1 1 d . . . H12B H 0.2995(10) 0.0126(14) 0.1667(10) 0.050(4) Uiso 1 1 d . . . H13B H 0.3786(11) 0.1106(15) 0.3330(12) 0.064(5) Uiso 1 1 d . . . H14B H 0.2298(10) 0.1674(16) 0.2416(11) 0.056(5) Uiso 1 1 d . . . H15B H 0.2999(10) 0.2661(15) 0.3975(12) 0.057(5) Uiso 1 1 d . . . H16B H 0.1506(12) 0.3305(17) 0.3036(13) 0.065(5) Uiso 1 1 d . . . H17B H 0.2494(12) 0.5411(18) 0.4307(12) 0.069(6) Uiso 1 1 d . . . H18B H 0.0671(11) 0.4746(17) 0.3760(12) 0.068(6) Uiso 1 1 d . . . H19B H 0.1315(13) 0.556(2) 0.5420(15) 0.098(7) Uiso 1 1 d . . . H20B H -0.0163(12) 0.6214(18) 0.4467(12) 0.076(6) Uiso 1 1 d . . . H21B H 0.0495(12) 0.7066(19) 0.6064(15) 0.084(6) Uiso 1 1 d . . . H22B H -0.1016(12) 0.7663(18) 0.5135(13) 0.075(6) Uiso 1 1 d . . . H23B H -0.0327(12) 0.8493(18) 0.6799(14) 0.081(6) Uiso 1 1 d . . . H24B H -0.1826(12) 0.9195(16) 0.5963(12) 0.061(5) Uiso 1 1 d . . . H25B H -0.1072(12) 0.9977(18) 0.7645(14) 0.094(6) Uiso 1 1 d . . . H26B H -0.2001(14) 1.193(2) 0.7515(17) 0.112(8) Uiso 1 1 d . . . H26C H -0.2585(15) 1.076(2) 0.6757(15) 0.101(8) Uiso 1 1 d . . . N1 N 0.43306(8) -0.09664(11) 0.13083(8) 0.0378(3) Uani 1 1 d . . . O1 O 0.44620(8) -0.35221(10) -0.07774(8) 0.0608(4) 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 0.0384(9) 0.0412(8) 0.0339(8) 0.0048(6) 0.0173(7) 0.0009(6) C2 0.0505(10) 0.0523(10) 0.0467(10) 0.0068(8) 0.0293(9) 0.0016(8) C3 0.0584(12) 0.0598(11) 0.0538(11) 0.0111(9) 0.0320(10) -0.0073(8) C4 0.0692(13) 0.0514(11) 0.0535(11) 0.0050(8) 0.0264(10) -0.0149(9) C5 0.0624(12) 0.0447(9) 0.0432(10) 0.0008(7) 0.0228(9) -0.0083(8) C6 0.0433(9) 0.0406(8) 0.0349(8) 0.0017(6) 0.0172(7) -0.0024(6) C7 0.0503(10) 0.0402(8) 0.0342(8) -0.0014(7) 0.0193(8) -0.0006(7) C8 0.0392(9) 0.0375(7) 0.0303(8) 0.0005(6) 0.0179(7) 0.0017(6) C9 0.0367(9) 0.0404(8) 0.0304(8) 0.0020(6) 0.0175(7) 0.0016(6) C10 0.0461(9) 0.0407(8) 0.0315(8) -0.0036(6) 0.0208(7) 0.0015(7) C11 0.0499(10) 0.0451(9) 0.0313(8) -0.0009(7) 0.0246(8) -0.0007(8) C12 0.0491(11) 0.0490(9) 0.0396(9) -0.0012(7) 0.0235(8) 0.0033(8) C13 0.0514(11) 0.0514(10) 0.0472(10) -0.0065(8) 0.0263(9) 0.0020(8) C14 0.0514(11) 0.0478(9) 0.0516(11) -0.0036(8) 0.0278(9) 0.0017(8) C15 0.0538(12) 0.0517(10) 0.0535(11) -0.0011(9) 0.0276(10) 0.0081(9) C16 0.0544(12) 0.0578(11) 0.0556(12) -0.0067(9) 0.0271(10) 0.0071(9) C17 0.0538(13) 0.0653(12) 0.0584(12) -0.0073(10) 0.0253(10) 0.0128(10) C18 0.0567(13) 0.0635(12) 0.0591(12) -0.0064(10) 0.0252(10) 0.0118(10) C19 0.0626(13) 0.0683(12) 0.0604(13) -0.0080(10) 0.0278(11) 0.0147(10) C20 0.0611(13) 0.0644(12) 0.0629(13) -0.0036(10) 0.0310(11) 0.0127(10) C21 0.0641(13) 0.0673(12) 0.0607(13) -0.0020(10) 0.0329(11) 0.0155(11) C22 0.0593(13) 0.0629(12) 0.0591(13) -0.0034(10) 0.0284(11) 0.0116(10) C23 0.0568(13) 0.0701(12) 0.0582(12) -0.0040(10) 0.0284(11) 0.0099(10) C24 0.0512(12) 0.0647(12) 0.0576(12) -0.0054(9) 0.0249(10) 0.0056(10) C25 0.0559(13) 0.0755(12) 0.0616(13) -0.0126(10) 0.0304(11) 0.0032(10) C26 0.0611(14) 0.0870(15) 0.0819(17) -0.0161(14) 0.0367(13) 0.0107(12) N1 0.0477(8) 0.0400(7) 0.0330(7) 0.0006(5) 0.0241(6) -0.0002(5) O1 0.1016(10) 0.0447(6) 0.0543(7) -0.0123(5) 0.0506(7) -0.0127(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 N1 1.3893(17) . ? C1 C6 1.4067(18) . ? C1 C2 1.4155(19) . ? C2 C3 1.370(2) . ? C3 C4 1.394(2) . ? C4 C5 1.368(2) . ? C5 C6 1.4053(19) . ? C6 C7 1.4574(19) . ? C7 O1 1.2318(16) . ? C7 C8 1.4683(19) . ? C8 C10 1.3890(18) 3_655 ? C8 C9 1.4129(18) . ? C9 C10 1.3941(19) . ? C9 N1 1.3944(16) . ? C10 C8 1.3890(18) 3_655 ? C11 N1 1.4770(17) . ? C11 C12 1.519(2) . ? C12 C13 1.518(2) . ? C13 C14 1.518(2) . ? C14 C15 1.516(2) . ? C15 C16 1.517(2) . ? C16 C17 1.516(2) . ? C17 C18 1.521(2) . ? C18 C19 1.518(2) . ? C19 C20 1.520(2) . ? C20 C21 1.512(2) . ? C21 C22 1.518(2) . ? C22 C23 1.519(2) . ? C23 C24 1.519(2) . ? C24 C25 1.520(2) . ? C25 C26 1.518(3) . ? 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 N1 C1 C6 121.03(12) . . ? N1 C1 C2 120.78(13) . . ? C6 C1 C2 118.19(13) . . ? C3 C2 C1 120.19(16) . . ? C2 C3 C4 121.48(16) . . ? C5 C4 C3 119.25(16) . . ? C4 C5 C6 120.85(16) . . ? C5 C6 C1 119.96(13) . . ? C5 C6 C7 118.86(13) . . ? C1 C6 C7 121.18(12) . . ? O1 C7 C6 122.43(13) . . ? O1 C7 C8 122.05(13) . . ? C6 C7 C8 115.51(12) . . ? C10 C8 C9 120.66(12) 3_655 . ? C10 C8 C7 118.39(12) 3_655 . ? C9 C8 C7 120.96(12) . . ? C10 C9 N1 122.22(12) . . ? C10 C9 C8 117.17(12) . . ? N1 C9 C8 120.61(12) . . ? C8 C10 C9 122.17(12) 3_655 . ? N1 C11 C12 113.76(13) . . ? C13 C12 C11 111.56(14) . . ? C14 C13 C12 113.72(15) . . ? C15 C14 C13 113.62(15) . . ? C14 C15 C16 113.92(16) . . ? C17 C16 C15 113.90(16) . . ? C16 C17 C18 112.90(16) . . ? C19 C18 C17 114.53(17) . . ? C18 C19 C20 113.55(17) . . ? C21 C20 C19 113.67(17) . . ? C20 C21 C22 115.13(17) . . ? C21 C22 C23 112.51(17) . . ? C22 C23 C24 114.90(17) . . ? C23 C24 C25 113.17(17) . . ? C26 C25 C24 113.89(18) . . ? C1 N1 C9 120.51(11) . . ? C1 N1 C11 120.03(11) . . ? C9 N1 C11 119.46(11) . . ? 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 C11 H11B O1 0.960(14) 2.490(14) 3.4113(19) 160.7(11) 4_556 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.158 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.036