# Electronic Supplementary Material (ESI) for Polymer Chemistry # 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_fs88cub _database_code_depnum_ccdc_archive 'CCDC 918310' #TrackingRef '16645_web_deposit_cif_file_0_FlorianSchluetter_1357558163.fs080cub.cif' _audit_creation_date 12-01-11 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.9080(2) _cell_length_b 10.7787(3) _cell_length_c 12.7321(3) _cell_angle_alpha 97.6691(12) _cell_angle_beta 94.7545(14) _cell_angle_gamma 115.8972(11) _cell_volume 1196.95(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' _cell_formula_units_Z 2 # Given Formula = C36 H26 # Dc = 1.27 Fooo = 484.00 Mu = 0.72 M = 458.60 # Found Formula = C36 H26 # Dc = 1.27 FOOO = 484.00 Mu = 0.72 M = 458.60 _chemical_formula_sum 'C36 H26' _chemical_formula_moiety 'C36 H26' _chemical_compound_source ? _chemical_formula_weight 458.60 _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 0.14 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_max 0.42 _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 0.072 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_absorpt_correction_T_min 0.95 _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 17782 _reflns_number_total 7607 _diffrn_reflns_av_R_equivalents 0.072 # Number of reflections with Friedels Law is 7607 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 7666 _diffrn_reflns_theta_min 1.634 _diffrn_reflns_theta_max 31.051 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 29.188 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -14 _reflns_limit_h_max 14 _reflns_limit_k_min -15 _reflns_limit_k_max 15 _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 -0.24 _refine_diff_density_max 0.39 _refine_ls_number_reflns 5798 _refine_ls_number_restraints 0 _refine_ls_number_parameters 325 #_refine_ls_R_factor_ref 0.0482 _refine_ls_wR_factor_ref 0.0590 _refine_ls_goodness_of_fit_ref 1.0869 #_reflns_number_all 7588 _refine_ls_R_factor_all 0.0645 _refine_ls_wR_factor_all 0.0806 # 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 5798 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_gt 0.0590 _refine_ls_shift/su_max 0.004695 # 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: 2.04 0.842 1.42 ; # 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 0.57363(11) 0.79644(11) 0.82286(8) 0.0168 1.0000 Uani . . . . . . C2 C 0.60460(12) 0.89645(11) 0.91608(8) 0.0197 1.0000 Uani . . . . . . C3 C 0.56749(13) 0.85517(13) 1.01303(8) 0.0224 1.0000 Uani . . . . . . C4 C 0.49878(13) 0.71350(13) 1.01952(9) 0.0235 1.0000 Uani . . . . . . C5 C 0.46633(14) 0.61334(12) 0.92748(9) 0.0235 1.0000 Uani . . . . . . C6 C 0.50436(12) 0.65402(11) 0.83049(8) 0.0203 1.0000 Uani . . . . . . C7 C 0.61278(11) 0.83996(11) 0.71921(8) 0.0163 1.0000 Uani . . . . . . C8 C 0.52598(11) 0.75565(11) 0.62099(8) 0.0168 1.0000 Uani . . . . . . C9 C 0.55869(11) 0.79689(11) 0.52232(8) 0.0163 1.0000 Uani . . . . . . C10 C 0.68559(11) 0.92552(11) 0.52208(8) 0.0170 1.0000 Uani . . . . . . C11 C 0.77032(12) 1.01096(11) 0.62021(8) 0.0186 1.0000 Uani . . . . . . C12 C 0.73529(12) 0.96935(11) 0.71709(8) 0.0179 1.0000 Uani . . . . . . C13 C 0.73693(12) 0.97799(11) 0.42257(8) 0.0171 1.0000 Uani . . . . . . C14 C 0.80185(11) 0.91760(10) 0.35062(8) 0.0156 1.0000 Uani . . . . . . C15 C 0.85288(11) 0.98090(10) 0.26263(8) 0.0165 1.0000 Uani . . . . . . C16 C 0.84037(11) 1.10033(10) 0.24279(8) 0.0161 1.0000 Uani . . . . . . C17 C 0.77367(12) 1.15753(11) 0.31471(8) 0.0195 1.0000 Uani . . . . . . C18 C 0.72558(13) 1.09804(12) 0.40324(8) 0.0205 1.0000 Uani . . . . . . C19 C 0.89728(11) 1.16603(10) 0.14993(8) 0.0160 1.0000 Uani . . . . . . C20 C 1.02032(12) 1.15811(11) 0.10832(8) 0.0194 1.0000 Uani . . . . . . C21 C 1.07316(13) 1.22002(12) 0.02102(9) 0.0236 1.0000 Uani . . . . . . C22 C 1.00426(14) 1.29180(12) -0.02582(9) 0.0234 1.0000 Uani . . . . . . C23 C 0.88241(13) 1.30148(11) 0.01518(9) 0.0212 1.0000 Uani . . . . . . C24 C 0.82857(12) 1.23835(11) 0.10178(8) 0.0184 1.0000 Uani . . . . . . C25 C 0.45079(11) 0.70879(11) 0.42239(8) 0.0176 1.0000 Uani . . . . . . C26 C 0.40168(13) 0.77073(12) 0.34801(8) 0.0212 1.0000 Uani . . . . . . C27 C 0.29241(14) 0.68872(13) 0.25896(9) 0.0257 1.0000 Uani . . . . . . C28 C 0.23149(14) 0.54322(14) 0.24105(9) 0.0266 1.0000 Uani . . . . . . C29 C 0.27932(14) 0.48047(13) 0.31427(10) 0.0263 1.0000 Uani . . . . . . C30 C 0.38635(13) 0.56207(12) 0.40437(9) 0.0227 1.0000 Uani . . . . . . C31 C 0.82571(11) 0.79322(10) 0.36503(8) 0.0167 1.0000 Uani . . . . . . C32 C 0.87653(12) 0.77664(11) 0.46590(9) 0.0201 1.0000 Uani . . . . . . C33 C 0.91171(13) 0.66654(12) 0.47563(10) 0.0241 1.0000 Uani . . . . . . C34 C 0.89946(14) 0.57194(12) 0.38544(11) 0.0268 1.0000 Uani . . . . . . C35 C 0.84772(14) 0.58613(12) 0.28489(10) 0.0258 1.0000 Uani . . . . . . C36 C 0.80969(13) 0.69464(11) 0.27510(9) 0.0210 1.0000 Uani . . . . . . H21 H 0.6514 0.9935 0.9127 0.0260 1.0000 Uiso R . . . . . H31 H 0.5895 0.9243 1.0753 0.0292 1.0000 Uiso R . . . . . H41 H 0.4742 0.6855 1.0859 0.0307 1.0000 Uiso R . . . . . H51 H 0.4176 0.5164 0.9309 0.0307 1.0000 Uiso R . . . . . H61 H 0.4835 0.5847 0.7686 0.0271 1.0000 Uiso R . . . . . H81 H 0.4422 0.6676 0.6212 0.0225 1.0000 Uiso R . . . . . H111 H 0.8538 1.0994 0.6204 0.0249 1.0000 Uiso R . . . . . H121 H 0.7949 1.0293 0.7826 0.0236 1.0000 Uiso R . . . . . H151 H 0.8977 0.9408 0.2144 0.0219 1.0000 Uiso R . . . . . H171 H 0.7611 1.2372 0.3026 0.0260 1.0000 Uiso R . . . . . H181 H 0.6836 1.1400 0.4524 0.0272 1.0000 Uiso R . . . . . H201 H 1.0683 1.1098 0.1403 0.0262 1.0000 Uiso R . . . . . H211 H 1.1564 1.2131 -0.0064 0.0310 1.0000 Uiso R . . . . . H221 H 1.0400 1.3337 -0.0855 0.0303 1.0000 Uiso R . . . . . H231 H 0.8359 1.3515 -0.0159 0.0278 1.0000 Uiso R . . . . . H241 H 0.7443 1.2439 0.1285 0.0249 1.0000 Uiso R . . . . . H261 H 0.4439 0.8702 0.3585 0.0285 1.0000 Uiso R . . . . . H271 H 0.2587 0.7324 0.2100 0.0338 1.0000 Uiso R . . . . . H281 H 0.1585 0.4873 0.1793 0.0346 1.0000 Uiso R . . . . . H291 H 0.2386 0.3811 0.3029 0.0350 1.0000 Uiso R . . . . . H301 H 0.4163 0.5178 0.4548 0.0306 1.0000 Uiso R . . . . . H321 H 0.8875 0.8416 0.5282 0.0263 1.0000 Uiso R . . . . . H331 H 0.9440 0.6558 0.5447 0.0315 1.0000 Uiso R . . . . . H341 H 0.9260 0.4984 0.3924 0.0347 1.0000 Uiso R . . . . . H351 H 0.8388 0.5219 0.2227 0.0340 1.0000 Uiso R . . . . . H361 H 0.7724 0.7021 0.2063 0.0281 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 0.0157(4) 0.0210(4) 0.0126(4) 0.0029(3) 0.0014(3) 0.0076(3) C2 0.0199(4) 0.0212(5) 0.0150(4) 0.0017(3) 0.0021(3) 0.0072(4) C3 0.0220(5) 0.0292(5) 0.0135(4) 0.0011(4) 0.0013(3) 0.0103(4) C4 0.0230(5) 0.0321(6) 0.0157(4) 0.0069(4) 0.0040(4) 0.0120(4) C5 0.0270(5) 0.0239(5) 0.0186(5) 0.0069(4) 0.0038(4) 0.0098(4) C6 0.0220(5) 0.0214(5) 0.0159(4) 0.0033(3) 0.0023(4) 0.0085(4) C7 0.0158(4) 0.0198(4) 0.0132(4) 0.0030(3) 0.0018(3) 0.0079(3) C8 0.0161(4) 0.0195(4) 0.0134(4) 0.0029(3) 0.0019(3) 0.0070(3) C9 0.0154(4) 0.0205(4) 0.0130(4) 0.0029(3) 0.0021(3) 0.0084(3) C10 0.0167(4) 0.0210(4) 0.0136(4) 0.0040(3) 0.0040(3) 0.0084(4) C11 0.0168(4) 0.0201(4) 0.0159(4) 0.0032(3) 0.0031(3) 0.0057(4) C12 0.0170(4) 0.0201(4) 0.0135(4) 0.0020(3) 0.0018(3) 0.0062(4) C13 0.0166(4) 0.0201(4) 0.0136(4) 0.0035(3) 0.0034(3) 0.0070(3) C14 0.0150(4) 0.0166(4) 0.0134(4) 0.0027(3) 0.0010(3) 0.0058(3) C15 0.0167(4) 0.0176(4) 0.0142(4) 0.0027(3) 0.0029(3) 0.0070(3) C16 0.0152(4) 0.0173(4) 0.0135(4) 0.0025(3) 0.0015(3) 0.0056(3) C17 0.0232(5) 0.0207(4) 0.0171(4) 0.0047(4) 0.0054(4) 0.0115(4) C18 0.0242(5) 0.0230(5) 0.0181(4) 0.0051(4) 0.0074(4) 0.0131(4) C19 0.0164(4) 0.0154(4) 0.0125(4) 0.0018(3) 0.0011(3) 0.0041(3) C20 0.0201(4) 0.0215(5) 0.0177(4) 0.0052(4) 0.0046(3) 0.0096(4) C21 0.0241(5) 0.0271(5) 0.0209(5) 0.0070(4) 0.0086(4) 0.0112(4) C22 0.0267(5) 0.0248(5) 0.0163(4) 0.0064(4) 0.0049(4) 0.0084(4) C23 0.0242(5) 0.0210(5) 0.0167(4) 0.0054(4) 0.0012(4) 0.0087(4) C24 0.0178(4) 0.0193(4) 0.0162(4) 0.0033(3) 0.0010(3) 0.0069(4) C25 0.0159(4) 0.0228(5) 0.0129(4) 0.0014(3) 0.0020(3) 0.0082(4) C26 0.0217(5) 0.0254(5) 0.0154(4) 0.0023(4) 0.0003(4) 0.0106(4) C27 0.0270(5) 0.0332(6) 0.0154(4) 0.0024(4) -0.0027(4) 0.0141(5) C28 0.0240(5) 0.0333(6) 0.0165(5) -0.0038(4) -0.0033(4) 0.0110(5) C29 0.0246(5) 0.0247(5) 0.0234(5) -0.0024(4) -0.0012(4) 0.0085(4) C30 0.0223(5) 0.0231(5) 0.0199(5) 0.0014(4) -0.0010(4) 0.0092(4) C31 0.0146(4) 0.0168(4) 0.0175(4) 0.0042(3) 0.0036(3) 0.0056(3) C32 0.0195(4) 0.0220(5) 0.0188(4) 0.0056(4) 0.0033(3) 0.0090(4) C33 0.0216(5) 0.0251(5) 0.0270(5) 0.0103(4) 0.0023(4) 0.0106(4) C34 0.0265(5) 0.0204(5) 0.0351(6) 0.0076(4) 0.0038(5) 0.0117(4) C35 0.0298(6) 0.0202(5) 0.0272(5) 0.0023(4) 0.0053(4) 0.0116(4) C36 0.0240(5) 0.0194(4) 0.0181(4) 0.0024(3) 0.0031(4) 0.0088(4) _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 . 1.4050(14) yes C1 . C6 . 1.4027(15) yes C1 . C7 . 1.4843(14) yes C2 . C3 . 1.3913(14) yes C2 . H21 . 0.950 no C3 . C4 . 1.3918(17) yes C3 . H31 . 0.950 no C4 . C5 . 1.3924(16) yes C4 . H41 . 0.950 no C5 . C6 . 1.3915(14) yes C5 . H51 . 0.950 no C6 . H61 . 0.950 no C7 . C8 . 1.4017(13) yes C7 . C12 . 1.3985(14) yes C8 . C9 . 1.4041(13) yes C8 . H81 . 0.950 no C9 . C10 . 1.4079(14) yes C9 . C25 . 1.4929(14) yes C10 . C11 . 1.3991(14) yes C10 . C13 . 1.4935(13) yes C11 . C12 . 1.3878(13) yes C11 . H111 . 0.950 no C12 . H121 . 0.950 no C13 . C14 . 1.4076(14) yes C13 . C18 . 1.3982(15) yes C14 . C15 . 1.4045(13) yes C14 . C31 . 1.4907(14) yes C15 . C16 . 1.3991(14) yes C15 . H151 . 0.950 no C16 . C17 . 1.4003(14) yes C16 . C19 . 1.4840(13) yes C17 . C18 . 1.3870(14) yes C17 . H171 . 0.950 no C18 . H181 . 0.950 no C19 . C20 . 1.4000(14) yes C19 . C24 . 1.4033(14) yes C20 . C21 . 1.3943(14) yes C20 . H201 . 0.950 no C21 . C22 . 1.3918(16) yes C21 . H211 . 0.950 no C22 . C23 . 1.3932(16) yes C22 . H221 . 0.950 no C23 . C24 . 1.3943(14) yes C23 . H231 . 0.950 no C24 . H241 . 0.950 no C25 . C26 . 1.3984(15) yes C25 . C30 . 1.3993(15) yes C26 . C27 . 1.3899(15) yes C26 . H261 . 0.950 no C27 . C28 . 1.3895(18) yes C27 . H271 . 0.950 no C28 . C29 . 1.3878(18) yes C28 . H281 . 0.950 no C29 . C30 . 1.3887(15) yes C29 . H291 . 0.950 no C30 . H301 . 0.950 no C31 . C32 . 1.4027(14) yes C31 . C36 . 1.4011(14) yes C32 . C33 . 1.3923(15) yes C32 . H321 . 0.950 no C33 . C34 . 1.3890(17) yes C33 . H331 . 0.950 no C34 . C35 . 1.3918(18) yes C34 . H341 . 0.950 no C35 . C36 . 1.3934(16) yes C35 . H351 . 0.950 no C36 . H361 . 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 . 118.06(9) yes C2 . C1 . C7 . 121.07(9) yes C6 . C1 . C7 . 120.87(9) yes C1 . C2 . C3 . 120.87(10) yes C1 . C2 . H21 . 119.5 no C3 . C2 . H21 . 119.7 no C2 . C3 . C4 . 120.50(10) yes C2 . C3 . H31 . 119.7 no C4 . C3 . H31 . 119.8 no C3 . C4 . C5 . 119.16(10) yes C3 . C4 . H41 . 120.4 no C5 . C4 . H41 . 120.4 no C4 . C5 . C6 . 120.59(10) yes C4 . C5 . H51 . 119.7 no C6 . C5 . H51 . 119.7 no C1 . C6 . C5 . 120.80(10) yes C1 . C6 . H61 . 119.5 no C5 . C6 . H61 . 119.7 no C1 . C7 . C8 . 121.43(9) yes C1 . C7 . C12 . 120.60(9) yes C8 . C7 . C12 . 117.94(9) yes C7 . C8 . C9 . 122.23(9) yes C7 . C8 . H81 . 118.9 no C9 . C8 . H81 . 118.9 no C8 . C9 . C10 . 118.75(9) yes C8 . C9 . C25 . 118.83(9) yes C10 . C9 . C25 . 122.22(9) yes C9 . C10 . C11 . 118.96(9) yes C9 . C10 . C13 . 124.00(9) yes C11 . C10 . C13 . 117.04(9) yes C10 . C11 . C12 . 121.49(9) yes C10 . C11 . H111 . 119.2 no C12 . C11 . H111 . 119.4 no C7 . C12 . C11 . 120.56(9) yes C7 . C12 . H121 . 119.7 no C11 . C12 . H121 . 119.7 no C10 . C13 . C14 . 123.84(9) yes C10 . C13 . C18 . 117.45(9) yes C14 . C13 . C18 . 118.64(9) yes C13 . C14 . C15 . 118.51(9) yes C13 . C14 . C31 . 123.59(9) yes C15 . C14 . C31 . 117.85(9) yes C14 . C15 . C16 . 122.85(9) yes C14 . C15 . H151 . 118.6 no C16 . C15 . H151 . 118.6 no C15 . C16 . C17 . 117.62(9) yes C15 . C16 . C19 . 121.61(9) yes C17 . C16 . C19 . 120.77(9) yes C16 . C17 . C18 . 120.25(10) yes C16 . C17 . H171 . 119.8 no C18 . C17 . H171 . 120.0 no C13 . C18 . C17 . 122.10(10) yes C13 . C18 . H181 . 118.8 no C17 . C18 . H181 . 119.1 no C16 . C19 . C20 . 121.26(9) yes C16 . C19 . C24 . 120.42(9) yes C20 . C19 . C24 . 118.32(9) yes C19 . C20 . C21 . 120.95(10) yes C19 . C20 . H201 . 119.3 no C21 . C20 . H201 . 119.7 no C20 . C21 . C22 . 120.16(10) yes C20 . C21 . H211 . 119.8 no C22 . C21 . H211 . 120.1 no C21 . C22 . C23 . 119.57(10) yes C21 . C22 . H221 . 120.2 no C23 . C22 . H221 . 120.3 no C22 . C23 . C24 . 120.28(10) yes C22 . C23 . H231 . 119.9 no C24 . C23 . H231 . 119.8 no C19 . C24 . C23 . 120.71(10) yes C19 . C24 . H241 . 119.4 no C23 . C24 . H241 . 119.9 no C9 . C25 . C26 . 120.49(9) yes C9 . C25 . C30 . 121.38(9) yes C26 . C25 . C30 . 117.93(9) yes C25 . C26 . C27 . 120.85(11) yes C25 . C26 . H261 . 119.5 no C27 . C26 . H261 . 119.7 no C26 . C27 . C28 . 120.58(11) yes C26 . C27 . H271 . 119.8 no C28 . C27 . H271 . 119.6 no C27 . C28 . C29 . 119.12(10) yes C27 . C28 . H281 . 120.6 no C29 . C28 . H281 . 120.3 no C28 . C29 . C30 . 120.40(11) yes C28 . C29 . H291 . 119.9 no C30 . C29 . H291 . 119.7 no C25 . C30 . C29 . 121.10(11) yes C25 . C30 . H301 . 119.3 no C29 . C30 . H301 . 119.6 no C14 . C31 . C32 . 122.03(9) yes C14 . C31 . C36 . 119.85(9) yes C32 . C31 . C36 . 117.91(10) yes C31 . C32 . C33 . 120.76(10) yes C31 . C32 . H321 . 119.5 no C33 . C32 . H321 . 119.7 no C32 . C33 . C34 . 120.70(10) yes C32 . C33 . H331 . 119.7 no C34 . C33 . H331 . 119.6 no C33 . C34 . C35 . 119.21(11) yes C33 . C34 . H341 . 120.3 no C35 . C34 . H341 . 120.4 no C34 . C35 . C36 . 120.21(11) yes C34 . C35 . H351 . 119.9 no C36 . C35 . H351 . 119.9 no C31 . C36 . C35 . 121.17(10) yes C31 . C36 . H361 . 119.3 no C35 . C36 . H361 . 119.5 no data_fs158 _database_code_depnum_ccdc_archive 'CCDC 918311' #TrackingRef '16646_web_deposit_cif_file_1_FlorianSchluetter_1357558163.fs158.cif' _audit_creation_date 12-03-26 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.5317(7) _cell_length_b 21.0519(9) _cell_length_c 17.7743(8) _cell_angle_alpha 90 _cell_angle_beta 94.802(5) _cell_angle_gamma 90 _cell_volume 2808.3(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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C36.50 H25 Cl3 # Dc = 1.35 Fooo = 1180.00 Mu = 3.52 M = 569.96 # Found Formula = C36.50 H25 Cl3 # Dc = 1.35 FOOO = 1180.00 Mu = 3.52 M = 569.96 _chemical_formula_sum 'C36.50 H25 Cl3' _chemical_formula_moiety 'C36.50 H25 Cl3' _chemical_compound_source ? _chemical_formula_weight 569.96 _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 colourless _exptl_crystal_size_min 0.09 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_max 0.47 _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1180 _exptl_absorpt_coefficient_mu 0.352 # Sheldrick geometric approximatio 0.96 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.97 # 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 8821 _reflns_number_total 6633 _diffrn_reflns_av_R_equivalents 0.035 # Number of reflections with Friedels Law is 6633 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 6584 _diffrn_reflns_theta_min 1.502 _diffrn_reflns_theta_max 27.702 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.209 _diffrn_measured_fraction_theta_full 0.985 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -9 _reflns_limit_h_max 9 _reflns_limit_k_min 0 _reflns_limit_k_max 27 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.51 _refine_diff_density_max 0.54 _refine_ls_number_reflns 3506 _refine_ls_number_restraints 0 _refine_ls_number_parameters 361 #_refine_ls_R_factor_ref 0.0464 _refine_ls_wR_factor_ref 0.0571 _refine_ls_goodness_of_fit_ref 1.1215 #_reflns_number_all 4746 _refine_ls_R_factor_all 0.0856 _refine_ls_wR_factor_all 0.3077 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.7\s(I) _reflns_number_gt 3506 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_gt 0.0571 _refine_ls_shift/su_max 0.000454 # 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: 0.602 0.658 0.208 ; # 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 Cl1 Cl 0.63560(8) 0.14082(3) 0.40070(3) 0.0477 1.0000 Uani . . . . . . Cl2 Cl 1.05100(8) 0.21888(3) 0.33892(3) 0.0463 1.0000 Uani . . . . . . Cl3 Cl 0.15572(11) 0.01806(4) 0.54822(5) 0.0719 1.0000 Uani . . . . . . C1 C 0.3879(3) 0.21443(9) 0.13298(11) 0.0336 1.0000 Uani . . . . . . C2 C 0.4148(3) 0.21811(9) 0.05747(11) 0.0348 1.0000 Uani . . . . . . C3 C 0.3394(3) 0.26419(9) 0.00581(12) 0.0389 1.0000 Uani . . . . . . C4 C 0.2358(3) 0.30695(10) 0.03733(13) 0.0420 1.0000 Uani . . . . . . C5 C 0.1925(3) 0.30654(10) 0.11104(13) 0.0438 1.0000 Uani . . . . . . C6 C 0.2717(3) 0.26323(9) 0.15808(13) 0.0394 1.0000 Uani . . . . . . C7 C 0.4678(3) 0.16141(9) 0.18230(11) 0.0326 1.0000 Uani . . . . . . C8 C 0.5175(3) 0.17651(9) 0.26000(11) 0.0355 1.0000 Uani . . . . . . C9 C 0.5891(3) 0.12970(9) 0.30386(12) 0.0365 1.0000 Uani . . . . . . C10 C 0.6398(3) 0.06960(9) 0.27206(11) 0.0348 1.0000 Uani . . . . . . C11 C 0.5930(3) 0.06102(9) 0.19460(11) 0.0335 1.0000 Uani . . . . . . C12 C 0.5110(2) 0.10744(8) 0.15055(11) 0.0323 1.0000 Uani . . . . . . C13 C 0.6539(3) -0.00014(10) 0.16151(11) 0.0360 1.0000 Uani . . . . . . C14 C 0.6319(3) -0.05953(11) 0.20351(13) 0.0430 1.0000 Uani . . . . . . C15 C 0.6798(3) -0.11581(11) 0.17274(13) 0.0429 1.0000 Uani . . . . . . C16 C 0.7529(3) -0.11935(10) 0.10612(12) 0.0377 1.0000 Uani . . . . . . C17 C 0.7943(3) -0.06327(9) 0.06707(11) 0.0346 1.0000 Uani . . . . . . C18 C 0.7378(3) -0.00159(9) 0.09581(11) 0.0323 1.0000 Uani . . . . . . C19 C 0.7855(3) 0.05615(9) 0.05033(11) 0.0315 1.0000 Uani . . . . . . C20 C 0.7204(3) 0.06290(9) -0.02134(11) 0.0350 1.0000 Uani . . . . . . C21 C 0.7538(3) 0.11329(10) -0.06400(12) 0.0400 1.0000 Uani . . . . . . C22 C 0.8538(3) 0.16026(10) -0.03150(12) 0.0382 1.0000 Uani . . . . . . C23 C 0.9281(2) 0.15864(9) 0.03947(11) 0.0312 1.0000 Uani . . . . . . C24 C 0.8955(2) 0.10514(9) 0.08521(11) 0.0296 1.0000 Uani . . . . . . C25 C 0.9843(3) 0.10228(9) 0.16342(11) 0.0326 1.0000 Uani . . . . . . C26 C 0.9791(2) 0.15738(8) 0.20976(11) 0.0300 1.0000 Uani . . . . . . C27 C 1.0585(3) 0.14891(9) 0.28252(11) 0.0328 1.0000 Uani . . . . . . C28 C 1.1276(3) 0.09617(9) 0.31325(11) 0.0334 1.0000 Uani . . . . . . C29 C 1.1308(3) 0.04355(9) 0.26671(10) 0.0324 1.0000 Uani . . . . . . C30 C 1.0701(3) 0.04652(9) 0.19677(11) 0.0335 1.0000 Uani . . . . . . C31 C 1.2099(3) -0.01728(10) 0.29895(12) 0.0376 1.0000 Uani . . . . . . C32 C 1.3326(3) -0.02533(11) 0.35961(13) 0.0444 1.0000 Uani . . . . . . C33 C 1.3963(4) -0.07719(12) 0.39378(15) 0.0540 1.0000 Uani . . . . . . C34 C 1.3385(4) -0.13234(12) 0.35756(15) 0.0550 1.0000 Uani . . . . . . C35 C 1.2092(4) -0.13647(11) 0.29539(14) 0.0518 1.0000 Uani . . . . . . C36 C 1.1375(3) -0.07559(10) 0.26340(12) 0.0433 1.0000 Uani . . . . . . C41 C -0.0728(9) 0.0454(3) 0.4921(4) 0.0733 0.5000 Uani . . . . . . H21 H 0.4975 0.1889 0.0394 0.0385 1.0000 Uiso R . . . . . H31 H 0.3615 0.2635 -0.0460 0.0460 1.0000 Uiso R . . . . . H41 H 0.1853 0.3398 0.0057 0.0431 1.0000 Uiso R . . . . . H51 H 0.1112 0.3360 0.1297 0.0462 1.0000 Uiso R . . . . . H61 H 0.2534 0.2644 0.2103 0.0364 1.0000 Uiso R . . . . . H81 H 0.4921 0.2167 0.2810 0.0296 1.0000 Uiso R . . . . . H101 H 0.7026 0.0385 0.3025 0.0341 1.0000 Uiso R . . . . . H121 H 0.4824 0.1002 0.0982 0.0300 1.0000 Uiso R . . . . . H141 H 0.5828 -0.0579 0.2510 0.0339 1.0000 Uiso R . . . . . H151 H 0.6542 -0.1541 0.1980 0.0539 1.0000 Uiso R . . . . . H161 H 0.7864 -0.1595 0.0874 0.0334 1.0000 Uiso R . . . . . H201 H 0.6452 0.0299 -0.0419 0.0339 1.0000 Uiso R . . . . . H211 H 0.7073 0.1161 -0.1153 0.0449 1.0000 Uiso R . . . . . H221 H 0.8716 0.1979 -0.0594 0.0376 1.0000 Uiso R . . . . . H231 H 1.0019 0.1921 0.0599 0.0330 1.0000 Uiso R . . . . . H261 H 0.9164 0.1946 0.1931 0.0406 1.0000 Uiso R . . . . . H281 H 1.1713 0.0936 0.3649 0.0331 1.0000 Uiso R . . . . . H301 H 1.0723 0.0100 0.1655 0.0328 1.0000 Uiso R . . . . . H321 H 1.3767 0.0137 0.3805 0.0543 1.0000 Uiso R . . . . . H331 H 1.4747 -0.0773 0.4385 0.0576 1.0000 Uiso R . . . . . H341 H 1.3898 -0.1714 0.3749 0.0560 1.0000 Uiso R . . . . . H351 H 1.1643 -0.1754 0.2744 0.0487 1.0000 Uiso R . . . . . H361 H 1.0531 -0.0748 0.2206 0.0450 1.0000 Uiso R . . . . . H411 H -0.1532 0.0667 0.5264 0.0369 0.5000 Uiso R . . . . . H412 H -0.0419 0.0759 0.4521 0.0369 0.5000 Uiso R . . . . . H171 H 0.8574 -0.0655 0.0231 0.0414 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 Cl1 0.0608(4) 0.0465(3) 0.0372(3) -0.0028(2) 0.0125(2) 0.0108(2) Cl2 0.0611(4) 0.0390(3) 0.0389(3) -0.0100(2) 0.0042(2) -0.0046(2) Cl3 0.0724(5) 0.0690(5) 0.0728(5) 0.0051(3) -0.0025(4) 0.0049(4) C1 0.0350(10) 0.0252(9) 0.0418(10) -0.0023(7) 0.0109(8) -0.0030(7) C2 0.0377(10) 0.0284(9) 0.0394(10) -0.0015(7) 0.0100(8) -0.0039(7) C3 0.0432(11) 0.0311(10) 0.0433(11) 0.0006(8) 0.0085(9) -0.0001(8) C4 0.0480(12) 0.0325(10) 0.0465(11) 0.0013(8) 0.0093(9) 0.0036(9) C5 0.0515(13) 0.0321(10) 0.0494(12) 0.0003(8) 0.0133(10) 0.0050(9) C6 0.0455(11) 0.0293(9) 0.0448(11) -0.0028(8) 0.0114(9) 0.0018(8) C7 0.0326(9) 0.0278(9) 0.0388(10) -0.0025(7) 0.0122(8) -0.0047(7) C8 0.0395(10) 0.0290(9) 0.0396(10) -0.0038(8) 0.0119(8) -0.0008(8) C9 0.0402(10) 0.0335(10) 0.0376(10) -0.0010(8) 0.0138(8) 0.0000(8) C10 0.0366(10) 0.0311(10) 0.0384(10) -0.0005(7) 0.0139(8) -0.0006(8) C11 0.0344(9) 0.0278(9) 0.0400(10) -0.0016(7) 0.0127(8) -0.0023(7) C12 0.0328(9) 0.0263(9) 0.0392(10) -0.0034(7) 0.0112(8) -0.0055(7) C13 0.0322(10) 0.0432(11) 0.0337(9) -0.0065(8) 0.0095(8) -0.0071(8) C14 0.0443(12) 0.0487(12) 0.0380(11) -0.0002(9) 0.0154(9) -0.0117(10) C15 0.0430(11) 0.0437(11) 0.0433(12) 0.0068(9) 0.0110(9) -0.0054(9) C16 0.0364(10) 0.0349(10) 0.0425(11) 0.0058(8) 0.0070(9) 0.0013(8) C17 0.0396(10) 0.0335(10) 0.0320(9) 0.0017(7) 0.0104(8) 0.0050(8) C18 0.0323(9) 0.0346(10) 0.0311(9) -0.0013(7) 0.0083(7) 0.0006(7) C19 0.0306(9) 0.0325(9) 0.0321(9) -0.0010(7) 0.0056(7) 0.0036(7) C20 0.0354(10) 0.0348(10) 0.0343(10) 0.0011(7) 0.0008(8) 0.0060(8) C21 0.0385(11) 0.0405(11) 0.0400(11) 0.0080(8) -0.0023(9) 0.0068(9) C22 0.0278(9) 0.0380(10) 0.0487(12) 0.0102(8) 0.0021(8) 0.0069(8) C23 0.0142(7) 0.0345(10) 0.0455(10) 0.0042(7) 0.0051(7) 0.0075(6) C24 0.0195(8) 0.0347(9) 0.0352(9) -0.0002(7) 0.0068(7) 0.0047(7) C25 0.0400(10) 0.0269(9) 0.0326(9) -0.0019(7) 0.0139(8) -0.0027(7) C26 0.0299(9) 0.0285(9) 0.0335(9) -0.0043(7) 0.0129(7) -0.0054(7) C27 0.0321(9) 0.0345(10) 0.0334(9) -0.0031(7) 0.0119(8) -0.0080(8) C28 0.0331(10) 0.0350(10) 0.0336(10) 0.0003(7) 0.0120(8) -0.0076(7) C29 0.0330(9) 0.0336(10) 0.0330(9) 0.0028(7) 0.0162(8) -0.0046(7) C30 0.0423(11) 0.0282(9) 0.0323(10) 0.0009(7) 0.0166(8) -0.0015(8) C31 0.0401(11) 0.0384(11) 0.0364(10) 0.0066(8) 0.0150(9) -0.0020(8) C32 0.0442(12) 0.0450(12) 0.0448(12) 0.0121(9) 0.0080(10) -0.0021(9) C33 0.0539(14) 0.0490(13) 0.0596(15) 0.0182(11) 0.0072(12) 0.0004(11) C34 0.0661(16) 0.0451(13) 0.0548(14) 0.0184(11) 0.0106(12) 0.0036(11) C35 0.0731(16) 0.0377(12) 0.0458(13) 0.0117(9) 0.0124(11) 0.0056(11) C36 0.0609(14) 0.0327(10) 0.0379(11) 0.0071(8) 0.0123(10) 0.0007(9) C41 0.073(4) 0.074(4) 0.071(4) 0.005(3) -0.005(3) 0.002(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 Cl1 . C9 . 1.743(2) yes Cl2 . C27 . 1.7854(19) yes Cl3 . C41 2_556 1.616(6) yes Cl3 . C41 . 2.000(6) yes C1 . C2 . 1.376(3) yes C1 . C6 . 1.444(3) yes C1 . C7 . 1.513(3) yes C2 . C3 . 1.421(3) yes C2 . H21 . 0.950 no C3 . C4 . 1.344(3) yes C3 . H31 . 0.950 no C4 . C5 . 1.377(3) yes C4 . H41 . 0.950 no C5 . C6 . 1.343(3) yes C5 . H51 . 0.950 no C6 . H61 . 0.950 no C7 . C8 . 1.436(3) yes C7 . C12 . 1.321(3) yes C8 . C9 . 1.341(3) yes C8 . H81 . 0.950 no C9 . C10 . 1.450(3) yes C10 . C11 . 1.404(3) yes C10 . H101 . 0.950 no C11 . C12 . 1.367(3) yes C11 . C13 . 1.503(3) yes C12 . H121 . 0.950 no C13 . C14 . 1.473(3) yes C13 . C18 . 1.374(3) yes C14 . C15 . 1.366(3) yes C14 . H141 . 0.950 no C15 . C16 . 1.349(3) yes C15 . H151 . 0.950 no C16 . C17 . 1.417(3) yes C16 . H161 . 0.950 no C17 . C18 . 1.471(3) yes C17 . H171 . 0.950 no C18 . C19 . 1.519(3) yes C19 . C20 . 1.334(3) yes C19 . C24 . 1.431(3) yes C20 . C21 . 1.340(3) yes C20 . H201 . 0.950 no C21 . C22 . 1.344(3) yes C21 . H211 . 0.950 no C22 . C23 . 1.337(3) yes C22 . H221 . 0.950 no C23 . C24 . 1.422(3) yes C23 . H231 . 0.950 no C24 . C25 . 1.492(3) yes C25 . C26 . 1.425(2) yes C25 . C30 . 1.443(3) yes C26 . C27 . 1.390(3) yes C26 . H261 . 0.950 no C27 . C28 . 1.325(3) yes C28 . C29 . 1.384(3) yes C28 . H281 . 0.950 no C29 . C30 . 1.290(3) yes C29 . C31 . 1.505(3) yes C30 . H301 . 0.950 no C31 . C32 . 1.370(3) yes C31 . C36 . 1.465(3) yes C32 . C33 . 1.320(3) yes C32 . H321 . 0.950 no C33 . C34 . 1.380(4) yes C33 . H331 . 0.950 no C34 . C35 . 1.413(4) yes C34 . H341 . 0.950 no C35 . C36 . 1.485(3) yes C35 . H351 . 0.950 no C36 . H361 . 0.950 no C41 . H411 . 1.000 no C41 . H412 . 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 C41 2_556 Cl3 . C41 . 74.4(3) yes C2 . C1 . C6 . 113.81(18) yes C2 . C1 . C7 . 121.53(18) yes C6 . C1 . C7 . 124.59(18) yes C1 . C2 . C3 . 125.82(19) yes C1 . C2 . H21 . 116.6 no C3 . C2 . H21 . 117.4 no C2 . C3 . C4 . 113.7(2) yes C2 . C3 . H31 . 121.6 no C4 . C3 . H31 . 124.7 no C3 . C4 . C5 . 125.8(2) yes C3 . C4 . H41 . 117.3 no C5 . C4 . H41 . 116.9 no C4 . C5 . C6 . 117.9(2) yes C4 . C5 . H51 . 122.6 no C6 . C5 . H51 . 119.4 no C1 . C6 . C5 . 122.7(2) yes C1 . C6 . H61 . 117.5 no C5 . C6 . H61 . 119.8 no C1 . C7 . C8 . 116.94(16) yes C1 . C7 . C12 . 119.15(18) yes C8 . C7 . C12 . 123.19(18) yes C7 . C8 . C9 . 117.14(18) yes C7 . C8 . H81 . 122.0 no C9 . C8 . H81 . 120.6 no Cl1 . C9 . C8 . 120.87(16) yes Cl1 . C9 . C10 . 117.66(15) yes C8 . C9 . C10 . 121.38(19) yes C9 . C10 . C11 . 116.22(18) yes C9 . C10 . H101 . 120.9 no C11 . C10 . H101 . 122.9 no C10 . C11 . C12 . 122.27(18) yes C10 . C11 . C13 . 115.74(17) yes C12 . C11 . C13 . 121.76(18) yes C11 . C12 . C7 . 119.06(19) yes C11 . C12 . H121 . 120.1 no C7 . C12 . H121 . 120.9 no C11 . C13 . C14 . 118.57(17) yes C11 . C13 . C18 . 121.91(18) yes C14 . C13 . C18 . 119.41(18) yes C13 . C14 . C15 . 119.3(2) yes C13 . C14 . H141 . 119.3 no C15 . C14 . H141 . 121.5 no C14 . C15 . C16 . 122.7(2) yes C14 . C15 . H151 . 118.5 no C16 . C15 . H151 . 118.8 no C15 . C16 . C17 . 120.43(19) yes C15 . C16 . H161 . 119.7 no C17 . C16 . H161 . 119.6 no C16 . C17 . C18 . 118.90(18) yes C16 . C17 . H171 . 120.6 no C18 . C17 . H171 . 120.5 no C17 . C18 . C13 . 118.80(17) yes C17 . C18 . C19 . 115.67(16) yes C13 . C18 . C19 . 125.48(17) yes C18 . C19 . C20 . 120.59(17) yes C18 . C19 . C24 . 120.01(16) yes C20 . C19 . C24 . 119.35(18) yes C19 . C20 . C21 . 123.6(2) yes C19 . C20 . H201 . 116.7 no C21 . C20 . H201 . 119.7 no C20 . C21 . C22 . 117.67(19) yes C20 . C21 . H211 . 121.3 no C22 . C21 . H211 . 121.0 no C21 . C22 . C23 . 124.20(19) yes C21 . C22 . H221 . 119.2 no C23 . C22 . H221 . 116.6 no C22 . C23 . C24 . 118.76(18) yes C22 . C23 . H231 . 121.8 no C24 . C23 . H231 . 119.5 no C19 . C24 . C23 . 116.37(17) yes C19 . C24 . C25 . 124.91(16) yes C23 . C24 . C25 . 118.64(16) yes C24 . C25 . C26 . 118.28(17) yes C24 . C25 . C30 . 124.45(16) yes C26 . C25 . C30 . 117.23(17) yes C25 . C26 . C27 . 113.76(17) yes C25 . C26 . H261 . 121.9 no C27 . C26 . H261 . 124.1 no Cl2 . C27 . C26 . 112.66(14) yes Cl2 . C27 . C28 . 119.33(15) yes C26 . C27 . C28 . 127.93(17) yes C27 . C28 . C29 . 116.77(18) yes C27 . C28 . H281 . 122.5 no C29 . C28 . H281 . 120.7 no C28 . C29 . C30 . 120.98(19) yes C28 . C29 . C31 . 118.65(17) yes C30 . C29 . C31 . 120.36(18) yes C25 . C30 . C29 . 123.09(18) yes C25 . C30 . H301 . 116.6 no C29 . C30 . H301 . 120.1 no C29 . C31 . C32 . 128.61(19) yes C29 . C31 . C36 . 115.31(18) yes C32 . C31 . C36 . 115.96(19) yes C31 . C32 . C33 . 131.3(2) yes C31 . C32 . H321 . 113.1 no C33 . C32 . H321 . 115.7 no C32 . C33 . C34 . 113.1(2) yes C32 . C33 . H331 . 124.3 no C34 . C33 . H331 . 122.6 no C33 . C34 . C35 . 125.9(2) yes C33 . C34 . H341 . 118.2 no C35 . C34 . H341 . 115.8 no C34 . C35 . C36 . 116.8(2) yes C34 . C35 . H351 . 124.0 no C36 . C35 . H351 . 119.2 no C35 . C36 . C31 . 116.6(2) yes C35 . C36 . H361 . 121.2 no C31 . C36 . H361 . 122.1 no Cl3 . C41 . Cl3 2_556 105.6(3) yes Cl3 . C41 . H411 . 111.4 no Cl3 2_556 C41 . H411 . 114.2 no Cl3 . C41 . H412 . 107.3 no Cl3 2_556 C41 . H412 . 108.6 no H411 . C41 . H412 . 109.5 no data_fs288n _database_code_depnum_ccdc_archive 'CCDC 918312' #TrackingRef '16647_web_deposit_cif_file_2_FlorianSchluetter_1357558163.fs228.cif' _audit_creation_date 12-04-11 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 7.3789(2) _cell_length_b 22.1571(8) _cell_length_c 16.3043(5) _cell_angle_alpha 90 _cell_angle_beta 102.0571(18) _cell_angle_gamma 90 _cell_volume 2606.87(14) _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' _cell_formula_units_Z 4 # Given Formula = C38 H30 # Dc = 1.24 Fooo = 1032.00 Mu = 0.70 M = 243.33 # Found Formula = C38 H30 # Dc = 1.24 FOOO = 1032.00 Mu = 0.70 M = 243.33 _chemical_formula_sum 'C38 H30' _chemical_formula_moiety 'C38 H30' _chemical_compound_source ? _chemical_formula_weight 486.66 _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 colourless _exptl_crystal_size_min 0.11 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.44 _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.070 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_absorpt_correction_T_min 0.91 _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 15957 _reflns_number_total 3797 _diffrn_reflns_av_R_equivalents 0.087 # Number of reflections with Friedels Law is 3797 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 3810 _diffrn_reflns_theta_min 1.838 _diffrn_reflns_theta_max 30.029 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.528 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 31 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.23 _refine_diff_density_max 0.35 _refine_ls_number_reflns 2439 _refine_ls_number_restraints 0 _refine_ls_number_parameters 172 #_refine_ls_R_factor_ref 0.0423 _refine_ls_wR_factor_ref 0.0502 _refine_ls_goodness_of_fit_ref 1.1061 #_reflns_number_all 3785 _refine_ls_R_factor_all 0.0733 _refine_ls_wR_factor_all 0.0661 # 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 2439 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_gt 0.0502 _refine_ls_shift/su_max 0.000232 # 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: 1.27 0.475 0.810 ; # 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 0.55489(16) 0.17144(5) 0.21647(7) 0.0156 1.0000 Uani . . . . . . C2 C 0.68516(16) 0.21749(5) 0.21312(7) 0.0161 1.0000 Uani . . . . . . C3 C 0.78575(17) 0.21709(6) 0.14916(8) 0.0178 1.0000 Uani . . . . . . C4 C 0.75971(17) 0.17255(6) 0.08771(7) 0.0187 1.0000 Uani . . . . . . C5 C 0.63183(17) 0.12707(6) 0.09198(8) 0.0181 1.0000 Uani . . . . . . C6 C 0.52867(16) 0.12561(5) 0.15494(8) 0.0166 1.0000 Uani . . . . . . C7 C 0.39089(17) 0.07569(5) 0.15058(7) 0.0180 1.0000 Uani . . . . . . C8 C 0.20836(18) 0.08523(6) 0.15913(8) 0.0218 1.0000 Uani . . . . . . C9 C 0.08087(19) 0.03804(6) 0.14816(9) 0.0256 1.0000 Uani . . . . . . C10 C 0.1335(2) -0.01948(6) 0.12882(10) 0.0276 1.0000 Uani . . . . . . C11 C 0.3143(2) -0.03012(6) 0.12161(9) 0.0269 1.0000 Uani . . . . . . C12 C 0.44198(19) 0.01694(6) 0.13241(9) 0.0223 1.0000 Uani . . . . . . C13 C 0.71940(16) 0.26826(5) 0.27474(7) 0.0166 1.0000 Uani . . . . . . C14 C 0.74581(17) 0.25914(6) 0.36140(8) 0.0191 1.0000 Uani . . . . . . C15 C 0.78174(18) 0.30721(6) 0.41716(8) 0.0215 1.0000 Uani . . . . . . C16 C 0.79034(19) 0.36577(6) 0.38756(9) 0.0237 1.0000 Uani . . . . . . C17 C 0.7649(2) 0.37576(6) 0.30176(9) 0.0263 1.0000 Uani . . . . . . C18 C 0.73049(19) 0.32746(6) 0.24622(8) 0.0226 1.0000 Uani . . . . . . C19 C 0.86173(19) 0.17335(6) 0.01670(8) 0.0234 1.0000 Uani . . . . . . H31 H 0.8743 0.2480 0.1477 0.0244 1.0000 Uiso R . . . . . H51 H 0.6141 0.0960 0.0509 0.0243 1.0000 Uiso R . . . . . H81 H 0.1713 0.1244 0.1729 0.0295 1.0000 Uiso R . . . . . H91 H -0.0428 0.0453 0.1538 0.0340 1.0000 Uiso R . . . . . H101 H 0.0458 -0.0515 0.1207 0.0370 1.0000 Uiso R . . . . . H111 H 0.3514 -0.0695 0.1089 0.0360 1.0000 Uiso R . . . . . H121 H 0.5660 0.0092 0.1277 0.0302 1.0000 Uiso R . . . . . H141 H 0.7386 0.2194 0.3824 0.0260 1.0000 Uiso R . . . . . H151 H 0.8003 0.3000 0.4758 0.0287 1.0000 Uiso R . . . . . H161 H 0.8134 0.3987 0.4257 0.0320 1.0000 Uiso R . . . . . H171 H 0.7716 0.4156 0.2811 0.0352 1.0000 Uiso R . . . . . H181 H 0.7136 0.3348 0.1877 0.0304 1.0000 Uiso R . . . . . H191 H 0.9314 0.2096 0.0173 0.0500 1.0000 Uiso R . . . . . H192 H 0.9472 0.1398 0.0229 0.0500 1.0000 Uiso R . . . . . H193 H 0.7743 0.1702 -0.0357 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(5) 0.0159(5) 0.0155(5) 0.0007(4) 0.0034(4) 0.0011(4) C2 0.0157(5) 0.0163(5) 0.0162(5) 0.0013(4) 0.0034(4) 0.0014(4) C3 0.0165(5) 0.0190(5) 0.0186(5) 0.0022(4) 0.0052(4) -0.0001(4) C4 0.0180(6) 0.0213(6) 0.0174(5) 0.0027(5) 0.0053(4) 0.0032(4) C5 0.0194(6) 0.0184(5) 0.0169(5) -0.0012(4) 0.0049(4) 0.0023(4) C6 0.0158(5) 0.0162(5) 0.0181(5) 0.0003(4) 0.0042(4) 0.0007(4) C7 0.0204(5) 0.0166(5) 0.0172(5) 0.0000(4) 0.0042(4) -0.0008(4) C8 0.0204(6) 0.0201(6) 0.0249(6) 0.0001(5) 0.0043(5) 0.0004(5) C9 0.0190(6) 0.0262(7) 0.0314(7) 0.0009(5) 0.0051(5) -0.0023(5) C10 0.0277(7) 0.0221(6) 0.0325(7) -0.0003(5) 0.0051(5) -0.0072(5) C11 0.0316(7) 0.0179(6) 0.0319(7) -0.0032(5) 0.0084(5) -0.0026(5) C12 0.0224(6) 0.0184(6) 0.0272(6) -0.0013(5) 0.0075(5) 0.0008(5) C13 0.0147(5) 0.0175(5) 0.0181(5) 0.0000(4) 0.0048(4) -0.0013(4) C14 0.0198(6) 0.0192(6) 0.0187(5) 0.0008(4) 0.0051(4) -0.0008(4) C15 0.0228(6) 0.0239(6) 0.0184(6) -0.0013(5) 0.0058(4) -0.0017(5) C16 0.0248(6) 0.0204(6) 0.0254(6) -0.0051(5) 0.0039(5) -0.0028(5) C17 0.0338(7) 0.0192(6) 0.0252(6) 0.0006(5) 0.0044(5) -0.0044(5) C18 0.0271(7) 0.0203(6) 0.0201(6) 0.0011(5) 0.0041(5) -0.0039(5) C19 0.0253(7) 0.0272(6) 0.0200(6) -0.0005(5) 0.0096(5) -0.0009(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 C1 . C1 5_655 1.490(2) yes C1 . C2 . 1.4107(16) yes C1 . C6 . 1.4122(16) yes C2 . C3 . 1.4007(16) yes C2 . C13 . 1.4940(17) yes C3 . C4 . 1.3908(17) yes C3 . H31 . 0.950 no C4 . C5 . 1.3921(17) yes C4 . C19 . 1.5071(17) yes C5 . C6 . 1.4002(16) yes C5 . H51 . 0.950 no C6 . C7 . 1.4940(17) yes C7 . C8 . 1.3989(17) yes C7 . C12 . 1.4037(17) yes C8 . C9 . 1.3928(19) yes C8 . H81 . 0.950 no C9 . C10 . 1.388(2) yes C9 . H91 . 0.950 no C10 . C11 . 1.384(2) yes C10 . H101 . 0.950 no C11 . C12 . 1.3915(19) yes C11 . H111 . 0.950 no C12 . H121 . 0.950 no C13 . C14 . 1.4001(17) yes C13 . C18 . 1.3999(17) yes C14 . C15 . 1.3896(18) yes C14 . H141 . 0.950 no C15 . C16 . 1.3904(19) yes C15 . H151 . 0.950 no C16 . C17 . 1.390(2) yes C16 . H161 . 0.950 no C17 . C18 . 1.3906(19) yes C17 . H171 . 0.950 no C18 . H181 . 0.950 no C19 . H191 . 0.953 no C19 . H192 . 0.967 no C19 . H193 . 0.960 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 5_655 C1 . C2 . 120.50(9) yes C1 5_655 C1 . C6 . 120.42(9) yes C2 . C1 . C6 . 119.08(10) yes C1 . C2 . C3 . 119.70(11) yes C1 . C2 . C13 . 122.64(10) yes C3 . C2 . C13 . 117.64(11) yes C2 . C3 . C4 . 121.73(12) yes C2 . C3 . H31 . 119.2 no C4 . C3 . H31 . 119.1 no C3 . C4 . C5 . 118.07(11) yes C3 . C4 . C19 . 121.94(11) yes C5 . C4 . C19 . 119.97(11) yes C4 . C5 . C6 . 122.10(11) yes C4 . C5 . H51 . 118.9 no C6 . C5 . H51 . 119.0 no C1 . C6 . C5 . 119.30(11) yes C1 . C6 . C7 . 123.86(11) yes C5 . C6 . C7 . 116.81(11) yes C6 . C7 . C8 . 122.90(11) yes C6 . C7 . C12 . 119.11(11) yes C8 . C7 . C12 . 117.89(12) yes C7 . C8 . C9 . 120.82(12) yes C7 . C8 . H81 . 119.5 no C9 . C8 . H81 . 119.7 no C8 . C9 . C10 . 120.35(13) yes C8 . C9 . H91 . 119.8 no C10 . C9 . H91 . 119.8 no C9 . C10 . C11 . 119.74(13) yes C9 . C10 . H101 . 120.1 no C11 . C10 . H101 . 120.1 no C10 . C11 . C12 . 120.06(13) yes C10 . C11 . H111 . 120.1 no C12 . C11 . H111 . 119.9 no C7 . C12 . C11 . 121.13(12) yes C7 . C12 . H121 . 119.3 no C11 . C12 . H121 . 119.6 no C2 . C13 . C14 . 122.57(11) yes C2 . C13 . C18 . 119.71(11) yes C14 . C13 . C18 . 117.71(11) yes C13 . C14 . C15 . 121.13(12) yes C13 . C14 . H141 . 119.4 no C15 . C14 . H141 . 119.5 no C14 . C15 . C16 . 120.31(12) yes C14 . C15 . H151 . 119.8 no C16 . C15 . H151 . 119.9 no C15 . C16 . C17 . 119.44(12) yes C15 . C16 . H161 . 120.2 no C17 . C16 . H161 . 120.3 no C16 . C17 . C18 . 120.06(12) yes C16 . C17 . H171 . 119.9 no C18 . C17 . H171 . 120.0 no C13 . C18 . C17 . 121.35(12) yes C13 . C18 . H181 . 119.3 no C17 . C18 . H181 . 119.3 no C4 . C19 . H191 . 110.9 no C4 . C19 . H192 . 109.3 no H191 . C19 . H192 . 108.0 no C4 . C19 . H193 . 109.4 no H191 . C19 . H193 . 109.4 no H192 . C19 . H193 . 109.8 no data_fs230_250 _database_code_depnum_ccdc_archive 'CCDC 918313' #TrackingRef '16648_web_deposit_cif_file_3_FlorianSchluetter_1357558163.fs230_250.cif' _audit_creation_date 12-11-14 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 13.8723(4) _cell_length_b 17.3314(3) _cell_length_c 37.5890(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 9037.4(3) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'F d d d ' _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 x+1/2,y,z+1/2 -x+1/2,-y,-z+1/2 x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y+1/4,z+1/4 x,-y+1/4,-z+1/4 -x,y+3/4,z+3/4 x,-y+3/4,-z+3/4 -x+1/2,y+1/4,z+3/4 x+1/2,-y+1/4,-z+3/4 -x+1/2,y+3/4,z+1/4 x+1/2,-y+3/4,-z+1/4 x+1/4,-y,z+1/4 -x+1/4,y,-z+1/4 x+1/4,-y+1/2,z+3/4 -x+1/4,y+1/2,-z+3/4 x+3/4,-y,z+3/4 -x+3/4,y,-z+3/4 x+3/4,-y+1/2,z+1/4 -x+3/4,y+1/2,-z+1/4 -x+1/4,-y+3/4,z+1/2 x+1/4,y+3/4,-z+1/2 -x+1/4,-y+5/4,z+1 x+1/4,y+5/4,-z+1 -x+3/4,-y+3/4,z+1 x+3/4,y+3/4,-z+1 -x+3/4,-y+5/4,z+1/2 x+3/4,y+5/4,-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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C52 H56 Cl2 # Dc = 1.11 Fooo = 3216.00 Mu = 1.76 M = 187.98 # Found Formula = C52 H56 Cl2 # Dc = 1.11 FOOO = 3216.00 Mu = 1.76 M = 187.98 _chemical_formula_sum 'C52 H56 Cl2' _chemical_formula_moiety 'C52 H56 Cl2' _chemical_compound_source ? _chemical_formula_weight 751.92 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 250 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.13 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.42 _exptl_crystal_density_diffrn 1.105 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 3216 _exptl_absorpt_coefficient_mu 0.176 # Sheldrick geometric approximatio 0.97 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SORTAV (Blessing)' _exptl_absorpt_correction_T_min 0.93 _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 250 _diffrn_reflns_number 19728 _reflns_number_total 2593 _diffrn_reflns_av_R_equivalents 0.062 # Number of reflections with Friedels Law is 2593 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2590 _diffrn_reflns_theta_min 1.957 _diffrn_reflns_theta_max 27.482 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.482 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -48 _diffrn_reflns_limit_l_max 33 _reflns_limit_h_min 0 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 22 _reflns_limit_l_min 0 _reflns_limit_l_max 48 _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 0.24 _refine_ls_number_reflns 1476 _refine_ls_number_restraints 0 _refine_ls_number_parameters 124 #_refine_ls_R_factor_ref 0.0601 _refine_ls_wR_factor_ref 0.0766 _refine_ls_goodness_of_fit_ref 1.0121 #_reflns_number_all 2584 _refine_ls_R_factor_all 0.1039 _refine_ls_wR_factor_all 0.1617 # 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 1476 _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_gt 0.0766 _refine_ls_shift/su_max 0.000393 # 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: 3.89 2.20 3.06 ; #_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 C1 C 0.3799(2) 0.6250 0.1250 0.0678 1.0000 Uani S T . . . . C2 C 0.33132(14) 0.56632(15) 0.10821(6) 0.0651 1.0000 Uani . . . . . . C3 C 0.23040(14) 0.56525(13) 0.10792(5) 0.0557 1.0000 Uani . . . . . . C4 C 0.17912(16) 0.6250 0.1250 0.0516 1.0000 Uani S T . . . . C5 C 0.18368(14) 0.49898(13) 0.08944(5) 0.0551 1.0000 Uani . . . . . . C6 C 0.21898(17) 0.42482(14) 0.09474(7) 0.0693 1.0000 Uani . . . . . . C7 C 0.18120(19) 0.36235(14) 0.07666(7) 0.0730 1.0000 Uani . . . . . . C8 C 0.10687(17) 0.37011(14) 0.05239(6) 0.0645 1.0000 Uani . . . . . . C9 C 0.07074(15) 0.44485(13) 0.04760(6) 0.0613 1.0000 Uani . . . . . . C10 C 0.10825(14) 0.50759(13) 0.06544(5) 0.0554 1.0000 Uani . . . . . . C11 C 0.0649(2) 0.30229(15) 0.03175(10) 0.0908 1.0000 Uani . . . . . . C12 C 0.0525(4) 0.3212(2) -0.00611(12) 0.1730 1.0000 Uani . . . . . . C13 C 0.1235(4) 0.2290(2) 0.03577(14) 0.1316 1.0000 Uani . . . . . . C14 C -0.0354(3) 0.2843(3) 0.0475(2) 0.1962 1.0000 Uani . . . . . . Cl1 Cl 0.50506(6) 0.6250 0.1250 0.0985 1.0000 Uani S T . . . . H21 H 0.3665 0.5266 0.0966 0.0726 1.0000 Uiso R . . . . . H61 H 0.2711 0.4177 0.1108 0.0883 1.0000 Uiso R . . . . . H71 H 0.2077 0.3125 0.0805 0.0846 1.0000 Uiso R . . . . . H91 H 0.0190 0.4520 0.0314 0.0789 1.0000 Uiso R . . . . . H101 H 0.0826 0.5576 0.0613 0.0760 1.0000 Uiso R . . . . . H121 H 0.0254 0.2764 -0.0166 0.2212 1.0000 Uiso R . . . . . H122 H 0.0145 0.3649 -0.0121 0.2212 1.0000 Uiso R . . . . . H123 H 0.1163 0.3283 -0.0147 0.2212 1.0000 Uiso R . . . . . H131 H 0.0975 0.1876 0.0222 0.1558 1.0000 Uiso R . . . . . H132 H 0.1875 0.2392 0.0282 0.1558 1.0000 Uiso R . . . . . H133 H 0.1237 0.2153 0.0602 0.1558 1.0000 Uiso R . . . . . H141 H -0.0644 0.2429 0.0348 0.2147 1.0000 Uiso R . . . . . H142 H -0.0759 0.3284 0.0462 0.2147 1.0000 Uiso R . . . . . H143 H -0.0269 0.2698 0.0716 0.2147 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 0.0290(12) 0.110(3) 0.0645(17) -0.0014(17) 0.0000 0.0000 C2 0.0360(10) 0.0961(17) 0.0632(13) 0.0000(11) 0.0025(8) 0.0087(10) C3 0.0350(8) 0.0815(14) 0.0508(10) 0.0021(9) -0.0019(7) 0.0042(8) C4 0.0317(13) 0.0764(18) 0.0466(13) 0.0040(12) 0.0000 0.0000 C5 0.0426(9) 0.0715(12) 0.0513(10) 0.0013(9) 0.0010(7) 0.0083(9) C6 0.0561(12) 0.0853(16) 0.0664(13) 0.0032(12) -0.0121(10) 0.0207(11) C7 0.0689(15) 0.0718(15) 0.0783(15) 0.0040(12) -0.0099(12) 0.0219(11) C8 0.0589(12) 0.0658(14) 0.0687(13) 0.0043(10) -0.0044(10) 0.0045(10) C9 0.0526(11) 0.0669(13) 0.0644(13) 0.0045(10) -0.0107(9) 0.0041(9) C10 0.0471(10) 0.0623(12) 0.0568(11) 0.0041(9) -0.0033(8) 0.0061(8) C11 0.091(2) 0.0631(15) 0.118(2) -0.0034(14) -0.0261(18) 0.0037(13) C12 0.291(8) 0.089(2) 0.140(4) -0.013(2) -0.113(5) -0.011(3) C13 0.154(4) 0.084(2) 0.157(4) -0.028(2) -0.045(3) 0.026(2) C14 0.101(3) 0.113(3) 0.375(11) -0.055(4) 0.008(5) -0.040(3) Cl1 0.0304(4) 0.1538(11) 0.1114(8) -0.0103(7) 0.0000 0.0000 _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 10_565 1.373(3) yes C1 . C2 . 1.373(3) yes C1 . Cl1 . 1.737(3) yes C2 . C3 . 1.400(3) yes C2 . H21 . 0.950 no C3 . C4 . 1.411(2) yes C3 . C5 . 1.490(3) yes C4 . C4 27_554 1.501(5) yes C5 . C6 . 1.390(3) yes C5 . C10 . 1.390(3) yes C6 . C7 . 1.381(4) yes C6 . H61 . 0.950 no C7 . C8 . 1.384(3) yes C7 . H71 . 0.950 no C8 . C9 . 1.400(3) yes C8 . C11 . 1.524(4) yes C9 . C10 . 1.379(3) yes C9 . H91 . 0.950 no C10 . H101 . 0.950 no C11 . C12 . 1.471(6) yes C11 . C13 . 1.516(5) yes C11 . C14 . 1.544(6) yes C12 . H121 . 0.950 no C12 . H122 . 0.950 no C12 . H123 . 0.950 no C13 . H131 . 0.950 no C13 . H132 . 0.950 no C13 . H133 . 0.950 no C14 . H141 . 0.950 no C14 . H142 . 0.950 no C14 . H143 . 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 10_565 C1 . C2 . 121.3(3) yes C2 10_565 C1 . Cl1 . 119.37(13) yes C2 . C1 . Cl1 . 119.37(13) yes C1 . C2 . C3 . 120.3(2) yes C1 . C2 . H21 . 119.7 no C3 . C2 . H21 . 120.1 no C2 . C3 . C4 . 119.4(2) yes C2 . C3 . C5 . 116.65(19) yes C4 . C3 . C5 . 123.95(18) yes C4 27_554 C4 . C3 . 120.28(12) yes C4 27_554 C4 . C3 10_565 120.28(12) yes C3 . C4 . C3 10_565 119.4(2) yes C3 . C5 . C6 . 119.53(18) yes C3 . C5 . C10 . 123.17(19) yes C6 . C5 . C10 . 117.2(2) yes C5 . C6 . C7 . 121.4(2) yes C5 . C6 . H61 . 118.6 no C7 . C6 . H61 . 120.0 no C6 . C7 . C8 . 122.1(2) yes C6 . C7 . H71 . 119.5 no C8 . C7 . H71 . 118.4 no C7 . C8 . C9 . 116.2(2) yes C7 . C8 . C11 . 123.1(2) yes C9 . C8 . C11 . 120.8(2) yes C8 . C9 . C10 . 122.1(2) yes C8 . C9 . H91 . 118.2 no C10 . C9 . H91 . 119.6 no C5 . C10 . C9 . 120.99(19) yes C5 . C10 . H101 . 119.2 no C9 . C10 . H101 . 119.8 no C8 . C11 . C12 . 111.4(3) yes C8 . C11 . C13 . 113.0(3) yes C12 . C11 . C13 . 110.3(4) yes C8 . C11 . C14 . 107.8(3) yes C12 . C11 . C14 . 108.1(4) yes C13 . C11 . C14 . 106.0(4) yes C11 . C12 . H121 . 105.4 no C11 . C12 . H122 . 118.3 no H121 . C12 . H122 . 109.5 no C11 . C12 . H123 . 104.4 no H121 . C12 . H123 . 109.5 no H122 . C12 . H123 . 109.5 no C11 . C13 . H131 . 112.1 no C11 . C13 . H132 . 108.4 no H131 . C13 . H132 . 109.5 no C11 . C13 . H133 . 107.9 no H131 . C13 . H133 . 109.5 no H132 . C13 . H133 . 109.5 no C11 . C14 . H141 . 110.0 no C11 . C14 . H142 . 110.6 no H141 . C14 . H142 . 109.5 no C11 . C14 . H143 . 107.9 no H141 . C14 . H143 . 109.5 no H142 . C14 . H143 . 109.5 no