Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2002 data_cryt2b _database_code_CSD 175319 _audit_creation_method SHELXL-97 _chemical_name_systematic ; bis(2-methyl-1,4-naphthylene)-22-crown-6 ; _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Liu, Zhong-Li' 'Chow, Yuan L.' 'Shao, Xiangfeng' 'Yang, Li' 'Zhang, Wei' _publ_contact_author_name 'Prof Zhong-Li Liu' _publ_contact_author_address ; National Laboratory of Applied Organic Chemistry Lanzhou Univeristy Lanzhou Gansu 730000 CHINA ; _publ_contact_author_email 'LIUZL@LZU.EDU.CN' _publ_section_title ; Photochemical reactions of naphthaquinone diazides in Cyclic Ethers ; _chemical_name_common ? _chemical_melting_point 187-188 _chemical_formula_moiety ? _chemical_formula_sum 'C30 H32 O6' _chemical_formula_weight 488.2193 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' '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 'C2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 20.531(4) _cell_length_b 7.4340(10) _cell_length_c 16.899(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.34(3) _cell_angle_gamma 90.00 _cell_volume 2487.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10 _cell_measurement_theta_max 20 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'NONIUS' CAD4' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0.2 _diffrn_reflns_number 4315 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2259 _reflns_number_gt 1405 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 (Enraf-Nonius)' _computing_cell_refinement 'CAD4 (Enraf-Nonius)' _computing_data_reduction 'MOLEN PC' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SIEMENS SHELXTL PC' _computing_publication_material ? _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^)+(0.0662P)^2^+1.0159P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(5) _refine_ls_number_reflns 2259 _refine_ls_number_parameters 325 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0845 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1391 _refine_ls_wR_factor_gt 0.1007 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 1.466 _refine_ls_shift/su_mean 0.373 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 O1 O 0.6191(3) 1.1955(10) 0.5420(4) 0.0555(19) Uani 1 1 d . . . O2 O 0.6360(4) 0.8164(10) 0.4871(5) 0.062(2) Uani 1 1 d . . . O3 O 0.4919(4) 0.7031(12) 0.4175(4) 0.057(2) Uani 1 1 d . . . O4 O 0.3544(3) 1.2972(12) 0.3618(4) 0.058(2) Uani 1 1 d . . . O5 O 0.2107(4) 1.1785(11) 0.2937(5) 0.063(2) Uani 1 1 d . . . O6 O 0.2260(3) 0.8043(10) 0.2380(5) 0.0528(19) Uani 1 1 d . . . C1 C 0.6356(6) 1.0314(15) 0.5898(7) 0.064(3) Uani 1 1 d . . . H1A H 0.6224 1.0458 0.6399 0.080 Uiso 1 1 d R . . H1B H 0.6837 1.0156 0.6042 0.080 Uiso 1 1 d R . . C2 C 0.6049(5) 0.8653(16) 0.5486(7) 0.056(3) Uani 1 1 d . . . H2A H 0.6086 0.7709 0.5883 0.080 Uiso 1 1 d R . . H2B H 0.5578 0.8875 0.5242 0.080 Uiso 1 1 d R . . C3 C 0.6122(6) 0.6593(16) 0.4474(8) 0.065(3) Uani 1 1 d . . . H3A H 0.6050 0.5756 0.4875 0.080 Uiso 1 1 d R . . H3B H 0.6463 0.6097 0.4244 0.080 Uiso 1 1 d R . . C4 C 0.5459(6) 0.6812(14) 0.3816(8) 0.057(3) Uani 1 1 d . . . H4A H 0.5486 0.7815 0.3468 0.080 Uiso 1 1 d R . . H4B H 0.5387 0.5741 0.3486 0.080 Uiso 1 1 d R . . C5 C 0.3019(5) 1.3203(15) 0.4034(7) 0.053(3) Uani 1 1 d . . . H5A H 0.3116 1.4191 0.4413 0.080 Uiso 1 1 d R . . H5B H 0.2983 1.2122 0.4330 0.080 Uiso 1 1 d R . . C6 C 0.2385(5) 1.3439(13) 0.3385(8) 0.057(3) Uani 1 1 d . . . H6A H 0.2052 1.3943 0.3625 0.080 Uiso 1 1 d R . . H6B H 0.2473 1.4296 0.3001 0.080 Uiso 1 1 d R . . C7 C 0.2423(6) 1.1301(16) 0.2309(8) 0.066(3) Uani 1 1 d . . . H7A H 0.2900 1.1137 0.2536 0.080 Uiso 1 1 d R . . H7B H 0.2355 1.2270 0.1920 0.080 Uiso 1 1 d R . . C8 C 0.2102(6) 0.9606(16) 0.1898(7) 0.066(3) Uani 1 1 d . . . H8A H 0.1620 0.9757 0.1729 0.080 Uiso 1 1 d R . . H8B H 0.2253 0.9418 0.1413 0.080 Uiso 1 1 d R . . C9 C 0.4681(5) 1.2340(14) 0.3670(6) 0.047(2) Uani 1 1 d . . . C10 C 0.4523(5) 1.2296(15) 0.2804(6) 0.054(3) Uani 1 1 d . . . H10A H 0.4060 1.2473 0.2504 0.080 Uiso 1 1 d R . . C11 C 0.5003(6) 1.1981(16) 0.2409(7) 0.062(3) Uani 1 1 d . . . H11A H 0.4877 1.1963 0.1820 0.080 Uiso 1 1 d R . . C12 C 0.5684(6) 1.1721(17) 0.2861(7) 0.060(3) Uani 1 1 d . . . H12A H 0.6102 1.1234 0.2664 0.050 Uiso 1 1 d R . . C13 C 0.5837(5) 1.1752(15) 0.3710(6) 0.052(3) Uani 1 1 d . . . H13A H 0.6293 1.1560 0.4028 0.080 Uiso 1 1 d R . . C14 C 0.5355(5) 1.2063(12) 0.4141(6) 0.040(2) Uani 1 1 d . . . C15 C 0.5520(5) 1.2171(13) 0.5001(6) 0.044(2) Uani 1 1 d . . . C16 C 0.5049(6) 1.2642(15) 0.5412(6) 0.050(3) Uani 1 1 d . . . C17 C 0.4361(5) 1.2877(14) 0.4920(6) 0.049(3) Uani 1 1 d . . . H17A H 0.4022 1.3114 0.5202 0.080 Uiso 1 1 d R . . C18 C 0.4180(5) 1.2744(15) 0.4125(6) 0.049(3) Uani 1 1 d . . . C19 C 0.2942(5) 0.7783(13) 0.2787(6) 0.044(2) Uani 1 1 d . . . C20 C 0.3425(6) 0.7380(14) 0.2406(6) 0.049(3) Uani 1 1 d . . . C21 C 0.4085(6) 0.7156(15) 0.2840(6) 0.051(3) Uani 1 1 d . . . H21A H 0.4420 0.6870 0.2557 0.080 Uiso 1 1 d R . . C22 C 0.4277(5) 0.7281(13) 0.3713(6) 0.044(2) Uani 1 1 d . . . C23 C 0.3786(5) 0.7624(13) 0.4119(6) 0.042(2) Uani 1 1 d . . . C24 C 0.3112(6) 0.7923(13) 0.3671(6) 0.046(3) Uani 1 1 d . . . C25 C 0.2601(5) 0.8267(14) 0.4089(6) 0.052(3) Uani 1 1 d . . . H25A H 0.2144 0.8518 0.3791 0.080 Uiso 1 1 d R . . C26 C 0.2779(6) 0.8260(18) 0.4914(8) 0.063(3) Uani 1 1 d . . . H26A H 0.2439 0.8428 0.5204 0.080 Uiso 1 1 d R . . C27 C 0.3430(7) 0.7953(18) 0.5368(7) 0.067(3) Uani 1 1 d . . . H27A H 0.3529 0.7964 0.5956 0.080 Uiso 1 1 d R . . C28 C 0.3942(6) 0.7695(15) 0.4984(7) 0.057(3) Uani 1 1 d . . . H28A H 0.4397 0.7542 0.5313 0.080 Uiso 1 1 d R . . C29 C 0.5212(7) 1.3016(18) 0.6308(7) 0.069(3) Uani 1 1 d . . . H29A H 0.5685 1.2791 0.6535 0.080 Uiso 1 1 d R . . H29B H 0.5114 1.4248 0.6402 0.080 Uiso 1 1 d R . . H29C H 0.4955 1.2241 0.6565 0.080 Uiso 1 1 d R . . C30 C 0.3246(5) 0.7193(19) 0.1466(7) 0.068(3) Uani 1 1 d . . . H30A H 0.2772 0.7388 0.1227 0.080 Uiso 1 1 d R . . H30B H 0.3501 0.8051 0.1246 0.080 Uiso 1 1 d R . . H30C H 0.3364 0.5998 0.1339 0.080 Uiso 1 1 d R . . 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 0.047(4) 0.059(4) 0.059(5) -0.002(4) 0.011(4) -0.004(3) O2 0.054(4) 0.051(4) 0.078(6) 0.000(4) 0.012(4) 0.004(3) O3 0.046(5) 0.076(6) 0.050(4) 0.000(4) 0.013(4) -0.002(4) O4 0.037(4) 0.072(6) 0.062(4) 0.007(4) 0.010(3) 0.003(3) O5 0.046(4) 0.058(5) 0.086(6) -0.015(4) 0.022(4) -0.016(4) O6 0.043(4) 0.049(4) 0.059(4) -0.003(4) 0.000(4) -0.004(3) C1 0.070(6) 0.058(6) 0.056(7) 0.012(5) 0.003(6) 0.001(5) C2 0.051(5) 0.062(7) 0.051(6) 0.013(5) 0.007(5) 0.012(5) C3 0.041(5) 0.064(7) 0.085(8) -0.001(6) 0.008(5) 0.003(5) C4 0.055(6) 0.045(6) 0.074(7) 0.002(5) 0.023(6) -0.014(5) C5 0.038(5) 0.058(6) 0.064(6) -0.005(5) 0.017(5) 0.004(4) C6 0.053(5) 0.032(5) 0.090(7) -0.003(5) 0.023(5) -0.005(4) C7 0.075(7) 0.047(6) 0.074(8) 0.010(6) 0.016(6) -0.003(5) C8 0.054(5) 0.072(7) 0.058(7) -0.009(6) -0.010(5) 0.014(5) C9 0.052(6) 0.041(5) 0.047(6) 0.012(4) 0.014(5) 0.007(4) C10 0.054(6) 0.067(7) 0.039(6) 0.009(5) 0.010(5) 0.007(5) C11 0.072(8) 0.066(8) 0.050(7) -0.010(6) 0.021(6) -0.013(6) C12 0.067(7) 0.060(7) 0.061(7) -0.008(5) 0.030(6) 0.001(6) C13 0.041(5) 0.051(6) 0.061(7) 0.005(5) 0.010(5) 0.005(4) C14 0.043(5) 0.028(5) 0.053(6) 0.005(4) 0.022(4) 0.001(4) C15 0.042(6) 0.040(5) 0.050(6) 0.000(4) 0.014(5) 0.002(4) C16 0.057(6) 0.049(6) 0.050(6) -0.001(5) 0.021(5) -0.010(5) C17 0.036(5) 0.054(6) 0.063(7) 0.006(5) 0.023(5) -0.002(4) C18 0.037(5) 0.060(7) 0.051(6) 0.006(5) 0.016(5) -0.013(5) C19 0.043(6) 0.039(5) 0.046(6) -0.001(4) 0.003(5) -0.013(4) C20 0.048(6) 0.052(6) 0.044(6) -0.002(5) 0.008(5) -0.003(5) C21 0.057(6) 0.059(7) 0.039(5) -0.005(5) 0.017(5) -0.001(5) C22 0.046(6) 0.039(5) 0.046(6) 0.000(4) 0.008(5) 0.003(4) C23 0.044(5) 0.038(5) 0.045(5) -0.011(4) 0.016(5) -0.013(4) C24 0.051(6) 0.041(6) 0.043(6) -0.005(4) 0.010(5) -0.011(5) C25 0.062(6) 0.043(6) 0.059(7) -0.007(5) 0.033(5) -0.002(5) C26 0.061(7) 0.075(9) 0.061(7) -0.002(6) 0.030(6) 0.004(6) C27 0.075(8) 0.089(9) 0.040(6) 0.003(6) 0.022(6) 0.009(7) C28 0.056(6) 0.058(6) 0.053(7) -0.008(5) 0.010(5) -0.014(5) C29 0.088(7) 0.066(5) 0.052(6) 0.002(4) 0.017(5) 0.001(5) C30 0.045(5) 0.109(8) 0.051(6) -0.022(5) 0.014(5) -0.009(5) _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 O1 C15 1.381(12) . ? O1 C1 1.453(13) . ? O2 C3 1.371(14) . ? O2 C2 1.402(14) . ? O3 C22 1.355(12) . ? O3 C4 1.407(13) . ? O4 C18 1.369(12) . ? O4 C5 1.445(12) . ? O5 C7 1.428(15) . ? O5 C6 1.477(13) . ? O6 C19 1.400(12) . ? O6 C8 1.408(14) . ? C1 C2 1.475(16) . ? C3 C4 1.521(18) . ? C5 C6 1.474(17) . ? C7 C8 1.504(16) . ? C9 C14 1.416(14) . ? C9 C10 1.413(15) . ? C9 C18 1.469(14) . ? C10 C11 1.348(17) . ? C11 C12 1.419(17) . ? C12 C13 1.385(16) . ? C13 C14 1.394(14) . ? C14 C15 1.405(15) . ? C15 C16 1.377(14) . ? C16 C17 1.447(15) . ? C16 C29 1.487(16) . ? C17 C18 1.300(15) . ? C19 C20 1.351(15) . ? C19 C24 1.444(15) . ? C20 C21 1.369(15) . ? C20 C30 1.540(16) . ? C21 C22 1.426(14) . ? C22 C23 1.385(14) . ? C23 C28 1.411(15) . ? C23 C24 1.408(15) . ? C24 C25 1.434(15) . ? C25 C26 1.345(16) . ? C26 C27 1.374(17) . ? C27 C28 1.387(18) . ? 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 C15 O1 C1 115.9(8) . . ? C3 O2 C2 114.3(10) . . ? C22 O3 C4 121.7(8) . . ? C18 O4 C5 114.9(8) . . ? C7 O5 C6 113.7(8) . . ? C19 O6 C8 116.5(8) . . ? O1 C1 C2 115.6(8) . . ? O2 C2 C1 110.2(9) . . ? O2 C3 C4 113.6(10) . . ? O3 C4 C3 110.6(10) . . ? O4 C5 C6 106.2(9) . . ? O5 C6 C5 115.3(9) . . ? O5 C7 C8 108.9(9) . . ? O6 C8 C7 114.7(8) . . ? C14 C9 C10 120.1(9) . . ? C14 C9 C18 116.8(8) . . ? C10 C9 C18 123.1(9) . . ? C11 C10 C9 121.2(11) . . ? C10 C11 C12 120.2(11) . . ? C13 C12 C11 118.5(10) . . ? C12 C13 C14 123.1(10) . . ? C13 C14 C9 116.9(9) . . ? C13 C14 C15 122.6(9) . . ? C9 C14 C15 120.4(9) . . ? C16 C15 O1 120.6(9) . . ? C16 C15 C14 121.8(9) . . ? O1 C15 C14 117.3(9) . . ? C15 C16 C17 116.7(9) . . ? C15 C16 C29 124.2(10) . . ? C17 C16 C29 119.0(10) . . ? C18 C17 C16 123.6(10) . . ? C17 C18 O4 127.0(10) . . ? C17 C18 C9 120.5(9) . . ? O4 C18 C9 112.4(8) . . ? C20 C19 O6 124.1(9) . . ? C20 C19 C24 120.1(9) . . ? O6 C19 C24 115.8(9) . . ? C19 C20 C21 121.3(9) . . ? C19 C20 C30 120.4(10) . . ? C21 C20 C30 118.3(9) . . ? C20 C21 C22 120.6(10) . . ? O3 C22 C23 117.7(8) . . ? O3 C22 C21 123.2(9) . . ? C23 C22 C21 119.1(10) . . ? C22 C23 C28 121.6(10) . . ? C22 C23 C24 120.2(9) . . ? C28 C23 C24 118.2(9) . . ? C23 C24 C25 120.3(9) . . ? C23 C24 C19 118.6(9) . . ? C25 C24 C19 121.0(10) . . ? C26 C25 C24 118.6(10) . . ? C25 C26 C27 122.4(10) . . ? C28 C27 C26 120.5(11) . . ? C27 C28 C23 119.8(11) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.184 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.050