# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_2Br-tetraketo _database_code_depnum_ccdc_archive 'CCDC 847344' #TrackingRef 'web_deposit_cif_file_0_MartinBaumgarten_1317888006.2Br-tetraketo.cif' _audit_creation_date 07-10-17 _audit_creation_method CRYSTALS_ver_12.39 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.5579(4) _cell_length_b 8.2137(5) _cell_length_c 10.2782(5) _cell_angle_alpha 74.6441(13) _cell_angle_beta 85.9937(12) _cell_angle_gamma 86.1229(12) _cell_volume 531.87(5) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C12 H10 Br1 O3 # Dc = 1.76 Fooo = 282.00 Mu = 38.51 M = 282.11 # Found Formula = C12 H10 Br1 O3 # Dc = 1.76 FOOO = 282.00 Mu = 38.51 M = 282.11 _chemical_formula_sum 'C12 H10 Br1 O3' _chemical_formula_moiety 'C12 H10 Br1 O3' _chemical_compound_source ? _chemical_formula_weight 282.11 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.38 _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 282 _exptl_absorpt_coefficient_mu 3.851 # Sheldrick geometric approximatio 0.38 0.73 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_absorpt_correction_T_min 0.56 _exptl_absorpt_correction_T_max 0.73 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 3330 _reflns_number_total 1944 _diffrn_reflns_av_R_equivalents 0.050 # Number of reflections with Friedels Law is 1944 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2964 _diffrn_reflns_theta_min 4.118 _diffrn_reflns_theta_max 29.499 _diffrn_measured_fraction_theta_max 0.658 _diffrn_reflns_theta_full 25.074 _diffrn_measured_fraction_theta_full 0.735 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -8 _reflns_limit_h_max 9 _reflns_limit_k_min -9 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.74 _refine_diff_density_max 0.57 _refine_ls_number_reflns 1673 _refine_ls_number_restraints 0 _refine_ls_number_parameters 145 #_refine_ls_R_factor_ref 0.0300 _refine_ls_wR_factor_ref 0.0301 _refine_ls_goodness_of_fit_ref 1.1503 #_reflns_number_all 1944 _refine_ls_R_factor_all 0.0407 _refine_ls_wR_factor_all 0.0303 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 1673 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_gt 0.0301 _refine_ls_shift/su_max 0.055520 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 47.5 -50.8 29.4 ; # Insert your own references if required - in alphabetical order 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Br1 Br 0.64125(4) 0.75485(4) 0.17467(3) 0.0214 1.0000 Uani . . . . . . C1 C 0.4162(3) 0.6633(4) 0.1176(3) 0.0165 1.0000 Uani . . . . . . C2 C 0.3888(3) 0.4922(4) 0.1576(3) 0.0181 1.0000 Uani . . . . . . C3 C 0.2236(3) 0.4271(4) 0.1123(3) 0.0168 1.0000 Uani . . . . . . C4 C 0.0863(3) 0.5351(3) 0.0235(2) 0.0153 1.0000 Uani . . . . . . C5 C 0.1209(3) 0.7076(3) -0.0156(3) 0.0165 1.0000 Uani . . . . . . C6 C 0.2847(3) 0.7731(4) 0.0305(3) 0.0176 1.0000 Uani . . . . . . C7 C 0.2001(3) 0.2433(4) 0.1562(3) 0.0201 1.0000 Uani . . . . . . C8 C -0.0171(3) 0.8296(4) -0.1092(3) 0.0182 1.0000 Uani . . . . . . C11 C 0.9239(4) 0.3607(5) 0.4129(3) 0.0294 1.0000 Uani . . . . . . C12 C 0.7714(5) 0.3134(6) 0.5364(4) 0.0410 1.0000 Uani . . . . . . C13 C 0.6331(4) 0.1907(5) 0.5021(3) 0.0309 1.0000 Uani . . . . . . C14 C 0.7506(4) 0.1406(4) 0.3842(3) 0.0250 1.0000 Uani . . . . . . O1 O 0.3213(3) 0.1461(3) 0.2256(3) 0.0394 1.0000 Uani . . . . . . O2 O 0.0091(3) 0.9792(3) -0.1477(2) 0.0218 1.0000 Uani . . . . . . O11 O 0.8501(3) 0.2920(3) 0.3124(2) 0.0256 1.0000 Uani . . . . . . H21 H 0.4814 0.4183 0.2157 0.0237 1.0000 Uiso R . . . . . H61 H 0.3057 0.8908 0.0022 0.0210 1.0000 Uiso R . . . . . H111 H 1.0572 0.3138 0.4358 0.0385 1.0000 Uiso R . . . . . H112 H 0.9280 0.4800 0.3802 0.0385 1.0000 Uiso R . . . . . H121 H 0.8418 0.2607 0.6156 0.0513 1.0000 Uiso R . . . . . H122 H 0.6944 0.4107 0.5490 0.0513 1.0000 Uiso R . . . . . H131 H 0.6138 0.0952 0.5769 0.0400 1.0000 Uiso R . . . . . H132 H 0.5040 0.2446 0.4763 0.0400 1.0000 Uiso R . . . . . H141 H 0.8478 0.0497 0.4151 0.0315 1.0000 Uiso R . . . . . H142 H 0.6589 0.1092 0.3285 0.0315 1.0000 Uiso 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 Br1 0.01584(11) 0.02483(17) 0.02629(15) -0.00996(12) -0.00376(7) -0.00479(8) C1 0.0134(9) 0.0199(14) 0.0189(13) -0.0092(12) 0.0002(7) -0.0039(8) C2 0.0159(9) 0.0209(14) 0.0183(13) -0.0058(12) -0.0017(8) -0.0021(8) C3 0.0131(9) 0.0211(15) 0.0172(12) -0.0063(12) -0.0014(7) -0.0031(8) C4 0.0126(9) 0.0188(14) 0.0161(12) -0.0073(11) -0.0008(7) -0.0019(8) C5 0.0148(9) 0.0175(14) 0.0184(13) -0.0070(11) -0.0004(8) -0.0019(8) C6 0.0148(9) 0.0209(15) 0.0189(13) -0.0082(12) -0.0006(8) -0.0021(8) C7 0.0181(10) 0.0189(15) 0.0250(14) -0.0072(12) -0.0046(8) -0.0030(8) C8 0.0171(10) 0.0183(15) 0.0208(13) -0.0079(12) -0.0006(8) -0.0009(8) C11 0.0304(13) 0.0321(18) 0.0290(16) -0.0110(15) -0.0022(10) -0.0110(11) C12 0.0441(17) 0.051(2) 0.0329(19) -0.0188(19) 0.0059(13) -0.0186(15) C13 0.0338(14) 0.036(2) 0.0217(15) -0.0042(15) 0.0027(10) -0.0119(12) C14 0.0212(11) 0.0248(16) 0.0285(15) -0.0046(14) -0.0043(9) -0.0043(9) O1 0.0326(10) 0.0230(13) 0.0576(16) 0.0045(12) -0.0240(10) -0.0045(8) O2 0.0227(8) 0.0155(11) 0.0281(11) -0.0059(9) -0.0034(7) -0.0032(6) O11 0.0273(9) 0.0286(12) 0.0221(10) -0.0073(10) 0.0000(7) -0.0095(8) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 . C1 . 1.895(3) yes C1 . C2 . 1.377(4) yes C1 . C6 . 1.390(3) yes C2 . C3 . 1.399(3) yes C2 . H21 . 0.950 no C3 . C4 . 1.418(3) yes C3 . C7 . 1.472(4) yes C4 . C4 2_565 1.469(5) yes C4 . C5 . 1.396(4) yes C5 . C6 . 1.397(3) yes C5 . C8 . 1.496(3) yes C6 . H61 . 0.950 no C7 . C8 2_565 1.537(4) yes C7 . O1 . 1.213(3) yes C8 . O2 . 1.207(4) yes C11 . C12 . 1.541(4) yes C11 . O11 . 1.427(4) yes C11 . H111 . 0.950 no C11 . H112 . 0.950 no C12 . C13 . 1.523(5) yes C12 . H121 . 0.950 no C12 . H122 . 0.950 no C13 . C14 . 1.524(4) yes C13 . H131 . 0.950 no C13 . H132 . 0.950 no C14 . O11 . 1.440(3) yes C14 . H141 . 0.950 no C14 . H142 . 0.950 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Br1 . C1 . C2 . 120.70(18) yes Br1 . C1 . C6 . 118.1(2) yes C2 . C1 . C6 . 121.2(2) yes C1 . C2 . C3 . 119.7(2) yes C1 . C2 . H21 . 120.334 no C3 . C2 . H21 . 119.962 no C2 . C3 . C4 . 120.7(2) yes C2 . C3 . C7 . 118.2(2) yes C4 . C3 . C7 . 121.1(2) yes C4 2_565 C4 . C3 . 120.1(3) yes C4 2_565 C4 . C5 . 122.2(3) yes C3 . C4 . C5 . 117.7(2) yes C4 . C5 . C6 . 121.7(2) yes C4 . C5 . C8 . 120.9(2) yes C6 . C5 . C8 . 117.4(2) yes C5 . C6 . C1 . 119.0(3) yes C5 . C6 . H61 . 120.222 no C1 . C6 . H61 . 120.783 no C8 2_565 C7 . C3 . 118.8(2) yes C8 2_565 C7 . O1 . 118.4(3) yes C3 . C7 . O1 . 122.8(3) yes C7 2_565 C8 . C5 . 116.9(2) yes C7 2_565 C8 . O2 . 119.9(2) yes C5 . C8 . O2 . 123.2(2) yes C12 . C11 . O11 . 106.1(3) yes C12 . C11 . H111 . 110.652 no O11 . C11 . H111 . 110.275 no C12 . C11 . H112 . 110.458 no O11 . C11 . H112 . 109.820 no H111 . C11 . H112 . 109.466 no C11 . C12 . C13 . 104.4(3) yes C11 . C12 . H121 . 110.425 no C13 . C12 . H121 . 110.868 no C11 . C12 . H122 . 110.780 no C13 . C12 . H122 . 110.789 no H121 . C12 . H122 . 109.465 no C12 . C13 . C14 . 103.4(2) yes C12 . C13 . H131 . 110.764 no C14 . C13 . H131 . 111.230 no C12 . C13 . H132 . 110.786 no C14 . C13 . H132 . 111.138 no H131 . C13 . H132 . 109.467 no C13 . C14 . O11 . 103.7(3) yes C13 . C14 . H141 . 111.277 no O11 . C14 . H141 . 111.169 no C13 . C14 . H142 . 110.408 no O11 . C14 . H142 . 110.754 no H141 . C14 . H142 . 109.468 no C14 . O11 . C11 . 106.2(2) yes data_kawa1 _database_code_depnum_ccdc_archive 'CCDC 857532' #TrackingRef '8575_web_deposit_cif_file_0_MartinBaumgarten_1323356323.kawa1.cif' _audit_creation_date 07-11-08 _audit_creation_method CRYSTALS_ver_12.39 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.3552(5) _cell_length_b 6.6260(4) _cell_length_c 11.1029(5) _cell_angle_alpha 90 _cell_angle_beta 101.3731(12) _cell_angle_gamma 90 _cell_volume 674.73(6) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z x+1/2,-y+1/2,z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C9 H2 N1 O2 # Dc = 1.54 Fooo = 316.00 Mu = 1.12 M = 156.12 # Found Formula = C9 H2 N1 O2 # Dc = 1.54 FOOO = 316.00 Mu = 1.12 M = 156.12 _chemical_formula_sum 'C9 H2 N1 O2' _chemical_formula_moiety 'C9 H2 N1 O2' _chemical_compound_source ? _chemical_formula_weight 156.12 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_min 0.21 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_max 0.42 _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.112 # Sheldrick geometric approximatio 0.97 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_cell_refinement 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 9424 _reflns_number_total 1841 _diffrn_reflns_av_R_equivalents 0.071 # Number of reflections with Friedels Law is 1841 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 1879 _diffrn_reflns_theta_min 6.549 _diffrn_reflns_theta_max 29.494 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.724 _diffrn_measured_fraction_theta_full 0.985 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.27 _refine_diff_density_max 0.36 _refine_ls_number_reflns 958 _refine_ls_number_restraints 0 _refine_ls_number_parameters 109 #_refine_ls_R_factor_ref 0.0425 _refine_ls_wR_factor_ref 0.0514 _refine_ls_goodness_of_fit_ref 1.0867 #_reflns_number_all 1841 _refine_ls_R_factor_all 0.0905 _refine_ls_wR_factor_all 0.0526 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 958 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_gt 0.0514 _refine_ls_shift/su_max 0.000240 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 18.0 -7.08 16.0 ; # Insert your own references if required - in alphabetical order 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.39120(16) 0.9407(2) 0.18452(13) 0.0244 1.0000 Uani . . . . . . C1 C 0.52452(18) 0.4827(3) 0.06652(18) 0.0142 1.0000 Uani . . . . . . C7 C 0.41794(19) 0.8149(3) 0.11370(17) 0.0160 1.0000 Uani . . . . . . C5 C 0.6449(2) 0.2712(3) 0.23663(17) 0.0186 1.0000 Uani . . . . . . C2 C 0.49756(18) 0.6255(3) 0.15239(17) 0.0153 1.0000 Uani . . . . . . C6 C 0.59826(18) 0.3035(3) 0.11055(16) 0.0152 1.0000 Uani . . . . . . C3 C 0.54535(19) 0.5939(3) 0.27790(18) 0.0185 1.0000 Uani . . . . . . C4 C 0.61949(19) 0.4172(3) 0.32005(17) 0.0199 1.0000 Uani . . . . . . N1 N 0.7089(2) 0.3770(3) 0.55423(18) 0.0331 1.0000 Uani . . . . . . C9 C 0.6696(2) 0.3912(3) 0.4504(2) 0.0248 1.0000 Uani . . . . . . O2 O 0.68347(15) -0.0155(2) 0.05975(13) 0.0211 1.0000 Uani . . . . . . C8 C 0.62869(19) 0.1464(3) 0.02505(18) 0.0165 1.0000 Uani . . . . . . H51 H 0.6939 0.1497 0.2654 0.0254 1.0000 Uiso R . . . . . H31 H 0.5275 0.6934 0.3348 0.0260 1.0000 Uiso 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 0.0282(7) 0.0236(7) 0.0210(7) -0.0011(6) 0.0044(5) 0.0066(6) C1 0.0133(7) 0.0157(8) 0.0134(7) 0.0019(7) 0.0016(6) -0.0013(6) C7 0.0142(7) 0.0165(8) 0.0165(9) 0.0016(7) 0.0008(6) 0.0006(6) C5 0.0184(7) 0.0182(9) 0.0177(9) 0.0025(7) 0.0000(7) 0.0010(6) C2 0.0149(7) 0.0146(8) 0.0155(8) 0.0002(7) 0.0005(6) -0.0003(6) C6 0.0143(7) 0.0163(8) 0.0144(8) 0.0014(7) 0.0011(6) -0.0017(6) C3 0.0207(8) 0.0198(9) 0.0149(8) -0.0011(7) 0.0034(7) -0.0007(6) C4 0.0212(8) 0.0227(9) 0.0149(9) 0.0019(7) 0.0014(7) -0.0007(7) N1 0.0434(11) 0.0312(11) 0.0224(9) 0.0036(8) 0.0009(8) 0.0053(8) C9 0.0299(10) 0.0231(11) 0.0197(10) -0.0001(8) 0.0011(8) 0.0032(7) O2 0.0201(6) 0.0184(7) 0.0248(7) 0.0040(6) 0.0043(5) 0.0046(5) C8 0.0142(7) 0.0162(8) 0.0191(9) 0.0021(7) 0.0036(6) -0.0001(6) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C7 . 1.205(2) yes C1 . C1 2_665 1.476(4) yes C1 . C2 . 1.401(2) yes C1 . C6 . 1.411(2) yes C7 . C8 2_665 1.538(3) yes C7 . C2 . 1.479(2) yes C5 . C6 . 1.398(3) yes C5 . C4 . 1.392(3) yes C5 . H51 . 0.950 no C2 . C3 . 1.393(3) yes C6 . C8 . 1.474(3) yes C3 . C4 . 1.394(3) yes C3 . H31 . 0.950 no C4 . C9 . 1.442(3) yes N1 . C9 . 1.142(3) yes O2 . C8 . 1.218(2) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 2_665 C1 . C2 . 120.9(2) yes C1 2_665 C1 . C6 . 120.8(2) yes C2 . C1 . C6 . 118.28(16) yes C8 2_665 C7 . O1 . 118.94(16) yes C8 2_665 C7 . C2 . 117.36(15) yes O1 . C7 . C2 . 123.68(16) yes C6 . C5 . C4 . 119.96(17) yes C6 . C5 . H51 . 120.044 no C4 . C5 . H51 . 119.998 no C7 . C2 . C1 . 121.55(15) yes C7 . C2 . C3 . 117.50(16) yes C1 . C2 . C3 . 120.95(16) yes C1 . C6 . C5 . 120.68(17) yes C1 . C6 . C8 . 120.95(15) yes C5 . C6 . C8 . 118.36(16) yes C2 . C3 . C4 . 120.14(17) yes C2 . C3 . H31 . 119.808 no C4 . C3 . H31 . 120.048 no C3 . C4 . C5 . 119.97(16) yes C3 . C4 . C9 . 118.63(17) yes C5 . C4 . C9 . 121.40(18) yes C4 . C9 . N1 . 177.8(2) yes C7 2_665 C8 . C6 . 118.35(14) yes C7 2_665 C8 . O2 . 118.83(17) yes C6 . C8 . O2 . 122.74(17) yes data_omepynme _database_code_depnum_ccdc_archive 'CCDC 857533' #TrackingRef '8576_web_deposit_cif_file_1_MartinBaumgarten_ #1323356323.omepynme.cif' _audit_creation_date 10-12-01 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 16.0033(9) _cell_length_b 6.9362(4) _cell_length_c 20.1144(9) _cell_angle_alpha 90 _cell_angle_beta 112.579(3) _cell_angle_gamma 90 _cell_volume 2061.61(19) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C24 H28 N2 O4 # Dc = 1.32 Fooo = 872.00 Mu = 0.90 M = 408.50 # Found Formula = C24 H28 N2 O4 # Dc = 1.32 FOOO = 872.00 Mu = 0.90 M = 408.50 _chemical_formula_sum 'C24 H28 N2 O4' _chemical_formula_moiety 'C24 H28 N2 O4' _chemical_compound_source ? _chemical_formula_weight 408.50 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_min 0.14 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_max 0.41 _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.090 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 14114 _reflns_number_total 5651 _diffrn_reflns_av_R_equivalents 0.063 # Number of reflections with Friedels Law is 5651 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5945 _diffrn_reflns_theta_min 3.040 _diffrn_reflns_theta_max 29.923 _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 25.136 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _reflns_limit_h_min -22 _reflns_limit_h_max 20 _reflns_limit_k_min 0 _reflns_limit_k_max 9 _reflns_limit_l_min 0 _reflns_limit_l_max 28 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.55 _refine_diff_density_max 0.43 _refine_ls_number_reflns 3257 _refine_ls_number_restraints 0 _refine_ls_number_parameters 272 #_refine_ls_R_factor_ref 0.0510 _refine_ls_wR_factor_ref 0.0448 _refine_ls_goodness_of_fit_ref 0.9882 #_reflns_number_all 5651 _refine_ls_R_factor_all 0.0988 _refine_ls_wR_factor_all 0.1764 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3257 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_gt 0.0448 _refine_ls_shift/su_max 0.000544 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 3.14 3.57 1.35 ; #_publ_section_title # Functionalization of Pyrene: # from a Polycyclic Aromatic Hydrocarbon to Electron- # Donors and Electron-Acceptors #; Chem. Eur. J. #; # Insert your own references if required - in alphabetical order 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.52297(5) 0.40831(11) 0.24904(5) 0.0280 1.0000 Uani . . . . . . C2 C 0.51505(5) 0.32389(11) 0.18513(5) 0.0302 1.0000 Uani . . . . . . C3 C 0.56085(5) 0.14980(12) 0.18566(5) 0.0319 1.0000 Uani . . . . . . C4 C 0.61967(5) 0.06554(12) 0.25113(5) 0.0314 1.0000 Uani . . . . . . C5 C 0.62823(5) 0.15012(11) 0.31666(5) 0.0294 1.0000 Uani . . . . . . C6 C 0.57986(5) 0.31728(11) 0.31453(5) 0.0281 1.0000 Uani . . . . . . C7 C 0.58900(5) 0.40801(11) 0.38188(5) 0.0290 1.0000 Uani . . . . . . C8 C 0.54570(5) 0.58062(11) 0.38104(5) 0.0296 1.0000 Uani . . . . . . C9 C 0.48608(5) 0.67126(11) 0.31541(5) 0.0292 1.0000 Uani . . . . . . C10 C 0.47624(5) 0.58199(11) 0.25004(5) 0.0284 1.0000 Uani . . . . . . C11 C 0.41872(5) 0.67046(11) 0.18500(5) 0.0306 1.0000 Uani . . . . . . C12 C 0.41312(6) 0.58114(12) 0.11818(5) 0.0327 1.0000 Uani . . . . . . C13 C 0.45474(6) 0.40924(12) 0.11825(5) 0.0325 1.0000 Uani . . . . . . C14 C 0.44103(5) 0.83850(11) 0.31550(5) 0.0319 1.0000 Uani . . . . . . C15 C 0.38188(6) 0.92676(12) 0.25061(5) 0.0333 1.0000 Uani . . . . . . C16 C 0.37568(6) 0.83992(12) 0.18555(5) 0.0329 1.0000 Uani . . . . . . C17 C 0.71636(5) -0.21133(13) 0.31690(5) 0.0370 1.0000 Uani . . . . . . C18 C 0.65054(6) -0.21650(14) 0.18471(5) 0.0398 1.0000 Uani . . . . . . C19 C 0.35100(6) 1.19108(13) 0.31634(6) 0.0414 1.0000 Uani . . . . . . C20 C 0.28279(6) 1.19360(13) 0.18313(6) 0.0425 1.0000 Uani . . . . . . C21 C 0.59332(5) 0.25216(14) 0.48448(4) 0.0320 1.0000 Uani . . . . . . C22 C 0.64469(5) 0.74079(14) 0.48894(5) 0.0372 1.0000 Uani . . . . . . C23 C 0.40714(6) 0.74638(17) 0.00962(5) 0.0433 1.0000 Uani . . . . . . C24 C 0.35999(6) 0.25663(16) 0.01433(4) 0.0392 1.0000 Uani . . . . . . O1 O 0.64349(3) 0.31770(8) 0.44564(3) 0.0314 1.0000 Uani . . . . . . O2 O 0.55547(4) 0.66785(8) 0.44574(3) 0.0330 1.0000 Uani . . . . . . O3 O 0.35595(4) 0.67231(9) 0.05375(4) 0.0376 1.0000 Uani . . . . . . O4 O 0.44529(4) 0.31513(9) 0.05295(4) 0.0374 1.0000 Uani . . . . . . N1 N 0.66900(5) -0.10106(11) 0.25011(4) 0.0352 1.0000 Uani . . . . . . N2 N 0.33181(5) 1.08938(10) 0.25046(5) 0.0377 1.0000 Uani . . . . . . H31 H 0.5521 0.0892 0.1411 0.0377 1.0000 Uiso R . . . . . H51 H 0.6654 0.0931 0.3612 0.0404 1.0000 Uiso R . . . . . H141 H 0.4490 0.8979 0.3601 0.0432 1.0000 Uiso R . . . . . H161 H 0.3401 0.8995 0.1411 0.0392 1.0000 Uiso R . . . . . H171 H 0.7462 -0.3198 0.3073 0.0464 1.0000 Uiso R . . . . . H172 H 0.7597 -0.1286 0.3502 0.0464 1.0000 Uiso R . . . . . H173 H 0.6744 -0.2536 0.3367 0.0464 1.0000 Uiso R . . . . . H181 H 0.6902 -0.3241 0.1943 0.0422 1.0000 Uiso R . . . . . H182 H 0.6601 -0.1350 0.1503 0.0422 1.0000 Uiso R . . . . . H183 H 0.5896 -0.2603 0.1663 0.0422 1.0000 Uiso R . . . . . H191 H 0.3114 1.2985 0.3077 0.0608 1.0000 Uiso R . . . . . H192 H 0.4119 1.2349 0.3344 0.0608 1.0000 Uiso R . . . . . H193 H 0.3422 1.1080 0.3506 0.0608 1.0000 Uiso R . . . . . H201 H 0.2522 1.3007 0.1928 0.0559 1.0000 Uiso R . . . . . H202 H 0.3246 1.2379 0.1634 0.0559 1.0000 Uiso R . . . . . H203 H 0.2400 1.1101 0.1497 0.0559 1.0000 Uiso R . . . . . H211 H 0.6331 0.1918 0.5273 0.0360 1.0000 Uiso R . . . . . H212 H 0.5640 0.3578 0.4965 0.0360 1.0000 Uiso R . . . . . H213 H 0.5493 0.1618 0.4565 0.0360 1.0000 Uiso R . . . . . H221 H 0.6425 0.7968 0.5313 0.0405 1.0000 Uiso R . . . . . H222 H 0.6870 0.6377 0.5017 0.0405 1.0000 Uiso R . . . . . H223 H 0.6628 0.8355 0.4630 0.0405 1.0000 Uiso R . . . . . H231 H 0.3650 0.8057 -0.0325 0.0757 1.0000 Uiso R . . . . . H232 H 0.4522 0.8372 0.0357 0.0757 1.0000 Uiso R . . . . . H233 H 0.4348 0.6401 -0.0037 0.0757 1.0000 Uiso R . . . . . H241 H 0.3591 0.1954 -0.0282 0.0323 1.0000 Uiso R . . . . . H242 H 0.3204 0.3645 0.0017 0.0323 1.0000 Uiso R . . . . . H243 H 0.3407 0.1680 0.0416 0.0323 1.0000 Uiso 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 C1 0.0184(3) 0.0322(4) 0.0369(4) -0.0025(3) 0.0144(3) -0.0006(3) C2 0.0225(4) 0.0356(4) 0.0373(5) -0.0024(3) 0.0169(3) -0.0004(3) C3 0.0244(4) 0.0371(4) 0.0398(5) -0.0045(3) 0.0186(4) 0.0003(3) C4 0.0222(4) 0.0352(4) 0.0416(5) -0.0047(3) 0.0174(3) 0.0017(3) C5 0.0186(3) 0.0331(4) 0.0395(4) -0.0039(3) 0.0144(3) 0.0014(3) C6 0.0175(3) 0.0322(4) 0.0376(4) -0.0032(3) 0.0138(3) 0.0003(3) C7 0.0179(3) 0.0329(4) 0.0375(4) -0.0042(3) 0.0121(3) 0.0012(3) C8 0.0194(3) 0.0324(4) 0.0382(5) -0.0050(3) 0.0124(3) 0.0007(3) C9 0.0194(3) 0.0312(4) 0.0390(5) -0.0030(3) 0.0134(3) 0.0004(3) C10 0.0189(3) 0.0315(4) 0.0377(4) -0.0015(3) 0.0140(3) -0.0005(3) C11 0.0227(4) 0.0333(4) 0.0389(5) 0.0013(3) 0.0152(3) -0.0003(3) C12 0.0261(4) 0.0380(4) 0.0376(5) 0.0022(3) 0.0162(3) -0.0001(3) C13 0.0266(4) 0.0387(4) 0.0368(5) -0.0008(3) 0.0174(4) -0.0007(3) C14 0.0228(4) 0.0311(4) 0.0439(5) -0.0028(3) 0.0153(4) 0.0018(3) C15 0.0244(4) 0.0317(4) 0.0457(5) 0.0005(3) 0.0156(4) 0.0025(3) C16 0.0247(4) 0.0333(4) 0.0428(5) 0.0027(3) 0.0154(4) 0.0014(3) C17 0.0252(4) 0.0382(5) 0.0510(5) -0.0048(4) 0.0185(4) 0.0064(3) C18 0.0336(4) 0.0423(5) 0.0506(5) -0.0088(4) 0.0240(4) 0.0047(4) C19 0.0340(4) 0.0339(4) 0.0579(6) -0.0031(4) 0.0193(4) 0.0064(3) C20 0.0343(5) 0.0354(4) 0.0585(6) 0.0065(4) 0.0187(4) 0.0071(3) C21 0.0226(3) 0.0387(4) 0.0348(4) -0.0026(4) 0.0111(3) 0.0048(3) C22 0.0255(3) 0.0390(4) 0.0437(4) -0.0108(4) 0.0094(3) 0.0009(4) C23 0.0417(4) 0.0506(5) 0.0434(5) 0.0086(5) 0.0229(4) 0.0016(5) C24 0.0363(4) 0.0484(5) 0.0347(4) -0.0023(5) 0.0156(3) -0.0002(4) O1 0.0194(3) 0.0368(3) 0.0374(3) -0.0044(2) 0.0102(2) 0.00274(19) O2 0.0234(3) 0.0360(3) 0.0391(3) -0.0071(2) 0.0116(2) 0.0024(2) O3 0.0322(3) 0.0441(3) 0.0394(4) 0.0055(3) 0.0170(3) 0.0011(2) O4 0.0342(3) 0.0467(4) 0.0368(3) -0.0017(3) 0.0196(3) 0.0001(2) N1 0.0252(3) 0.0384(4) 0.0472(4) -0.0060(3) 0.0197(3) 0.0037(3) N2 0.0292(4) 0.0329(4) 0.0525(5) 0.0011(3) 0.0172(4) 0.0048(3) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.3734(11) yes C1 . C6 . 1.4289(12) yes C1 . C10 . 1.4222(10) yes C2 . C3 . 1.4105(11) yes C2 . C13 . 1.4473(12) yes C3 . C4 . 1.4176(13) yes C3 . H31 . 0.950 no C4 . C5 . 1.4006(12) yes C4 . N1 . 1.4041(10) yes C5 . C6 . 1.3856(10) yes C5 . H51 . 0.950 no C6 . C7 . 1.4493(11) yes C7 . C8 . 1.3802(10) yes C7 . O1 . 1.3924(10) yes C8 . C9 . 1.4427(12) yes C8 . O2 . 1.3884(10) yes C9 . C10 . 1.4064(12) yes C9 . C14 . 1.3661(11) yes C10 . C11 . 1.4180(12) yes C11 . C12 . 1.4512(12) yes C11 . C16 . 1.3645(11) yes C12 . C13 . 1.3654(11) yes C12 . O3 . 1.4164(11) yes C13 . O4 . 1.4220(10) yes C14 . C15 . 1.4232(13) yes C14 . H141 . 0.950 no C15 . C16 . 1.4092(13) yes C15 . N2 . 1.3829(10) yes C16 . H161 . 0.950 no C17 . N1 . 1.4773(12) yes C17 . H171 . 0.950 no C17 . H172 . 0.950 no C17 . H173 . 0.950 no C18 . N1 . 1.4699(11) yes C18 . H181 . 0.950 no C18 . H182 . 0.950 no C18 . H183 . 0.950 no C19 . N2 . 1.4266(12) yes C19 . H191 . 0.950 no C19 . H192 . 0.950 no C19 . H193 . 0.950 no C20 . N2 . 1.4685(12) yes C20 . H201 . 0.950 no C20 . H202 . 0.950 no C20 . H203 . 0.950 no C21 . O1 . 1.3939(9) yes C21 . H211 . 0.950 no C21 . H212 . 0.950 no C21 . H213 . 0.950 no C22 . O2 . 1.4481(9) yes C22 . H221 . 0.950 no C22 . H222 . 0.950 no C22 . H223 . 0.950 no C23 . O3 . 1.5105(10) yes C23 . H231 . 0.950 no C23 . H232 . 0.950 no C23 . H233 . 0.950 no C24 . O4 . 1.3480(10) yes C24 . H241 . 0.950 no C24 . H242 . 0.950 no C24 . H243 . 0.950 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C6 . 118.14(7) yes C2 . C1 . C10 . 120.95(8) yes C6 . C1 . C10 . 120.90(7) yes C1 . C2 . C3 . 119.80(8) yes C1 . C2 . C13 . 118.98(7) yes C3 . C2 . C13 . 121.09(8) yes C2 . C3 . C4 . 121.18(8) yes C2 . C3 . H31 . 118.9 no C4 . C3 . H31 . 119.9 no C3 . C4 . C5 . 119.45(7) yes C3 . C4 . N1 . 120.15(8) yes C5 . C4 . N1 . 120.40(8) yes C4 . C5 . C6 . 118.02(8) yes C4 . C5 . H51 . 120.8 no C6 . C5 . H51 . 121.1 no C1 . C6 . C5 . 123.29(8) yes C1 . C6 . C7 . 118.02(7) yes C5 . C6 . C7 . 118.67(8) yes C6 . C7 . C8 . 119.68(7) yes C6 . C7 . O1 . 117.93(7) yes C8 . C7 . O1 . 122.38(7) yes C7 . C8 . C9 . 122.81(8) yes C7 . C8 . O2 . 119.42(7) yes C9 . C8 . O2 . 117.69(7) yes C8 . C9 . C10 . 117.45(7) yes C8 . C9 . C14 . 122.20(8) yes C10 . C9 . C14 . 120.35(9) yes C1 . C10 . C9 . 121.03(8) yes C1 . C10 . C11 . 120.81(7) yes C9 . C10 . C11 . 118.16(7) yes C10 . C11 . C12 . 117.20(7) yes C10 . C11 . C16 . 121.08(9) yes C12 . C11 . C16 . 121.56(9) yes C11 . C12 . C13 . 121.01(8) yes C11 . C12 . O3 . 116.44(7) yes C13 . C12 . O3 . 122.30(8) yes C2 . C13 . C12 . 120.60(8) yes C2 . C13 . O4 . 117.86(7) yes C12 . C13 . O4 . 121.41(8) yes C9 . C14 . C15 . 121.98(9) yes C9 . C14 . H141 . 119.4 no C15 . C14 . H141 . 118.7 no C14 . C15 . C16 . 116.91(7) yes C14 . C15 . N2 . 122.25(8) yes C16 . C15 . N2 . 120.83(8) yes C15 . C16 . C11 . 121.33(9) yes C15 . C16 . H161 . 119.4 no C11 . C16 . H161 . 119.3 no N1 . C17 . H171 . 110.3 no N1 . C17 . H172 . 108.0 no H171 . C17 . H172 . 109.5 no N1 . C17 . H173 . 110.1 no H171 . C17 . H173 . 109.5 no H172 . C17 . H173 . 109.5 no N1 . C18 . H181 . 111.0 no N1 . C18 . H182 . 107.1 no H181 . C18 . H182 . 109.5 no N1 . C18 . H183 . 110.3 no H181 . C18 . H183 . 109.5 no H182 . C18 . H183 . 109.5 no N2 . C19 . H191 . 109.1 no N2 . C19 . H192 . 109.7 no H191 . C19 . H192 . 109.5 no N2 . C19 . H193 . 109.6 no H191 . C19 . H193 . 109.5 no H192 . C19 . H193 . 109.5 no N2 . C20 . H201 . 109.4 no N2 . C20 . H202 . 109.4 no H201 . C20 . H202 . 109.5 no N2 . C20 . H203 . 109.7 no H201 . C20 . H203 . 109.5 no H202 . C20 . H203 . 109.5 no O1 . C21 . H211 . 108.8 no O1 . C21 . H212 . 109.7 no H211 . C21 . H212 . 109.5 no O1 . C21 . H213 . 109.8 no H211 . C21 . H213 . 109.5 no H212 . C21 . H213 . 109.5 no O2 . C22 . H221 . 108.3 no O2 . C22 . H222 . 109.6 no H221 . C22 . H222 . 109.5 no O2 . C22 . H223 . 110.5 no H221 . C22 . H223 . 109.5 no H222 . C22 . H223 . 109.5 no O3 . C23 . H231 . 108.2 no O3 . C23 . H232 . 111.6 no H231 . C23 . H232 . 109.5 no O3 . C23 . H233 . 108.6 no H231 . C23 . H233 . 109.5 no H232 . C23 . H233 . 109.5 no O4 . C24 . H241 . 108.4 no O4 . C24 . H242 . 109.9 no H241 . C24 . H242 . 109.5 no O4 . C24 . H243 . 110.1 no H241 . C24 . H243 . 109.5 no H242 . C24 . H243 . 109.5 no C21 . O1 . C7 . 111.78(6) yes C22 . O2 . C8 . 116.42(6) yes C23 . O3 . C12 . 112.58(6) yes C13 . O4 . C24 . 113.29(6) yes C17 . N1 . C18 . 112.86(7) yes C17 . N1 . C4 . 120.52(7) yes C18 . N1 . C4 . 122.72(7) yes C20 . N2 . C19 . 117.48(7) yes C20 . N2 . C15 . 120.49(8) yes C19 . N2 . C15 . 118.91(8) yes data_py4ome2ntol _database_code_depnum_ccdc_archive 'CCDC 857534' #TrackingRef '8577_web_deposit_cif_file_2_MartinBaumgarten_ #1323356323.py4omentol.cif' _audit_creation_date 11-10-06 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 13.9727(4) _cell_length_b 9.7974(3) _cell_length_c 14.0930(4) _cell_angle_alpha 90 _cell_angle_beta 99.9701(18) _cell_angle_gamma 90 _cell_volume 1900.14(10) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C48 H42 N2 O4 # Dc = 1.24 Fooo = 756.00 Mu = 0.79 M = 355.44 # Found Formula = C48 H44 N2 O4 # Dc = 1.25 FOOO = 756.00 Mu = 0.79 M = 356.44 _chemical_formula_sum 'C48 H44 N2 O4' _chemical_formula_moiety 'C48 H44 N2 O4' _chemical_compound_source ? _chemical_formula_weight 712.89 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_min 0.18 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_max 0.45 _exptl_crystal_density_diffrn 1.246 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 756 _exptl_absorpt_coefficient_mu 0.079 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_absorpt_correction_T_min 0.68 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 19112 _reflns_number_total 5296 _diffrn_reflns_av_R_equivalents 0.065 # Number of reflections with Friedels Law is 5296 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5315 _diffrn_reflns_theta_min 5.109 _diffrn_reflns_theta_max 29.551 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.960 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -19 _reflns_limit_h_max 19 _reflns_limit_k_min 0 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.39 _refine_diff_density_max 0.37 _refine_ls_number_reflns 3672 _refine_ls_number_restraints 0 _refine_ls_number_parameters 244 #_refine_ls_R_factor_ref 0.0549 _refine_ls_wR_factor_ref 0.0712 _refine_ls_goodness_of_fit_ref 1.1721 #_reflns_number_all 5296 _refine_ls_R_factor_all 0.0774 _refine_ls_wR_factor_all 0.0780 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 3672 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_gt 0.0712 _refine_ls_shift/su_max 0.003603 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 3.44 1.66 2.80 ; #_publ_section_title # Functionalization of Pyrene: from a Polycyclic Aromatic #Hydrocarbon to Electron- #Donors and Electron-Acceptors #; Chem. Eur. J. #; # Insert your own references if required - in alphabetical order 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.01777(8) -0.06888(13) 0.23186(8) 0.0263 1.0000 Uani . . . . . . O2 O -0.19915(8) -0.00463(14) 0.66139(8) 0.0287 1.0000 Uani . . . . . . C1 C 0.02924(10) -0.03863(15) 0.32872(10) 0.0196 1.0000 Uani . . . . . . C2 C -0.05649(9) -0.04439(14) 0.37257(10) 0.0182 1.0000 Uani . . . . . . C3 C -0.14769(10) -0.07623(15) 0.31916(11) 0.0198 1.0000 Uani . . . . . . C4 C -0.23006(10) -0.08164(14) 0.36359(11) 0.0201 1.0000 Uani . . . . . . C5 C -0.22024(10) -0.05705(15) 0.46277(11) 0.0205 1.0000 Uani . . . . . . C6 C -0.12957(9) -0.02567(14) 0.51744(10) 0.0184 1.0000 Uani . . . . . . C7 C -0.04590(9) -0.01725(14) 0.47263(10) 0.0173 1.0000 Uani . . . . . . C8 C -0.11722(10) 0.00246(15) 0.61909(10) 0.0203 1.0000 Uani . . . . . . C9 C -0.20035(18) -0.1220(3) 0.7212(2) 0.0570 1.0000 Uani . . . . . . C10 C 0.0646(3) -0.1874(3) 0.2099(2) 0.0856 1.0000 Uani . . . . . . C11 C -0.33980(10) -0.08271(15) 0.20779(11) 0.0219 1.0000 Uani . . . . . . C12 C -0.36762(12) -0.18666(16) 0.14135(12) 0.0267 1.0000 Uani . . . . . . C13 C -0.38573(12) -0.15710(17) 0.04317(12) 0.0274 1.0000 Uani . . . . . . C14 C -0.37609(10) -0.02513(17) 0.00976(11) 0.0246 1.0000 Uani . . . . . . C15 C -0.34966(11) 0.07824(16) 0.07750(12) 0.0259 1.0000 Uani . . . . . . C16 C -0.33141(11) 0.04988(16) 0.17546(12) 0.0242 1.0000 Uani . . . . . . C17 C -0.40087(10) -0.15217(16) 0.35317(11) 0.0222 1.0000 Uani . . . . . . C18 C -0.48109(14) -0.0680(2) 0.34808(14) 0.0375 1.0000 Uani . . . . . . C19 C -0.55919(14) -0.1061(3) 0.39088(15) 0.0439 1.0000 Uani . . . . . . C20 C -0.55925(12) -0.2279(2) 0.44020(13) 0.0331 1.0000 Uani . . . . . . C21 C -0.47900(16) -0.3113(2) 0.44394(19) 0.0462 1.0000 Uani . . . . . . C22 C -0.40062(14) -0.27493(19) 0.40099(18) 0.0414 1.0000 Uani . . . . . . C23 C -0.39329(13) 0.0061(2) -0.09648(13) 0.0351 1.0000 Uani . . . . . . C24 C -0.64477(16) -0.2677(3) 0.48696(18) 0.0506 1.0000 Uani . . . . . . N1 N -0.32050(9) -0.11391(15) 0.30850(9) 0.0254 1.0000 Uani . . . . . . H31 H -0.1538 -0.0942 0.2521 0.0278 1.0000 Uiso R . . . . . H51 H -0.2758 -0.0615 0.4931 0.0284 1.0000 Uiso R . . . . . H101 H 0.0407 -0.2087 0.1418 0.0500 1.0000 Uiso R . . . . . H102 H 0.0494 -0.2600 0.2495 0.0991 1.0000 Uiso R . . . . . H103 H 0.1329 -0.1740 0.2203 0.0991 1.0000 Uiso R . . . . . H121 H -0.3746 -0.2774 0.1630 0.0361 1.0000 Uiso R . . . . . H131 H -0.4045 -0.2284 -0.0019 0.0373 1.0000 Uiso R . . . . . H151 H -0.3441 0.1694 0.0560 0.0343 1.0000 Uiso R . . . . . H161 H -0.3134 0.1213 0.2207 0.0327 1.0000 Uiso R . . . . . H181 H -0.4822 0.0169 0.3154 0.0498 1.0000 Uiso R . . . . . H191 H -0.6139 -0.0473 0.3863 0.0553 1.0000 Uiso R . . . . . H211 H -0.4773 -0.3951 0.4781 0.0573 1.0000 Uiso R . . . . . H221 H -0.3465 -0.3345 0.4041 0.0520 1.0000 Uiso R . . . . . H231 H -0.4115 -0.0797 -0.1336 0.0423 1.0000 Uiso R . . . . . H232 H -0.4471 0.0742 -0.1120 0.0423 1.0000 Uiso R . . . . . H233 H -0.3325 0.0444 -0.1144 0.0423 1.0000 Uiso R . . . . . H241 H -0.6321 -0.3587 0.5189 0.0626 1.0000 Uiso R . . . . . H242 H -0.6539 -0.1976 0.5362 0.0626 1.0000 Uiso R . . . . . H243 H -0.7048 -0.2730 0.4369 0.0626 1.0000 Uiso R . . . . . H91 H -0.2611 -0.1215 0.7497 0.0711 1.0000 Uiso R . . . . . H92 H -0.1425 -0.1201 0.7741 0.0711 1.0000 Uiso R . . . . . H93 H -0.1984 -0.2064 0.6817 0.0711 1.0000 Uiso 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 0.0228(5) 0.0363(6) 0.0199(5) -0.0019(4) 0.0036(4) 0.0016(4) O2 0.0157(5) 0.0457(7) 0.0264(5) 0.0009(5) 0.0082(4) -0.0013(5) C1 0.0168(6) 0.0228(7) 0.0194(6) 0.0006(5) 0.0032(5) 0.0003(5) C2 0.0142(6) 0.0186(6) 0.0216(6) 0.0012(5) 0.0024(5) 0.0004(5) C3 0.0157(6) 0.0213(7) 0.0216(6) 0.0010(5) 0.0010(5) 0.0002(5) C4 0.0138(6) 0.0194(6) 0.0260(7) 0.0034(5) 0.0006(5) -0.0013(5) C5 0.0136(6) 0.0227(6) 0.0249(7) 0.0026(5) 0.0025(5) -0.0016(5) C6 0.0134(6) 0.0189(6) 0.0227(6) 0.0018(5) 0.0027(5) 0.0004(5) C7 0.0130(6) 0.0174(6) 0.0215(6) 0.0014(5) 0.0028(5) 0.0002(4) C8 0.0148(6) 0.0242(7) 0.0226(7) 0.0007(5) 0.0049(5) 0.0006(5) C9 0.0406(11) 0.0701(16) 0.0664(15) 0.0283(13) 0.0267(11) -0.0052(11) C10 0.109(2) 0.081(2) 0.0529(15) -0.0378(14) -0.0255(15) 0.0590(19) C11 0.0152(6) 0.0245(7) 0.0247(7) 0.0028(5) 0.0001(5) -0.0019(5) C12 0.0251(7) 0.0200(7) 0.0328(8) 0.0010(6) -0.0012(6) -0.0024(6) C13 0.0261(7) 0.0249(7) 0.0297(7) -0.0063(6) 0.0007(6) 0.0010(6) C14 0.0173(6) 0.0310(8) 0.0254(7) 0.0006(6) 0.0035(5) 0.0009(5) C15 0.0235(7) 0.0241(7) 0.0286(7) 0.0057(6) 0.0004(6) -0.0032(6) C16 0.0218(6) 0.0212(7) 0.0279(7) -0.0005(5) -0.0003(5) -0.0040(5) C17 0.0150(6) 0.0267(7) 0.0242(7) -0.0006(5) 0.0015(5) -0.0035(5) C18 0.0342(9) 0.0433(10) 0.0370(9) 0.0122(8) 0.0117(7) 0.0138(8) C19 0.0276(8) 0.0641(13) 0.0427(10) 0.0110(9) 0.0134(7) 0.0184(9) C20 0.0202(7) 0.0456(10) 0.0348(8) -0.0105(7) 0.0086(6) -0.0086(7) C21 0.0423(10) 0.0273(9) 0.0771(15) 0.0062(9) 0.0332(10) -0.0049(8) C22 0.0297(9) 0.0284(9) 0.0724(14) 0.0136(9) 0.0263(9) 0.0063(7) C23 0.0304(8) 0.0495(11) 0.0254(8) 0.0017(7) 0.0051(6) 0.0002(8) C24 0.0302(9) 0.0745(16) 0.0523(12) -0.0105(11) 0.0217(9) -0.0128(10) N1 0.0154(5) 0.0341(7) 0.0250(6) 0.0062(5) -0.0010(4) -0.0060(5) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.3788(18) yes O1 . C10 . 1.394(3) yes O2 . C8 . 1.3810(17) yes O2 . C9 . 1.427(3) yes C1 . C8 2_556 1.3655(19) yes C1 . C2 . 1.4410(19) yes C2 . C3 . 1.3984(18) yes C2 . C7 . 1.4174(19) yes C3 . C4 . 1.403(2) yes C3 . H31 . 0.950 no C4 . C5 . 1.401(2) yes C4 . N1 . 1.4000(18) yes C5 . C6 . 1.3983(19) yes C5 . H51 . 0.950 no C6 . C7 . 1.4241(18) yes C6 . C8 . 1.440(2) yes C7 . C7 2_556 1.418(3) yes C9 . H91 . 1.000 no C9 . H92 . 1.000 no C9 . H93 . 1.000 no C10 . H101 . 0.983 no C10 . H102 . 0.950 no C10 . H103 . 0.950 no C11 . C12 . 1.393(2) yes C11 . C16 . 1.388(2) yes C11 . N1 . 1.4310(19) yes C12 . C13 . 1.393(2) yes C12 . H121 . 0.950 no C13 . C14 . 1.390(2) yes C13 . H131 . 0.950 no C14 . C15 . 1.397(2) yes C14 . C23 . 1.506(2) yes C15 . C16 . 1.388(2) yes C15 . H151 . 0.950 no C16 . H161 . 0.950 no C17 . C18 . 1.383(2) yes C17 . C22 . 1.378(2) yes C17 . N1 . 1.4293(18) yes C18 . C19 . 1.386(3) yes C18 . H181 . 0.950 no C19 . C20 . 1.381(3) yes C19 . H191 . 0.950 no C20 . C21 . 1.381(3) yes C20 . C24 . 1.513(3) yes C21 . C22 . 1.386(2) yes C21 . H211 . 0.950 no C22 . H221 . 0.950 no C23 . H231 . 1.000 no C23 . H232 . 1.000 no C23 . H233 . 1.000 no C24 . H241 . 1.000 no C24 . H242 . 1.000 no C24 . H243 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . C10 . 114.87(16) yes C8 . O2 . C9 . 113.01(14) yes O1 . C1 . C8 2_556 121.91(12) yes O1 . C1 . C2 . 116.96(12) yes C8 2_556 C1 . C2 . 121.12(13) yes C1 . C2 . C3 . 121.71(13) yes C1 . C2 . C7 . 117.90(12) yes C3 . C2 . C7 . 120.39(12) yes C2 . C3 . C4 . 120.64(13) yes C2 . C3 . H31 . 119.6 no C4 . C3 . H31 . 119.8 no C3 . C4 . C5 . 119.49(12) yes C3 . C4 . N1 . 119.50(13) yes C5 . C4 . N1 . 121.00(13) yes C4 . C5 . C6 . 120.68(13) yes C4 . C5 . H51 . 119.6 no C6 . C5 . H51 . 119.7 no C5 . C6 . C7 . 120.23(13) yes C5 . C6 . C8 . 122.10(12) yes C7 . C6 . C8 . 117.64(12) yes C6 . C7 . C7 2_556 120.47(15) yes C6 . C7 . C2 . 118.55(11) yes C7 2_556 C7 . C2 . 120.98(15) yes C6 . C8 . O2 . 117.03(12) yes C6 . C8 . C1 2_556 121.83(12) yes O2 . C8 . C1 2_556 121.12(13) yes O2 . C9 . H91 . 109.4 no O2 . C9 . H92 . 109.6 no H91 . C9 . H92 . 109.5 no O2 . C9 . H93 . 109.5 no H91 . C9 . H93 . 109.5 no H92 . C9 . H93 . 109.5 no O1 . C10 . H101 . 107.5 no O1 . C10 . H102 . 109.4 no H101 . C10 . H102 . 110.1 no O1 . C10 . H103 . 110.4 no H101 . C10 . H103 . 110.1 no H102 . C10 . H103 . 109.5 no C12 . C11 . C16 . 119.55(14) yes C12 . C11 . N1 . 119.57(14) yes C16 . C11 . N1 . 120.88(14) yes C11 . C12 . C13 . 119.83(14) yes C11 . C12 . H121 . 120.0 no C13 . C12 . H121 . 120.1 no C12 . C13 . C14 . 121.20(14) yes C12 . C13 . H131 . 119.5 no C14 . C13 . H131 . 119.3 no C13 . C14 . C15 . 118.19(14) yes C13 . C14 . C23 . 121.17(15) yes C15 . C14 . C23 . 120.64(15) yes C14 . C15 . C16 . 121.06(14) yes C14 . C15 . H151 . 119.3 no C16 . C15 . H151 . 119.6 no C11 . C16 . C15 . 120.16(14) yes C11 . C16 . H161 . 119.8 no C15 . C16 . H161 . 120.1 no C18 . C17 . C22 . 118.61(15) yes C18 . C17 . N1 . 120.82(15) yes C22 . C17 . N1 . 120.57(14) yes C17 . C18 . C19 . 120.62(18) yes C17 . C18 . H181 . 119.4 no C19 . C18 . H181 . 119.9 no C18 . C19 . C20 . 121.36(17) yes C18 . C19 . H191 . 119.5 no C20 . C19 . H191 . 119.1 no C19 . C20 . C21 . 117.34(16) yes C19 . C20 . C24 . 120.80(19) yes C21 . C20 . C24 . 121.9(2) yes C20 . C21 . C22 . 121.92(18) yes C20 . C21 . H211 . 118.6 no C22 . C21 . H211 . 119.4 no C21 . C22 . C17 . 120.15(17) yes C21 . C22 . H221 . 120.3 no C17 . C22 . H221 . 119.6 no C14 . C23 . H231 . 109.4 no C14 . C23 . H232 . 109.7 no H231 . C23 . H232 . 109.5 no C14 . C23 . H233 . 109.3 no H231 . C23 . H233 . 109.5 no H232 . C23 . H233 . 109.5 no C20 . C24 . H241 . 109.6 no C20 . C24 . H242 . 109.3 no H241 . C24 . H242 . 109.5 no C20 . C24 . H243 . 109.6 no H241 . C24 . H243 . 109.5 no H242 . C24 . H243 . 109.5 no C11 . N1 . C17 . 117.74(11) yes C11 . N1 . C4 . 119.92(12) yes C17 . N1 . C4 . 121.16(12) yes data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 857535' #TrackingRef '8578_web_deposit_cif_file_3_MartinBaumgarten_ #1323356323.pyr6ome_neu.cif' _audit_creation_date 11-10-06 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'pyrender.1 120K 09-09' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.1780(4) _cell_length_b 7.8530(2) _cell_length_c 14.2480(6) _cell_angle_alpha 90 _cell_angle_beta 97.6840(15) _cell_angle_gamma 90 _cell_volume 906.82(6) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C20 H22 O4 # Dc = 1.20 Fooo = 404.00 Mu = 0.82 M = 163.20 # Found Formula = C22 H22 O6 # Dc = 1.40 FOOO = 404.00 Mu = 1.02 M = 191.21 _chemical_formula_sum 'C22 H22 O6' _chemical_formula_moiety 'C22 H22 O6' _chemical_compound_source ? _chemical_formula_weight 382.41 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description prism _exptl_crystal_colour 'light yellow' _exptl_crystal_size_min 0.13 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.51 _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 404 _exptl_absorpt_coefficient_mu 0.102 # Sheldrick geometric approximatio 0.97 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 8692 _reflns_number_total 2875 _diffrn_reflns_av_R_equivalents 0.042 # Number of reflections with Friedels Law is 2875 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2884 _diffrn_reflns_theta_min 3.613 _diffrn_reflns_theta_max 30.972 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.972 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 20 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.21 _refine_diff_density_max 0.47 _refine_ls_number_reflns 2145 _refine_ls_number_restraints 0 _refine_ls_number_parameters 127 #_refine_ls_R_factor_ref 0.0414 _refine_ls_wR_factor_ref 0.0519 _refine_ls_goodness_of_fit_ref 1.0607 #_reflns_number_all 2871 _refine_ls_R_factor_all 0.0544 _refine_ls_wR_factor_all 0.0598 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 2145 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_gt 0.0519 _refine_ls_shift/su_max 0.000300 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.65 0.743 1.18 ; #_publ_section_title # Functionalization of Pyrene: from a Polycyclic #Aromatic Hydrocarbon to Electron- #Donors and Electron-Acceptors #; Chem. Eur. J. #; #_publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). #; #? #; #_publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. #; #? #; #_publ_section_acknowledgements # Acknowledgments #; #? #; #_publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line #; #Fig. 1. #The title compound with displacement ellipsoids drawn at the 50% #probability level. H atoms are shown as spheres of #arbitary radius. #; #_publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: #; #In the absence of significant anomalous scattering, Friedel pairs were #merged. #The absolute configuration was arbitrarily assigned. #The relatively large ratio of minimum to maximum corrections applied #in the multiscan process (1:nnn) reflect changes in the illuminated #volume of the crystal. #Changes in illuminated volume were kept to a minimum, and were #taken into account (G\"orbitz, 1999) by the multi-scan inter-frame #scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). #G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. #The H atoms were all located in a difference map, but those #attached to carbon atoms were repositioned geometrically. #The H atoms were initially refined with soft restraints on the #bond lengths and angles to regularise their geometry #(C---H in the range 0.93--0.98, #N---H in the range 0.86--0.89 #N---H to 0.86 #O---H = 0.82 #\%A) #and #U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), #after which the positions were refined with riding constraints. #; #_publ_section_exptl_prep # Brief details or a reference. Include solvent if known #; #? #; # PROCESSING SUMMARY (IUCr Office Use Only): #_journal_date_recd_electronic ? #_journal_date_to_coeditor ? #_journal_date_from_coeditor ? #_journal_date_accepted ? #_journal_date_printers_first ? #_journal_date_printers_final ? #_journal_date_proofs_out ? #_journal_date_proofs_in ? #_journal_coeditor_name ? #_journal_coeditor_code ? #_journal_coeditor_notes ? #_journal_techeditor_code ? #_journal_techeditor_notes ? #_journal_coden_ASTM ? #_journal_name_full ? #_journal_year ? #_journal_volume ? #_journal_issue ? #_journal_page_first ? #_journal_page_last ? #_journal_suppl_publ_number ? #_journal_suppl_publ_pages ? # # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C -0.08190(10) 0.49828(11) -0.02457(6) 0.0145 1.0000 Uani . . . . . . C2 C -0.12927(11) 0.37073(11) -0.09302(6) 0.0150 1.0000 Uani . . . . . . C3 C -0.28932(11) 0.36955(12) -0.14316(6) 0.0170 1.0000 Uani . . . . . . C4 C -0.40107(11) 0.49573(12) -0.12517(6) 0.0171 1.0000 Uani . . . . . . C5 C -0.35803(11) 0.62043(12) -0.05639(6) 0.0172 1.0000 Uani . . . . . . C6 C -0.19902(11) 0.62324(11) -0.00605(6) 0.0152 1.0000 Uani . . . . . . C7 C -0.14881(11) 0.75143(11) 0.06441(6) 0.0157 1.0000 Uani . . . . . . C8 C -0.00816(11) 0.24632(11) -0.11179(6) 0.0157 1.0000 Uani . . . . . . C9 C -0.03120(15) 0.16871(15) -0.27180(7) 0.0257 1.0000 Uani . . . . . . C10 C -0.60131(13) 0.39098(14) -0.24863(7) 0.0243 1.0000 Uani . . . . . . C11 C -0.24848(15) 1.02883(14) 0.03624(8) 0.0278 1.0000 Uani . . . . . . O1 O -0.05617(9) 0.12058(9) -0.17731(5) 0.0192 1.0000 Uani . . . . . . O2 O -0.55766(8) 0.50896(10) -0.17289(5) 0.0215 1.0000 Uani . . . . . . O3 O -0.26372(9) 0.86998(9) 0.08447(5) 0.0199 1.0000 Uani . . . . . . H31 H -0.3211 0.2835 -0.1889 0.0208 1.0000 Uiso R . . . . . H51 H -0.4368 0.7033 -0.0438 0.0212 1.0000 Uiso R . . . . . H91 H -0.0661 0.2892 -0.2813 0.0500 1.0000 Uiso R . . . . . H92 H 0.0873 0.1605 -0.2785 0.0500 1.0000 Uiso R . . . . . H93 H -0.0969 0.0909 -0.3158 0.0500 1.0000 Uiso R . . . . . H101 H -0.7050 0.4254 -0.2756 0.0500 1.0000 Uiso R . . . . . H102 H -0.5200 0.3950 -0.2935 0.0500 1.0000 Uiso R . . . . . H103 H -0.5975 0.2783 -0.2244 0.0500 1.0000 Uiso R . . . . . H111 H -0.3377 1.1017 0.0554 0.0500 1.0000 Uiso R . . . . . H112 H -0.1318 1.0734 0.0534 0.0500 1.0000 Uiso R . . . . . H113 H -0.2714 1.0071 -0.0301 0.0500 1.0000 Uiso 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 C1 0.0154(4) 0.0151(4) 0.0131(3) 0.0006(3) 0.0023(3) 0.0013(3) C2 0.0158(4) 0.0152(4) 0.0141(4) 0.0005(3) 0.0022(3) 0.0008(3) C3 0.0165(4) 0.0177(4) 0.0163(4) -0.0004(3) 0.0008(3) 0.0007(3) C4 0.0142(4) 0.0202(4) 0.0166(4) 0.0015(3) 0.0005(3) 0.0016(3) C5 0.0151(4) 0.0189(4) 0.0176(4) -0.0004(3) 0.0018(3) 0.0025(3) C6 0.0153(4) 0.0163(4) 0.0139(3) 0.0003(3) 0.0020(3) 0.0019(3) C7 0.0164(4) 0.0153(4) 0.0159(3) -0.0005(3) 0.0035(3) 0.0027(3) C8 0.0175(4) 0.0148(4) 0.0148(3) -0.0011(3) 0.0022(3) 0.0008(3) C9 0.0313(5) 0.0278(5) 0.0185(4) -0.0057(4) 0.0055(4) -0.0032(4) C10 0.0196(4) 0.0284(5) 0.0233(4) -0.0047(4) -0.0036(3) 0.0012(3) C11 0.0329(5) 0.0204(5) 0.0301(5) 0.0023(4) 0.0041(4) 0.0079(4) O1 0.0221(3) 0.0170(3) 0.0180(3) -0.0038(2) 0.0014(2) -0.0008(2) O2 0.0149(3) 0.0253(4) 0.0226(3) -0.0040(3) -0.0031(2) 0.0031(2) O3 0.0198(3) 0.0183(3) 0.0222(3) -0.0008(2) 0.0050(2) 0.0057(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 1.739(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C1 2_565 1.4264(17) yes C1 . C2 . 1.4155(12) yes C1 . C6 . 1.4204(12) yes C2 . C3 . 1.4049(12) yes C2 . C8 . 1.4415(12) yes C3 . C4 . 1.3948(13) yes C3 . H31 . 0.950 no C4 . C5 . 1.3968(13) yes C4 . O2 . 1.3711(11) yes C5 . C6 . 1.3988(12) yes C5 . H51 . 0.950 no C6 . C7 . 1.4421(12) yes C7 . C8 2_565 1.3683(12) yes C7 . O3 . 1.3796(10) yes C8 . O1 . 1.3793(11) yes C9 . O1 . 1.4389(13) yes C9 . H91 . 0.993 no C9 . H92 . 0.988 no C9 . H93 . 0.982 no C10 . O2 . 1.4309(12) yes C10 . H101 . 0.923 no C10 . H102 . 0.983 no C10 . H103 . 0.948 no C11 . O3 . 1.4376(13) yes C11 . H111 . 0.994 no C11 . H112 . 1.015 no C11 . H113 . 0.953 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 2_565 C1 . C2 . 120.27(10) yes C1 2_565 C1 . C6 . 120.54(10) yes C2 . C1 . C6 . 119.19(8) yes C1 . C2 . C3 . 120.37(8) yes C1 . C2 . C8 . 118.42(8) yes C3 . C2 . C8 . 121.18(8) yes C2 . C3 . C4 . 119.38(8) yes C2 . C3 . H31 . 120.3 no C4 . C3 . H31 . 120.3 no C3 . C4 . C5 . 121.14(8) yes C3 . C4 . O2 . 123.65(8) yes C5 . C4 . O2 . 115.20(8) yes C4 . C5 . C6 . 120.04(8) yes C4 . C5 . H51 . 120.0 no C6 . C5 . H51 . 120.0 no C1 . C6 . C5 . 119.84(8) yes C1 . C6 . C7 . 118.38(8) yes C5 . C6 . C7 . 121.78(8) yes C6 . C7 . C8 2_565 120.90(8) yes C6 . C7 . O3 . 118.48(8) yes C8 2_565 C7 . O3 . 120.61(8) yes C2 . C8 . C7 2_565 121.48(8) yes C2 . C8 . O1 . 118.06(8) yes C7 2_565 C8 . O1 . 120.43(8) yes O1 . C9 . H91 . 107.7 no O1 . C9 . H92 . 109.7 no H91 . C9 . H92 . 108.5 no O1 . C9 . H93 . 107.5 no H91 . C9 . H93 . 112.6 no H92 . C9 . H93 . 110.9 no O2 . C10 . H101 . 104.3 no O2 . C10 . H102 . 110.3 no H101 . C10 . H102 . 112.6 no O2 . C10 . H103 . 109.7 no H101 . C10 . H103 . 114.1 no H102 . C10 . H103 . 105.9 no O3 . C11 . H111 . 104.8 no O3 . C11 . H112 . 108.9 no H111 . C11 . H112 . 115.9 no O3 . C11 . H113 . 107.5 no H111 . C11 . H113 . 108.7 no H112 . C11 . H113 . 110.7 no C9 . O1 . C8 . 112.46(7) yes C10 . O2 . C4 . 116.56(8) yes C11 . O3 . C7 . 112.43(7) yes data_4Omepytcnq _database_code_depnum_ccdc_archive 'CCDC 857536' #TrackingRef '8579_web_deposit_cif_file_4_MartinBaumgarten_ #1323356323.4omepytcnq.cif' _audit_creation_date 10-08-10 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 14.2441(5) _cell_length_b 14.6744(7) _cell_length_c 13.2556(4) _cell_angle_alpha 90 _cell_angle_beta 115.853(2) _cell_angle_gamma 90 _cell_volume 2493.44(17) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C32 H22 N4 O4 # Dc = 1.40 Fooo = 1096.00 Mu = 0.95 M = 263.28 # Found Formula = C32 H22 N4 O4 # Dc = 1.40 FOOO = 1096.00 Mu = 0.95 M = 263.28 _chemical_formula_sum 'C32 H22 N4 O4' _chemical_formula_moiety 'C32 H22 N4 O4' _chemical_compound_source ? _chemical_formula_weight 526.55 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_max 0.43 _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 0.095 # Sheldrick geometric approximatio 0.97 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_absorpt_correction_T_min 0.66 _exptl_absorpt_correction_T_max 0.99 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 11259 _reflns_number_total 3640 _diffrn_reflns_av_R_equivalents 0.056 # Number of reflections with Friedels Law is 3640 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3641 _diffrn_reflns_theta_min 3.120 _diffrn_reflns_theta_max 30.021 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.021 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -20 _reflns_limit_h_max 18 _reflns_limit_k_min 0 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.45 _refine_diff_density_max 0.47 _refine_ls_number_reflns 2457 _refine_ls_number_restraints 0 _refine_ls_number_parameters 183 #_refine_ls_R_factor_ref 0.0485 _refine_ls_wR_factor_ref 0.0591 _refine_ls_goodness_of_fit_ref 1.0674 #_reflns_number_all 3633 _refine_ls_R_factor_all 0.0694 _refine_ls_wR_factor_all 0.0632 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.0\s(I) _reflns_number_gt 2457 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_gt 0.0591 _refine_ls_shift/su_max 0.000329 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.91 0.883 1.38 ; #_publ_section_title # Title of paper - generally just the systematic or trivial name #; ? #; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. #loop_ # _publ_author_name # _publ_author_address # _publ_author_footnote # 'Other, Anthony N.' # Author 1 #; # ? # Address for author 1 #; #; # ? # Footnote for author 1 #; # 'Else, S. O.' # Author 2 #; # ? # Address 2 #; #; # ? # Footnote 2 #; #_publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). #; #? #; #_publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. #; #? #; #_publ_section_acknowledgements # Acknowledgments #; #? #; #_publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line #; #Fig. 1. #The title compound with displacement ellipsoids drawn at the 50% #probability level. H atoms are shown as spheres of #arbitary radius. #; #_publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: #; #In the absence of significant anomalous scattering, Friedel pairs were #merged. #The absolute configuration was arbitrarily assigned. #The relatively large ratio of minimum to maximum corrections applied #in the multiscan process (1:nnn) reflect changes in the illuminated #volume of the crystal. #Changes in illuminated volume were kept to a minimum, and were #taken into account (G\"orbitz, 1999) by the multi-scan inter-frame #scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). #G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. #The H atoms were all located in a difference map, but those #attached to carbon atoms were repositioned geometrically. #The H atoms were initially refined with soft restraints on the #bond lengths and angles to regularise their geometry #(C---H in the range 0.93--0.98, #N---H in the range 0.86--0.89 #N---H to 0.86 #O---H = 0.82 #\%A) #and #U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), #after which the positions were refined with riding constraints. #; #_publ_section_exptl_prep # Brief details or a reference. Include solvent if known #; #? #; # PROCESSING SUMMARY (IUCr Office Use Only): #_journal_date_recd_electronic ? #_journal_date_to_coeditor ? #_journal_date_from_coeditor ? #_journal_date_accepted ? #_journal_date_printers_first ? #_journal_date_printers_final ? #_journal_date_proofs_out ? #_journal_date_proofs_in ? #_journal_coeditor_name ? #_journal_coeditor_code ? #_journal_coeditor_notes ? #_journal_techeditor_code ? #_journal_techeditor_notes ? #_journal_coden_ASTM ? #_journal_name_full ? #_journal_year ? #_journal_volume ? #_journal_issue ? #_journal_page_first ? #_journal_page_last ? #_journal_suppl_publ_number ? #_journal_suppl_publ_pages ? # # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.29447(8) 0.37732(7) -0.23365(8) 0.0229 1.0000 Uani . . . . . . O2 O 0.20630(9) 0.31580(8) 0.26077(8) 0.0254 1.0000 Uani . . . . . . C1 C 0.24883(10) 0.29814(9) 0.00651(10) 0.0171 1.0000 Uani . . . . . . C2 C 0.26203(10) 0.35701(9) -0.07121(11) 0.0180 1.0000 Uani . . . . . . C3 C 0.26083(11) 0.45187(10) -0.05714(11) 0.0211 1.0000 Uani . . . . . . C4 C 0.24641(11) 0.48731(10) 0.03274(12) 0.0227 1.0000 Uani . . . . . . C5 C 0.23395(11) 0.43051(10) 0.11000(11) 0.0213 1.0000 Uani . . . . . . C6 C 0.23510(10) 0.33538(9) 0.09823(10) 0.0176 1.0000 Uani . . . . . . C7 C 0.27839(10) 0.31788(10) -0.16201(11) 0.0193 1.0000 Uani . . . . . . C8 C 0.40264(12) 0.38471(12) -0.20975(14) 0.0294 1.0000 Uani . . . . . . C9 C 0.22231(10) 0.27428(10) 0.17661(10) 0.0189 1.0000 Uani . . . . . . C10 C 0.26112(13) 0.28083(12) 0.37266(12) 0.0291 1.0000 Uani . . . . . . C11 C 0.51023(13) 0.36331(11) 0.16354(13) 0.0292 1.0000 Uani . . . . . . C12 C 0.5000 0.31186(15) 0.2500 0.0236 1.0000 Uani S T . . . . C13 C 0.5000 0.21798(14) 0.2500 0.0204 1.0000 Uani S T . . . . C14 C 0.49716(11) 0.16788(11) 0.34220(11) 0.0214 1.0000 Uani . . . . . . C15 C 0.49882(11) 0.07577(10) 0.34302(11) 0.0210 1.0000 Uani . . . . . . C16 C 0.5000 0.02511(14) 0.2500 0.0194 1.0000 Uani S T . . . . C17 C 0.5000 -0.06890(14) 0.2500 0.0204 1.0000 Uani S T . . . . C18 C 0.48483(11) -0.12021(10) 0.15233(12) 0.0222 1.0000 Uani . . . . . . N11 N 0.52141(14) 0.40322(11) 0.09473(13) 0.0402 1.0000 Uani . . . . . . N12 N 0.46740(11) -0.16121(10) 0.07197(11) 0.0305 1.0000 Uani . . . . . . H31 H 0.2701 0.4917 -0.1086 0.0266 1.0000 Uiso R . . . . . H41 H 0.2450 0.5515 0.0413 0.0301 1.0000 Uiso R . . . . . H51 H 0.2243 0.4558 0.1708 0.0271 1.0000 Uiso R . . . . . H81 H 0.4101 0.4263 -0.2607 0.0384 1.0000 Uiso R . . . . . H82 H 0.4414 0.4060 -0.1352 0.0384 1.0000 Uiso R . . . . . H83 H 0.4280 0.3265 -0.2176 0.0384 1.0000 Uiso R . . . . . H101 H 0.2432 0.3154 0.4223 0.0378 1.0000 Uiso R . . . . . H102 H 0.3341 0.2850 0.3955 0.0378 1.0000 Uiso R . . . . . H103 H 0.2424 0.2189 0.3742 0.0378 1.0000 Uiso R . . . . . H141 H 0.4940 0.1999 0.4029 0.0270 1.0000 Uiso R . . . . . H151 H 0.4990 0.0437 0.4053 0.0267 1.0000 Uiso 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 0.0235(5) 0.0262(5) 0.0219(5) 0.0079(4) 0.0127(4) 0.0028(4) O2 0.0328(6) 0.0287(5) 0.0166(5) 0.0025(4) 0.0126(4) 0.0090(4) C1 0.0159(5) 0.0192(6) 0.0146(5) 0.0008(4) 0.0052(4) 0.0004(4) C2 0.0162(6) 0.0206(6) 0.0167(5) 0.0016(4) 0.0066(5) 0.0002(4) C3 0.0222(6) 0.0198(6) 0.0202(6) 0.0028(5) 0.0081(5) 0.0000(5) C4 0.0261(7) 0.0166(6) 0.0231(6) 0.0005(5) 0.0085(5) 0.0007(5) C5 0.0234(7) 0.0216(6) 0.0181(6) -0.0012(5) 0.0082(5) 0.0017(5) C6 0.0172(6) 0.0196(6) 0.0147(5) 0.0009(4) 0.0056(4) 0.0021(4) C7 0.0195(6) 0.0231(6) 0.0159(5) 0.0032(4) 0.0081(5) 0.0015(5) C8 0.0255(7) 0.0317(8) 0.0322(8) 0.0080(6) 0.0138(6) -0.0013(6) C9 0.0192(6) 0.0230(6) 0.0150(5) 0.0018(5) 0.0078(5) 0.0035(5) C10 0.0339(8) 0.0347(8) 0.0167(6) 0.0021(6) 0.0092(5) 0.0050(6) C11 0.0290(8) 0.0243(7) 0.0257(7) 0.0018(5) 0.0040(6) -0.0027(6) C12 0.0215(9) 0.0233(9) 0.0201(8) 0.0000 0.0037(7) 0.0000 C13 0.0158(8) 0.0245(9) 0.0180(8) 0.0000 0.0047(6) 0.0000 C14 0.0205(6) 0.0259(7) 0.0168(5) -0.0013(5) 0.0073(5) 0.0009(5) C15 0.0214(6) 0.0252(7) 0.0161(5) 0.0004(5) 0.0079(5) 0.0010(5) C16 0.0178(8) 0.0241(9) 0.0154(8) 0.0000 0.0065(6) 0.0000 C17 0.0189(9) 0.0248(9) 0.0156(8) 0.0000 0.0059(7) 0.0000 C18 0.0229(6) 0.0231(6) 0.0183(6) 0.0013(5) 0.0068(5) 0.0010(5) N11 0.0476(9) 0.0333(8) 0.0336(8) 0.0060(6) 0.0120(7) -0.0067(7) N12 0.0340(7) 0.0323(7) 0.0233(6) -0.0032(5) 0.0108(5) 0.0008(6) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C7 . 1.3801(16) yes O1 . C8 . 1.4354(18) yes O2 . C9 . 1.3746(16) yes O2 . C10 . 1.4363(17) yes C1 . C1 4_555 1.425(3) yes C1 . C2 . 1.4184(18) yes C1 . C6 . 1.4221(17) yes C2 . C3 . 1.4056(19) yes C2 . C7 . 1.4413(18) yes C3 . C4 . 1.395(2) yes C3 . H31 . 0.950 no C4 . C5 . 1.3906(19) yes C4 . H41 . 0.950 no C5 . C6 . 1.405(2) yes C5 . H51 . 0.950 no C6 . C9 . 1.4429(18) yes C7 . C9 4_555 1.366(2) yes C8 . H81 . 0.950 no C8 . H82 . 0.950 no C8 . H83 . 0.950 no C10 . H101 . 0.950 no C10 . H102 . 0.950 no C10 . H103 . 0.950 no C11 . C12 . 1.432(2) yes C11 . N11 . 1.152(2) yes C12 . C13 . 1.378(3) yes C13 . C14 5_655 1.4419(17) yes C13 . C14 . 1.4419(17) yes C14 . C15 . 1.352(2) yes C14 . H141 . 0.950 no C15 . C16 . 1.4462(17) yes C15 . H151 . 0.950 no C16 . C17 . 1.379(3) yes C17 . C18 5_655 1.4304(18) yes C17 . C18 . 1.4304(18) yes C18 . N12 . 1.152(2) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C7 . O1 . C8 . 112.34(11) yes C9 . O2 . C10 . 118.15(11) yes C1 4_555 C1 . C2 . 119.88(14) yes C1 4_555 C1 . C6 . 120.24(15) yes C2 . C1 . C6 . 119.87(12) yes C1 . C2 . C3 . 119.58(12) yes C1 . C2 . C7 . 119.00(12) yes C3 . C2 . C7 . 121.40(12) yes C2 . C3 . C4 . 119.83(12) yes C2 . C3 . H31 . 120.0 no C4 . C3 . H31 . 120.2 no C3 . C4 . C5 . 121.28(13) yes C3 . C4 . H41 . 119.4 no C5 . C4 . H41 . 119.3 no C4 . C5 . C6 . 120.14(12) yes C4 . C5 . H51 . 120.2 no C6 . C5 . H51 . 119.7 no C1 . C6 . C5 . 119.29(12) yes C1 . C6 . C9 . 118.97(12) yes C5 . C6 . C9 . 121.74(12) yes C2 . C7 . O1 . 117.30(12) yes C2 . C7 . C9 4_555 121.26(12) yes O1 . C7 . C9 4_555 121.43(12) yes O1 . C8 . H81 . 109.5 no O1 . C8 . H82 . 109.6 no H81 . C8 . H82 . 109.5 no O1 . C8 . H83 . 109.3 no H81 . C8 . H83 . 109.5 no H82 . C8 . H83 . 109.5 no C6 . C9 . O2 . 115.26(12) yes C6 . C9 . C7 4_555 120.58(12) yes O2 . C9 . C7 4_555 124.08(12) yes O2 . C10 . H101 . 109.6 no O2 . C10 . H102 . 109.4 no H101 . C10 . H102 . 109.5 no O2 . C10 . H103 . 109.4 no H101 . C10 . H103 . 109.5 no H102 . C10 . H103 . 109.5 no C12 . C11 . N11 . 177.79(18) yes C11 . C12 . C11 5_655 116.4(2) yes C11 . C12 . C13 . 121.82(10) yes C11 5_655 C12 . C13 . 121.82(10) yes C14 5_655 C13 . C12 . 120.66(9) yes C14 5_655 C13 . C14 . 118.68(19) yes C12 . C13 . C14 . 120.66(9) yes C13 . C14 . C15 . 120.65(14) yes C13 . C14 . H141 . 119.7 no C15 . C14 . H141 . 119.7 no C14 . C15 . C16 . 120.92(14) yes C14 . C15 . H151 . 119.7 no C16 . C15 . H151 . 119.3 no C15 . C16 . C15 5_655 118.13(18) yes C15 . C16 . C17 . 120.93(9) yes C15 5_655 C16 . C17 . 120.93(9) yes C18 5_655 C17 . C16 . 121.77(9) yes C18 5_655 C17 . C18 . 116.47(18) yes C16 . C17 . C18 . 121.77(9) yes C17 . C18 . N12 . 176.63(15) yes data_omepytcnq _database_code_depnum_ccdc_archive 'CCDC 857537' #TrackingRef '8580_web_deposit_cif_file_5_MartinBaumgarten_ #1323356323.publishHMPTCNQ.cif' _audit_creation_date 11-10-20 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 13.1831(7) _cell_length_b 12.9272(9) _cell_length_c 19.6341(9) _cell_angle_alpha 90 _cell_angle_beta 109.661(4) _cell_angle_gamma 90 _cell_volume 3151.0(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C34 H32 N4 O7 S1 # Dc = 1.35 Fooo = 1392.00 Mu = 1.59 M = 640.72 # Found Formula = C36 H32 N4 O7 S1 # Dc = 1.40 FOOO = 1392.00 Mu = 1.61 M = 664.74 _chemical_formula_sum 'C36 H32 N4 O7 S1' _chemical_formula_moiety 'C36 H32 N4 O7 S1' _chemical_compound_source ? _chemical_formula_weight 664.74 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_min 0.13 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_max 0.43 _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.161 # Sheldrick geometric approximatio 0.97 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 0.98 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS 86 (Sheldrick, 1986)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 23009 _reflns_number_total 7153 _diffrn_reflns_av_R_equivalents 0.056 # Number of reflections with Friedels Law is 7153 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 7200 _diffrn_reflns_theta_min 3.152 _diffrn_reflns_theta_max 27.449 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.077 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 25 _reflns_limit_h_min -17 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 25 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.32 _refine_diff_density_max 0.49 _refine_ls_number_reflns 5092 _refine_ls_number_restraints 0 _refine_ls_number_parameters 433 #_refine_ls_R_factor_ref 0.0316 _refine_ls_wR_factor_ref 0.0523 _refine_ls_goodness_of_fit_ref 0.9132 #_reflns_number_all 7153 _refine_ls_R_factor_all 0.0637 _refine_ls_wR_factor_all 0.1632 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5092 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_gt 0.0523 _refine_ls_shift/su_max 0.002993 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.698 0.784 0.262 ; # Insert your own references if required - in alphabetical order 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens S61 S -0.72351(2) 0.408547(19) 0.055042(14) 0.0382 1.0000 Uani . . . . . . O21 O -1.07480(6) 0.25841(5) -0.10915(4) 0.0337 1.0000 Uani . . . . . . O22 O -1.13209(5) -0.07314(5) -0.25941(3) 0.0299 1.0000 Uani . . . . . . O23 O -1.01575(5) -0.29642(5) -0.03890(3) 0.0277 1.0000 Uani . . . . . . O41 O -0.53953(6) 0.25059(5) -0.11540(4) 0.0351 1.0000 Uani . . . . . . O42 O -0.62578(6) -0.07800(5) -0.25670(3) 0.0325 1.0000 Uani . . . . . . O43 O -0.51810(5) -0.29839(4) -0.02975(3) 0.0269 1.0000 Uani . . . . . . O61 O -0.75909(6) 0.46232(6) -0.01722(4) 0.0474 1.0000 Uani . . . . . . N1 N -0.65049(7) 0.24547(6) 0.19635(4) 0.0329 1.0000 Uani . . . . . . N2 N -0.62684(7) -0.07771(6) 0.24860(4) 0.0340 1.0000 Uani . . . . . . N3 N -0.87295(6) 0.11258(7) -0.24599(4) 0.0356 1.0000 Uani . . . . . . N4 N -0.84614(7) -0.21715(7) -0.19633(4) 0.0371 1.0000 Uani . . . . . . C1 C -0.71294(6) 0.03567(7) 0.07540(5) 0.0255 1.0000 Uani . . . . . . C2 C -0.73966(6) 0.11651(7) 0.02129(5) 0.0262 1.0000 Uani . . . . . . C3 C -0.77578(6) 0.09458(7) -0.05020(5) 0.0266 1.0000 Uani . . . . . . C4 C -0.78752(6) -0.00875(7) -0.07394(5) 0.0262 1.0000 Uani . . . . . . C5 C -0.76221(6) -0.09223(7) -0.02315(5) 0.0275 1.0000 Uani . . . . . . C6 C -0.72639(6) -0.07125(7) 0.04862(5) 0.0269 1.0000 Uani . . . . . . C7 C -0.67831(7) 0.05805(7) 0.14729(5) 0.0266 1.0000 Uani . . . . . . C8 C -0.66377(7) 0.16211(7) 0.17378(5) 0.0289 1.0000 Uani . . . . . . C9 C -0.64869(7) -0.01737(7) 0.20426(5) 0.0296 1.0000 Uani . . . . . . C10 C -0.82545(6) -0.03074(8) -0.14871(5) 0.0287 1.0000 Uani . . . . . . C11 C -0.85208(7) 0.05085(8) -0.20173(5) 0.0309 1.0000 Uani . . . . . . C12 C -0.83784(7) -0.13244(8) -0.17425(5) 0.0319 1.0000 Uani . . . . . . C21 C -1.01995(5) -0.00890(6) -0.03710(4) 0.0164 1.0000 Uani . . . . . . C22 C -1.04793(6) 0.07426(6) -0.08820(4) 0.0196 1.0000 Uani . . . . . . C23 C -1.08704(7) 0.05514(7) -0.16247(4) 0.0241 1.0000 Uani . . . . . . C24 C -1.09573(6) -0.04530(7) -0.18656(4) 0.0235 1.0000 Uani . . . . . . C25 C -1.06973(6) -0.13118(6) -0.13831(4) 0.0202 1.0000 Uani . . . . . . C26 C -1.03205(6) -0.11401(6) -0.06518(4) 0.0179 1.0000 Uani . . . . . . C27 C -1.00162(6) -0.19772(6) -0.01251(4) 0.0216 1.0000 Uani . . . . . . C28 C -1.03679(7) 0.17726(6) -0.05935(4) 0.0231 1.0000 Uani . . . . . . C29 C -0.99564(8) 0.31360(9) -0.12646(6) 0.0455 1.0000 Uani . . . . . . C30 C -1.15507(8) 0.01254(7) -0.30987(5) 0.0305 1.0000 Uani . . . . . . C31 C -0.91671(9) -0.34512(9) -0.04171(7) 0.0502 1.0000 Uani . . . . . . C41 C -0.51754(5) -0.01219(5) -0.03787(4) 0.0160 1.0000 Uani . . . . . . C42 C -0.54117(6) 0.06839(6) -0.08926(4) 0.0198 1.0000 Uani . . . . . . C43 C -0.57652(7) 0.04190(6) -0.16341(5) 0.0256 1.0000 Uani . . . . . . C44 C -0.59077(7) -0.06187(7) -0.18640(5) 0.0243 1.0000 Uani . . . . . . C45 C -0.56691(6) -0.14046(6) -0.13455(4) 0.0198 1.0000 Uani . . . . . . C46 C -0.53056(6) -0.11464(6) -0.05992(4) 0.0170 1.0000 Uani . . . . . . C47 C -0.50828(6) -0.19505(6) -0.00644(4) 0.0207 1.0000 Uani . . . . . . C48 C -0.52429(7) 0.17433(6) -0.06425(5) 0.0235 1.0000 Uani . . . . . . C49 C -0.63112(9) 0.31264(10) -0.12814(6) 0.0461 1.0000 Uani . . . . . . C50 C -0.64161(8) -0.18454(9) -0.28380(6) 0.0413 1.0000 Uani . . . . . . C51 C -0.62241(10) -0.34492(9) -0.03776(7) 0.0500 1.0000 Uani . . . . . . C61 C -0.79993(10) 0.46377(9) 0.10634(7) 0.0481 1.0000 Uani . . . . . . C62 C -0.59488(9) 0.46064(10) 0.10620(6) 0.0479 1.0000 Uani . . . . . . H21 H -0.7321 0.1869 0.0360 0.0308 1.0000 Uiso R . . . . . H31 H -0.7929 0.1488 -0.0849 0.0264 1.0000 Uiso R . . . . . H51 H -0.7710 -0.1618 -0.0397 0.0352 1.0000 Uiso R . . . . . H61 H -0.7090 -0.1264 0.0826 0.0295 1.0000 Uiso R . . . . . H231 H -1.1079 0.1106 -0.1960 0.0277 1.0000 Uiso R . . . . . H251 H -1.0785 -0.1998 -0.1568 0.0247 1.0000 Uiso R . . . . . H291 H -1.0281 0.3667 -0.1602 0.0569 1.0000 Uiso R . . . . . H292 H -0.9477 0.3436 -0.0835 0.0569 1.0000 Uiso R . . . . . H293 H -0.9569 0.2682 -0.1468 0.0569 1.0000 Uiso R . . . . . H301 H -1.1797 -0.0133 -0.3580 0.0417 1.0000 Uiso R . . . . . H302 H -1.2092 0.0550 -0.3024 0.0417 1.0000 Uiso R . . . . . H303 H -1.0915 0.0522 -0.3023 0.0417 1.0000 Uiso R . . . . . H311 H -0.9326 -0.4132 -0.0606 0.0631 1.0000 Uiso R . . . . . H312 H -0.8643 -0.3482 0.0053 0.0631 1.0000 Uiso R . . . . . H313 H -0.8895 -0.3054 -0.0724 0.0631 1.0000 Uiso R . . . . . H431 H -0.5904 0.0953 -0.1986 0.0290 1.0000 Uiso R . . . . . H451 H -0.5750 -0.2109 -0.1492 0.0305 1.0000 Uiso R . . . . . H491 H -0.6330 0.3636 -0.1634 0.0566 1.0000 Uiso R . . . . . H492 H -0.6931 0.2698 -0.1455 0.0566 1.0000 Uiso R . . . . . H493 H -0.6302 0.3456 -0.0847 0.0566 1.0000 Uiso R . . . . . H501 H -0.6663 -0.1840 -0.3352 0.0542 1.0000 Uiso R . . . . . H502 H -0.6934 -0.2180 -0.2675 0.0542 1.0000 Uiso R . . . . . H503 H -0.5751 -0.2207 -0.2663 0.0542 1.0000 Uiso R . . . . . H511 H -0.6235 -0.4145 -0.0535 0.0625 1.0000 Uiso R . . . . . H512 H -0.6347 -0.3435 0.0072 0.0625 1.0000 Uiso R . . . . . H513 H -0.6773 -0.3067 -0.0726 0.0625 1.0000 Uiso R . . . . . H611 H -0.8769 0.4421 0.0846 0.0542 1.0000 Uiso R . . . . . H612 H -0.7952 0.5409 0.1057 0.0542 1.0000 Uiso R . . . . . H613 H -0.7704 0.4385 0.1574 0.0542 1.0000 Uiso R . . . . . H621 H -0.5400 0.4376 0.0845 0.0567 1.0000 Uiso R . . . . . H622 H -0.5987 0.5379 0.1056 0.0567 1.0000 Uiso R . . . . . H623 H -0.5739 0.4354 0.1572 0.0567 1.0000 Uiso 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 S61 0.04617(14) 0.02839(12) 0.03729(14) -0.00357(9) 0.01023(11) -0.00187(10) O21 0.0488(4) 0.0220(3) 0.0280(3) 0.0067(2) 0.0100(3) 0.0090(3) O22 0.0315(3) 0.0354(3) 0.0195(3) -0.0024(3) 0.0043(2) -0.0018(3) O23 0.0365(3) 0.0183(3) 0.0306(3) -0.0013(2) 0.0142(3) 0.0002(2) O41 0.0607(4) 0.0167(3) 0.0345(3) 0.0064(3) 0.0245(3) 0.0067(3) O42 0.0394(4) 0.0312(3) 0.0254(3) -0.0032(3) 0.0092(3) 0.0051(3) O43 0.0373(3) 0.0136(3) 0.0374(3) -0.0014(2) 0.0227(3) -0.0017(2) O61 0.0437(4) 0.0428(4) 0.0528(5) 0.0150(4) 0.0123(3) 0.0041(3) N1 0.0383(4) 0.0328(4) 0.0291(4) 0.0000(3) 0.0134(3) -0.0053(3) N2 0.0347(4) 0.0337(4) 0.0292(4) 0.0020(3) 0.0052(3) -0.0027(3) N3 0.0317(4) 0.0502(5) 0.0279(4) 0.0021(4) 0.0140(3) 0.0055(4) N4 0.0332(4) 0.0468(5) 0.0329(4) -0.0076(4) 0.0134(3) 0.0013(4) C1 0.0167(4) 0.0327(4) 0.0279(4) 0.0002(3) 0.0087(3) 0.0007(3) C2 0.0191(4) 0.0344(4) 0.0275(4) 0.0010(3) 0.0111(3) 0.0023(3) C3 0.0179(4) 0.0368(5) 0.0281(4) 0.0011(3) 0.0115(3) 0.0035(3) C4 0.0150(3) 0.0382(5) 0.0277(4) -0.0008(4) 0.0100(3) 0.0033(3) C5 0.0184(4) 0.0356(5) 0.0297(4) -0.0017(4) 0.0096(3) 0.0025(3) C6 0.0181(4) 0.0339(5) 0.0290(4) -0.0004(4) 0.0082(3) 0.0021(3) C7 0.0203(4) 0.0324(4) 0.0273(4) 0.0006(3) 0.0082(3) -0.0013(3) C8 0.0272(4) 0.0325(5) 0.0280(4) 0.0015(4) 0.0105(3) -0.0030(3) C9 0.0253(4) 0.0333(5) 0.0283(4) 0.0011(4) 0.0064(3) -0.0024(3) C10 0.0176(4) 0.0425(5) 0.0285(4) -0.0018(4) 0.0112(3) 0.0038(3) C11 0.0225(4) 0.0451(5) 0.0278(4) -0.0005(4) 0.0122(3) 0.0043(4) C12 0.0233(4) 0.0446(5) 0.0299(4) -0.0043(4) 0.0117(3) 0.0023(4) C21 0.0108(3) 0.0180(3) 0.0195(4) 0.0011(3) 0.0039(3) 0.0024(3) C22 0.0177(3) 0.0196(4) 0.0201(4) 0.0021(3) 0.0042(3) 0.0033(3) C23 0.0249(4) 0.0254(4) 0.0190(4) 0.0027(3) 0.0035(3) 0.0037(3) C24 0.0214(4) 0.0278(4) 0.0191(4) -0.0005(3) 0.0039(3) 0.0004(3) C25 0.0165(3) 0.0231(4) 0.0207(4) -0.0025(3) 0.0058(3) -0.0012(3) C26 0.0138(3) 0.0190(3) 0.0203(4) -0.0002(3) 0.0052(3) 0.0011(3) C27 0.0230(4) 0.0180(4) 0.0240(4) 0.0006(3) 0.0081(3) 0.0020(3) C28 0.0263(4) 0.0189(4) 0.0232(4) 0.0031(3) 0.0070(3) 0.0047(3) C29 0.0357(5) 0.0395(6) 0.0515(6) -0.0008(5) 0.0019(5) 0.0030(4) C30 0.0397(5) 0.0225(4) 0.0274(4) 0.0030(3) 0.0089(4) 0.0004(3) C31 0.0397(6) 0.0365(6) 0.0777(8) -0.0128(5) 0.0241(5) 0.0003(4) C41 0.0120(3) 0.0136(3) 0.0250(4) 0.0008(3) 0.0097(3) 0.0008(2) C42 0.0213(4) 0.0154(3) 0.0255(4) 0.0018(3) 0.0116(3) 0.0025(3) C43 0.0321(4) 0.0211(4) 0.0249(4) 0.0022(3) 0.0114(3) 0.0054(3) C44 0.0254(4) 0.0231(4) 0.0253(4) -0.0020(3) 0.0097(3) 0.0027(3) C45 0.0172(3) 0.0183(3) 0.0266(4) -0.0032(3) 0.0109(3) -0.0012(3) C46 0.0138(3) 0.0143(3) 0.0262(4) -0.0006(3) 0.0111(3) -0.0007(2) C47 0.0238(4) 0.0134(3) 0.0299(4) 0.0002(3) 0.0155(3) -0.0005(3) C48 0.0319(4) 0.0142(3) 0.0289(4) 0.0029(3) 0.0160(3) 0.0031(3) C49 0.0511(6) 0.0538(7) 0.0356(5) 0.0032(5) 0.0177(5) -0.0020(5) C50 0.0349(5) 0.0528(6) 0.0316(5) -0.0035(4) 0.0050(4) 0.0077(4) C51 0.0537(6) 0.0412(6) 0.0628(7) -0.0116(5) 0.0298(6) -0.0115(5) C61 0.0524(6) 0.0501(6) 0.0524(6) -0.0162(5) 0.0315(5) -0.0125(5) C62 0.0431(6) 0.0571(7) 0.0389(6) -0.0074(5) 0.0078(4) 0.0095(5) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S61 . O61 . 1.5062(8) yes S61 . C61 . 1.7949(11) yes S61 . C62 . 1.7866(12) yes O21 . C28 . 1.4066(10) yes O21 . C29 . 1.3972(14) yes O22 . C24 . 1.3942(10) yes O22 . C30 . 1.4486(10) yes O23 . C27 . 1.3660(10) yes O23 . C31 . 1.4672(12) yes O41 . C48 . 1.3730(10) yes O41 . C49 . 1.4002(13) yes O42 . C44 . 1.3165(10) yes O42 . C50 . 1.4658(12) yes O43 . C47 . 1.4040(9) yes O43 . C51 . 1.4601(12) yes N1 . C8 . 1.1559(12) yes N2 . C9 . 1.1317(12) yes N3 . C11 . 1.1432(13) yes N4 . C12 . 1.1693(14) yes C1 . C2 . 1.4468(13) yes C1 . C6 . 1.4683(12) yes C1 . C7 . 1.3604(12) yes C2 . C3 . 1.3518(12) yes C2 . H21 . 0.950 no C3 . C4 . 1.4060(13) yes C3 . H31 . 0.950 no C4 . C5 . 1.4306(13) yes C4 . C10 . 1.4113(12) yes C5 . C6 . 1.3543(12) yes C5 . H51 . 0.950 no C6 . H61 . 0.950 no C7 . C8 . 1.4317(13) yes C7 . C9 . 1.4353(13) yes C10 . C11 . 1.4400(14) yes C10 . C12 . 1.3969(14) yes C21 . C21 2_355 1.3915(14) yes C21 . C22 . 1.4315(10) yes C21 . C26 . 1.4549(10) yes C22 . C23 . 1.3955(11) yes C22 . C28 . 1.4350(11) yes C23 . C24 . 1.3734(12) yes C23 . H231 . 0.950 no C24 . C25 . 1.4244(11) yes C25 . C26 . 1.3702(10) yes C25 . H251 . 0.950 no C26 . C27 . 1.4568(11) yes C27 . C28 2_355 1.3551(11) yes C29 . H291 . 0.950 no C29 . H292 . 0.950 no C29 . H293 . 0.950 no C30 . H301 . 0.950 no C30 . H302 . 0.950 no C30 . H303 . 0.950 no C31 . H311 . 0.950 no C31 . H312 . 0.950 no C31 . H313 . 0.950 no C41 . C41 2_455 1.4361(15) yes C41 . C42 . 1.4101(10) yes C41 . C46 . 1.3859(10) yes C42 . C43 . 1.4134(12) yes C42 . C48 . 1.4466(11) yes C43 . C44 . 1.4076(11) yes C43 . H431 . 0.950 no C44 . C45 . 1.3971(11) yes C45 . C46 . 1.4198(11) yes C45 . H451 . 0.950 no C46 . C47 . 1.4359(11) yes C47 . C48 2_455 1.3348(12) yes C49 . H491 . 0.950 no C49 . H492 . 0.950 no C49 . H493 . 0.950 no C50 . H501 . 0.950 no C50 . H502 . 0.950 no C50 . H503 . 0.950 no C51 . H511 . 0.950 no C51 . H512 . 0.950 no C51 . H513 . 0.950 no C61 . H611 . 1.000 no C61 . H612 . 1.000 no C61 . H613 . 1.000 no C62 . H621 . 1.000 no C62 . H622 . 1.000 no C62 . H623 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O61 . S61 . C61 . 106.82(6) yes O61 . S61 . C62 . 106.95(5) yes C61 . S61 . C62 . 98.07(5) yes C28 . O21 . C29 . 115.43(7) yes C24 . O22 . C30 . 115.14(7) yes C27 . O23 . C31 . 113.93(7) yes C48 . O41 . C49 . 116.56(7) yes C44 . O42 . C50 . 119.09(7) yes C47 . O43 . C51 . 114.03(7) yes C2 . C1 . C6 . 116.53(8) yes C2 . C1 . C7 . 121.48(8) yes C6 . C1 . C7 . 121.99(8) yes C1 . C2 . C3 . 121.65(9) yes C1 . C2 . H21 . 119.6 no C3 . C2 . H21 . 118.8 no C2 . C3 . C4 . 120.30(9) yes C2 . C3 . H31 . 120.3 no C4 . C3 . H31 . 119.4 no C3 . C4 . C5 . 120.78(8) yes C3 . C4 . C10 . 119.81(8) yes C5 . C4 . C10 . 119.41(9) yes C4 . C5 . C6 . 119.48(9) yes C4 . C5 . H51 . 120.2 no C6 . C5 . H51 . 120.3 no C1 . C6 . C5 . 121.27(8) yes C1 . C6 . H61 . 118.9 no C5 . C6 . H61 . 119.8 no C1 . C7 . C8 . 122.27(8) yes C1 . C7 . C9 . 124.92(9) yes C8 . C7 . C9 . 112.77(8) yes C7 . C8 . N1 . 178.68(10) yes C7 . C9 . N2 . 178.86(9) yes C4 . C10 . C11 . 121.28(9) yes C4 . C10 . C12 . 121.38(9) yes C11 . C10 . C12 . 117.33(8) yes C10 . C11 . N3 . 177.04(10) yes C10 . C12 . N4 . 178.29(10) yes C21 2_355 C21 . C22 . 121.81(9) yes C21 2_355 C21 . C26 . 120.39(8) yes C22 . C21 . C26 . 117.79(7) yes C21 . C22 . C23 . 121.12(7) yes C21 . C22 . C28 . 116.88(7) yes C23 . C22 . C28 . 121.98(7) yes C22 . C23 . C24 . 119.08(8) yes C22 . C23 . H231 . 120.7 no C24 . C23 . H231 . 120.3 no O22 . C24 . C23 . 123.88(7) yes O22 . C24 . C25 . 113.82(7) yes C23 . C24 . C25 . 122.29(7) yes C24 . C25 . C26 . 119.47(7) yes C24 . C25 . H251 . 120.2 no C26 . C25 . H251 . 120.4 no C21 . C26 . C25 . 120.22(7) yes C21 . C26 . C27 . 117.12(7) yes C25 . C26 . C27 . 122.66(7) yes C26 . C27 . O23 . 117.05(7) yes C26 . C27 . C28 2_355 120.74(7) yes O23 . C27 . C28 2_355 122.19(7) yes C22 . C28 . O21 . 116.90(7) yes C22 . C28 . C27 2_355 123.02(7) yes O21 . C28 . C27 2_355 119.94(7) yes O21 . C29 . H291 . 109.9 no O21 . C29 . H292 . 108.7 no H291 . C29 . H292 . 109.5 no O21 . C29 . H293 . 109.7 no H291 . C29 . H293 . 109.5 no H292 . C29 . H293 . 109.5 no O22 . C30 . H301 . 109.5 no O22 . C30 . H302 . 109.3 no H301 . C30 . H302 . 109.5 no O22 . C30 . H303 . 109.6 no H301 . C30 . H303 . 109.5 no H302 . C30 . H303 . 109.5 no O23 . C31 . H311 . 109.3 no O23 . C31 . H312 . 110.3 no H311 . C31 . H312 . 109.5 no O23 . C31 . H313 . 108.9 no H311 . C31 . H313 . 109.5 no H312 . C31 . H313 . 109.5 no C41 2_455 C41 . C42 . 119.70(8) yes C41 2_455 C41 . C46 . 119.74(8) yes C42 . C41 . C46 . 120.54(7) yes C41 . C42 . C43 . 118.35(7) yes C41 . C42 . C48 . 119.00(7) yes C43 . C42 . C48 . 122.60(7) yes C42 . C43 . C44 . 121.56(8) yes C42 . C43 . H431 . 119.2 no C44 . C43 . H431 . 119.2 no C43 . C44 . O42 . 116.68(8) yes C43 . C44 . C45 . 119.10(8) yes O42 . C44 . C45 . 124.22(8) yes C44 . C45 . C46 . 119.74(7) yes C44 . C45 . H451 . 120.1 no C46 . C45 . H451 . 120.2 no C45 . C46 . C41 . 120.68(7) yes C45 . C46 . C47 . 119.97(7) yes C41 . C46 . C47 . 119.34(7) yes C46 . C47 . O43 . 118.47(7) yes C46 . C47 . C48 2_455 122.02(7) yes O43 . C47 . C48 2_455 119.48(7) yes C42 . C48 . O41 . 117.62(7) yes C42 . C48 . C47 2_455 120.12(7) yes O41 . C48 . C47 2_455 122.22(7) yes O41 . C49 . H491 . 109.7 no O41 . C49 . H492 . 108.4 no H491 . C49 . H492 . 109.5 no O41 . C49 . H493 . 110.3 no H491 . C49 . H493 . 109.5 no H492 . C49 . H493 . 109.5 no O42 . C50 . H501 . 109.5 no O42 . C50 . H502 . 109.6 no H501 . C50 . H502 . 109.5 no O42 . C50 . H503 . 109.3 no H501 . C50 . H503 . 109.5 no H502 . C50 . H503 . 109.5 no O43 . C51 . H511 . 109.6 no O43 . C51 . H512 . 109.9 no H511 . C51 . H512 . 109.5 no O43 . C51 . H513 . 108.9 no H511 . C51 . H513 . 109.5 no H512 . C51 . H513 . 109.5 no S61 . C61 . H611 . 109.3 no S61 . C61 . H612 . 109.9 no H611 . C61 . H612 . 109.5 no S61 . C61 . H613 . 109.2 no H611 . C61 . H613 . 109.5 no H612 . C61 . H613 . 109.5 no S61 . C62 . H621 . 109.5 no S61 . C62 . H622 . 109.6 no H621 . C62 . H622 . 109.5 no S61 . C62 . H623 . 109.3 no H621 . C62 . H623 . 109.5 no H622 . C62 . H623 . 109.5 no