Electronic Supplementary Material for CrystEngComm This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 1350 _publ_requested_journal CrystEngComm loop_ _publ_author_name _publ_author_address _publ_author_footnote C.E.Housecroft ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Edwin C. Constable' ; ? # Address 2 ; ; ? # Footnote 2 ; 'Markus Neuburger' '' '' 'Sylvia Schaffner' '' '' 'Ellen J. Shardlow' '' '' _publ_contact_author_name 'Prof C E Housecroft' _publ_contact_author_address ; Departement Chemie University of Basel Spitalstrasse 51 Basel CH-4056 SWITZERLAND ; _publ_contact_author_email CATHERINE.HOUSECROFT@UNIBAS.CH _publ_section_title ; Polymorphs of 4'-(hex-5-ynyloxy)-2,2':6',2"-terpyridine: structural diversity arising from weak intermolecular interactions in the solid state ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_name_full ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_volume ? _journal_year ? _publ_contact_author_fax '+44 1865 285018' _publ_contact_author_phone '+44 1865 285024' # Check this file using the IUCr facility at: # http://journals.iucr.org/services/cif/checking/checkfull.html # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica C. The figures have been sent by mail. ; _publ_requested_category CO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' data_ejs44_173k _database_code_depnum_ccdc_archive 'CCDC 282120' _audit_creation_date 05-07-08 _audit_creation_method CRYSTALS_ver_12.24 _oxford_structure_analysis_title '7081046 ejs44_173k' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 5.6534(2) _cell_length_b 25.5246(9) _cell_length_c 12.1459(3) _cell_angle_alpha 90 _cell_angle_beta 94.310(2) _cell_angle_gamma 90 _cell_volume 1747.71(10) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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' 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' 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 4 _chemical_formula_sum 'C21 H19 N3 O1' _chemical_formula_moiety 'C21 H19 N3 O1' _chemical_compound_source ? _chemical_formula_weight 329.40 _cell_measurement_reflns_used 5341 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_temperature 173 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.07 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_max 0.34 _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 0.99 # Sheldrick geometric definitions 0.99 0.99 _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 'SIR92 (Altomare et al, 1994)' _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 173 _diffrn_reflns_number 12169 _reflns_number_total 3981 _diffrn_reflns_av_R_equivalents 0.025 # Number of reflections with Friedels Law is 3981 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4006 _diffrn_reflns_theta_min 1.861 _diffrn_reflns_theta_max 27.478 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.928 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 33 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _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 -0.17 _refine_diff_density_max 0.82 _refine_ls_number_reflns 2472 _refine_ls_number_restraints 0 _refine_ls_number_parameters 226 #_refine_ls_R_factor_ref 0.0595 _refine_ls_wR_factor_ref 0.0698 _refine_ls_goodness_of_fit_ref 0.9646 #_reflns_number_all 3956 _refine_ls_R_factor_all 0.0974 _refine_ls_wR_factor_all 0.2981 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.00u(I) _reflns_number_gt 2472 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_gt 0.0698 _refine_ls_shift/su_max 0.000250 # 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 ; p=P(6)*max(Fo^2^,0) + (1-P(6))Fc^2^ Method = SHELXL 97 (Sheldrick, 1997) W = 1. / [Sigma^2^(F*)+(P(1)p)^2^+P(2)p+P(4)+P(5)Sin(theta) ] P(i) are: 0.334E-01 0.119E-01 0.00 0.00 0.00 0.333 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, (1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Sheldrick, G.M. (1997). SHELXL-97. Program for the refinement of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 N1 N -0.2725(4) -0.34112(7) 0.73490(16) 0.0471 1.0000 Uani . . . . . . N2 N -0.0450(3) -0.21381(7) 0.81356(13) 0.0371 1.0000 Uani . . . . . . N3 N 0.3441(4) -0.11251(8) 0.92770(17) 0.0524 1.0000 Uani . . . . . . O1 O 0.4772(3) -0.30246(6) 0.98360(13) 0.0463 1.0000 Uani . . . . . . C1 C -0.4556(5) -0.36187(10) 0.67368(19) 0.0521 1.0000 Uani . . . . . . C2 C -0.6303(4) -0.33293(10) 0.61705(18) 0.0473 1.0000 Uani . . . . . . C3 C -0.6155(4) -0.27900(10) 0.62312(18) 0.0458 1.0000 Uani . . . . . . C4 C -0.4278(4) -0.25657(10) 0.68523(17) 0.0412 1.0000 Uani . . . . . . C5 C -0.2599(4) -0.28867(9) 0.74100(16) 0.0371 1.0000 Uani . . . . . . C6 C -0.0562(4) -0.26618(9) 0.81030(15) 0.0353 1.0000 Uani . . . . . . C7 C 0.1092(4) -0.29886(9) 0.86647(16) 0.0383 1.0000 Uani . . . . . . C8 C 0.3005(4) -0.27602(9) 0.92590(16) 0.0381 1.0000 Uani . . . . . . C9 C 0.3179(4) -0.22169(9) 0.92864(17) 0.0398 1.0000 Uani . . . . . . C10 C 0.1413(4) -0.19241(9) 0.87327(16) 0.0370 1.0000 Uani . . . . . . C11 C 0.1455(4) -0.13420(9) 0.87961(17) 0.0393 1.0000 Uani . . . . . . C12 C -0.0472(4) -0.10459(10) 0.84118(18) 0.0458 1.0000 Uani . . . . . . C13 C -0.0373(5) -0.05071(10) 0.8502(2) 0.0523 1.0000 Uani . . . . . . C14 C 0.1641(5) -0.02820(10) 0.8989(2) 0.0539 1.0000 Uani . . . . . . C15 C 0.3481(5) -0.06016(11) 0.9364(2) 0.0618 1.0000 Uani . . . . . . C16 C 0.4623(4) -0.35836(9) 0.98991(19) 0.0453 1.0000 Uani . . . . . . C17 C 0.6852(4) -0.37640(9) 1.05541(19) 0.0452 1.0000 Uani . . . . . . C18 C 0.6978(4) -0.43537(9) 1.07228(19) 0.0453 1.0000 Uani . . . . . . C19 C 0.9334(5) -0.45007(9) 1.1341(2) 0.0526 1.0000 Uani . . . . . . C20 C 0.9631(5) -0.50545(11) 1.16454(19) 0.0510 1.0000 Uani . . . . . . C21 C 0.9982(5) -0.54913(11) 1.1930(2) 0.0602 1.0000 Uani . . . . . . H11 H -0.4665 -0.4009 0.6689 0.0601 1.0000 Uiso R . . . . . H21 H -0.7638 -0.3505 0.5726 0.0552 1.0000 Uiso R . . . . . H31 H -0.7391 -0.2565 0.5833 0.0535 1.0000 Uiso R . . . . . H41 H -0.4127 -0.2176 0.6903 0.0482 1.0000 Uiso R . . . . . H71 H 0.0899 -0.3378 0.8640 0.0447 1.0000 Uiso R . . . . . H91 H 0.4556 -0.2041 0.9699 0.0467 1.0000 Uiso R . . . . . H121 H -0.1931 -0.1220 0.8068 0.0541 1.0000 Uiso R . . . . . H131 H -0.1741 -0.0285 0.8216 0.0611 1.0000 Uiso R . . . . . H141 H 0.1769 0.0107 0.9072 0.0643 1.0000 Uiso R . . . . . H151 H 0.4942 -0.0434 0.9721 0.0732 1.0000 Uiso R . . . . . H161 H 0.3191 -0.3689 1.0281 0.0531 1.0000 Uiso R . . . . . H162 H 0.4532 -0.3739 0.9141 0.0531 1.0000 Uiso R . . . . . H171 H 0.6928 -0.3591 1.1295 0.0534 1.0000 Uiso R . . . . . H172 H 0.8250 -0.3654 1.0152 0.0534 1.0000 Uiso R . . . . . H181 H 0.5644 -0.4467 1.1163 0.0530 1.0000 Uiso R . . . . . H182 H 0.6840 -0.4533 0.9989 0.0530 1.0000 Uiso R . . . . . H191 H 0.9502 -0.4290 1.2036 0.0625 1.0000 Uiso R . . . . . H192 H 1.0632 -0.4405 1.0862 0.0625 1.0000 Uiso R . . . . . H211 H 1.0288 -0.5862 1.2169 0.0700 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 N1 0.0448(13) 0.0391(13) 0.0550(12) -0.0021(9) -0.0114(10) -0.0010(9) N2 0.0349(11) 0.0365(11) 0.0390(9) 0.0004(8) -0.0038(8) -0.0003(8) N3 0.0423(13) 0.0401(13) 0.0728(14) -0.0069(10) -0.0091(10) -0.0001(10) O1 0.0414(10) 0.0366(10) 0.0578(9) 0.0070(7) -0.0157(7) -0.0015(8) C1 0.0537(17) 0.0396(15) 0.0609(15) -0.0082(12) -0.0104(13) -0.0045(13) C2 0.0420(15) 0.0511(16) 0.0470(13) -0.0064(11) -0.0081(11) -0.0050(12) C3 0.0388(14) 0.0511(16) 0.0456(12) 0.0023(11) -0.0100(10) 0.0022(12) C4 0.0376(14) 0.0414(14) 0.0433(12) 0.0017(10) -0.0051(10) 0.0006(10) C5 0.0360(13) 0.0385(14) 0.0364(11) -0.0007(10) -0.0002(9) -0.0003(10) C6 0.0331(13) 0.0384(14) 0.0339(11) 0.0012(9) -0.0006(9) -0.0014(10) C7 0.0394(13) 0.0359(13) 0.0390(11) 0.0037(10) -0.0016(10) -0.0019(11) C8 0.0351(13) 0.0397(14) 0.0382(11) 0.0049(10) -0.0043(10) 0.0030(11) C9 0.0356(13) 0.0407(14) 0.0419(12) 0.0010(10) -0.0057(10) -0.0029(11) C10 0.0347(13) 0.0391(13) 0.0369(11) -0.0007(10) -0.0003(10) 0.0002(10) C11 0.0386(14) 0.0393(14) 0.0397(12) -0.0008(10) 0.0005(10) -0.0008(11) C12 0.0422(15) 0.0410(14) 0.0525(13) -0.0006(11) -0.0079(11) 0.0005(11) C13 0.0524(17) 0.0420(16) 0.0609(15) -0.0020(12) -0.0052(12) 0.0069(12) C14 0.0561(17) 0.0370(14) 0.0679(16) -0.0033(13) -0.0005(13) 0.0019(14) C15 0.0489(18) 0.0446(16) 0.089(2) -0.0108(15) -0.0126(15) -0.0051(13) C16 0.0421(14) 0.0392(14) 0.0529(13) 0.0081(11) -0.0069(11) -0.0020(11) C17 0.0405(14) 0.0431(14) 0.0504(13) 0.0094(11) -0.0068(11) -0.0017(11) C18 0.0441(15) 0.0427(14) 0.0477(13) 0.0050(11) -0.0056(11) 0.0005(12) C19 0.0490(17) 0.0403(15) 0.0660(16) 0.0085(12) -0.0122(13) 0.0013(12) C20 0.0503(17) 0.0480(17) 0.0527(14) -0.0004(12) -0.0091(12) 0.0044(13) C21 0.071(2) 0.0410(16) 0.0651(16) -0.0026(13) -0.0179(14) 0.0076(14) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4043(12) 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 N1 . C1 . 1.338(3) yes N1 . C5 . 1.342(3) yes N2 . C6 . 1.339(3) yes N2 . C10 . 1.349(3) yes N3 . C11 . 1.345(3) yes N3 . C15 . 1.340(3) yes O1 . C8 . 1.356(2) yes O1 . C16 . 1.432(3) yes C1 . C2 . 1.375(3) yes C1 . H11 . 1.000 no C2 . C3 . 1.381(3) yes C2 . H21 . 1.000 no C3 . C4 . 1.379(3) yes C3 . H31 . 1.000 no C4 . C5 . 1.391(3) yes C4 . H41 . 1.000 no C5 . C6 . 1.489(3) yes C6 . C7 . 1.393(3) yes C7 . C8 . 1.383(3) yes C7 . H71 . 1.000 no C8 . C9 . 1.390(3) yes C9 . C10 . 1.381(3) yes C9 . H91 . 1.000 no C10 . C11 . 1.488(3) yes C11 . C12 . 1.378(3) yes C12 . C13 . 1.381(3) yes C12 . H121 . 1.000 no C13 . C14 . 1.369(4) yes C13 . H131 . 1.000 no C14 . C15 . 1.373(4) yes C14 . H141 . 1.000 no C15 . H151 . 1.000 no C16 . C17 . 1.510(3) yes C16 . H161 . 1.000 no C16 . H162 . 1.000 no C17 . C18 . 1.520(3) yes C17 . H171 . 1.000 no C17 . H172 . 1.000 no C18 . C19 . 1.526(3) yes C18 . H181 . 1.000 no C18 . H182 . 1.000 no C19 . C20 . 1.467(3) yes C19 . H191 . 1.000 no C19 . H192 . 1.000 no C20 . C21 . 1.180(3) yes C21 . H211 . 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 . N1 . C5 . 117.5(2) yes C6 . N2 . C10 . 116.99(18) yes C11 . N3 . C15 . 116.9(2) yes C8 . O1 . C16 . 118.67(17) yes N1 . C1 . C2 . 124.2(2) yes N1 . C1 . H11 . 117.915 no C2 . C1 . H11 . 117.898 no C1 . C2 . C3 . 118.1(2) yes C1 . C2 . H21 . 120.948 no C3 . C2 . H21 . 120.986 no C2 . C3 . C4 . 119.0(2) yes C2 . C3 . H31 . 120.557 no C4 . C3 . H31 . 120.492 no C3 . C4 . C5 . 119.4(2) yes C3 . C4 . H41 . 120.375 no C5 . C4 . H41 . 120.241 no C4 . C5 . N1 . 122.0(2) yes C4 . C5 . C6 . 121.2(2) yes N1 . C5 . C6 . 116.80(19) yes C5 . C6 . N2 . 115.76(18) yes C5 . C6 . C7 . 120.5(2) yes N2 . C6 . C7 . 123.7(2) yes C6 . C7 . C8 . 118.2(2) yes C6 . C7 . H71 . 120.865 no C8 . C7 . H71 . 120.913 no C7 . C8 . O1 . 125.2(2) yes C7 . C8 . C9 . 119.0(2) yes O1 . C8 . C9 . 115.85(19) yes C8 . C9 . C10 . 118.8(2) yes C8 . C9 . H91 . 120.633 no C10 . C9 . H91 . 120.615 no C9 . C10 . N2 . 123.3(2) yes C9 . C10 . C11 . 120.5(2) yes N2 . C10 . C11 . 116.16(19) yes C10 . C11 . N3 . 116.3(2) yes C10 . C11 . C12 . 121.4(2) yes N3 . C11 . C12 . 122.3(2) yes C11 . C12 . C13 . 119.5(2) yes C11 . C12 . H121 . 120.275 no C13 . C12 . H121 . 120.177 no C12 . C13 . C14 . 118.7(2) yes C12 . C13 . H131 . 120.766 no C14 . C13 . H131 . 120.559 no C13 . C14 . C15 . 118.6(3) yes C13 . C14 . H141 . 120.787 no C15 . C14 . H141 . 120.624 no C14 . C15 . N3 . 124.0(2) yes C14 . C15 . H151 . 118.033 no N3 . C15 . H151 . 118.002 no O1 . C16 . C17 . 106.38(19) yes O1 . C16 . H161 . 110.239 no C17 . C16 . H161 . 110.233 no O1 . C16 . H162 . 110.192 no C17 . C16 . H162 . 110.295 no H161 . C16 . H162 . 109.467 no C16 . C17 . C18 . 113.70(19) yes C16 . C17 . H171 . 108.474 no C18 . C17 . H171 . 108.531 no C16 . C17 . H172 . 108.409 no C18 . C17 . H172 . 108.211 no H171 . C17 . H172 . 109.467 no C17 . C18 . C19 . 109.91(19) yes C17 . C18 . H181 . 109.166 no C19 . C18 . H181 . 109.363 no C17 . C18 . H182 . 109.484 no C19 . C18 . H182 . 109.440 no H181 . C18 . H182 . 109.467 no C18 . C19 . C20 . 116.1(2) yes C18 . C19 . H191 . 107.875 no C20 . C19 . H191 . 107.675 no C18 . C19 . H192 . 107.786 no C20 . C19 . H192 . 107.816 no H191 . C19 . H192 . 109.467 no C19 . C20 . C21 . 176.1(3) yes C20 . C21 . H211 . 179.692 no data_ejs44_2 _database_code_depnum_ccdc_archive 'CCDC 282121' _audit_creation_date 05-08-11 _audit_creation_method CRYSTALS_ver_12.24 _oxford_structure_analysis_title '8111315 ejs44_2_173k' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 35.6129(12) _cell_length_b 5.4646(2) _cell_length_c 20.5952(7) _cell_angle_alpha 90 _cell_angle_beta 120.439(2) _cell_angle_gamma 90 _cell_volume 3455.6(2) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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' 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' 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 8 _chemical_formula_sum 'C21 H19 N3 O1' _chemical_formula_moiety 'C21 H19 N3 O1' _chemical_compound_source ? _chemical_formula_weight 329.40 _cell_measurement_reflns_used 9015 _cell_measurement_theta_min 1 _cell_measurement_theta_max 30 _cell_measurement_temperature 173 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_min 0.04 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_max 0.54 _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Denzo/Scalepack (Otwinowski & Minor, 1996)' _exptl_absorpt_correction_T_min 0.99 _exptl_absorpt_correction_T_max 1.00 # Sheldrick geometric definitions 0.99 1.00 _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 ; EvalCCD A. J. M. Duisenberg. Reflections on Area Detectors. Thesis, Utrecht, 1998 ; _computing_cell_refinement ; EvalCCD A. J. M. Duisenberg. Reflections on Area Detectors. Thesis, Utrecht, 1998 ; _computing_structure_solution 'SIR97 (Altomare et al, 1999)' _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 173 _diffrn_reflns_number 48465 _reflns_number_total 5038 _diffrn_reflns_av_R_equivalents 0.069 # Number of reflections with Friedels Law is 5038 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 5044 _diffrn_reflns_theta_min 3.180 _diffrn_reflns_theta_max 30.009 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 30.009 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -49 _diffrn_reflns_limit_h_max 50 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _reflns_limit_h_min -50 _reflns_limit_h_max 42 _reflns_limit_k_min 0 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 28 _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 -0.22 _refine_diff_density_max 1.02 _refine_ls_number_reflns 2605 _refine_ls_number_restraints 0 _refine_ls_number_parameters 226 #_refine_ls_R_factor_ref 0.0504 _refine_ls_wR_factor_ref 0.0326 _refine_ls_goodness_of_fit_ref 1.2421 #_reflns_number_all 5013 _refine_ls_R_factor_all 0.1034 _refine_ls_wR_factor_all 0.0443 # 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 2605 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_gt 0.0326 _refine_ls_shift/su_max 0.000548 # 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: 2.48 -2.38 1.37 ; _publ_section_abstract # Text of the abstract ; ? ; _publ_section_comment # Text of the paper ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen ; H atoms placed geometrically after each cycle ; _publ_section_exptl_prep ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Grazia, A., Moliterni, G., Polidori, G. and Spagna, R. (1999) SIR97: a new tool for crystal structure determination and refinement.J. App. Cryst. 32, 115-119 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, (1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 0.34969(4) -0.0792(2) 0.48761(6) 0.0320 1.0000 Uani . . . . . . N1 N 0.36973(4) 0.0373(3) 0.74908(8) 0.0292 1.0000 Uani . . . . . . N2 N 0.41914(4) 0.3906(3) 0.66612(7) 0.0238 1.0000 Uani . . . . . . N3 N 0.46299(4) 0.5615(3) 0.54973(7) 0.0278 1.0000 Uani . . . . . . C1 C 0.36793(6) 0.0351(4) 0.81242(10) 0.0323 1.0000 Uani . . . . . . C2 C 0.38655(5) 0.2089(4) 0.86773(9) 0.0323 1.0000 Uani . . . . . . C3 C 0.40826(5) 0.4005(4) 0.85771(9) 0.0294 1.0000 Uani . . . . . . C4 C 0.41084(5) 0.4082(3) 0.79297(9) 0.0256 1.0000 Uani . . . . . . C5 C 0.39105(5) 0.2238(3) 0.74016(8) 0.0237 1.0000 Uani . . . . . . C6 C 0.39287(5) 0.2249(3) 0.66955(8) 0.0228 1.0000 Uani . . . . . . C7 C 0.36781(5) 0.0620(3) 0.61176(9) 0.0260 1.0000 Uani . . . . . . C8 C 0.37159(5) 0.0696(3) 0.54795(8) 0.0248 1.0000 Uani . . . . . . C9 C 0.39933(5) 0.2381(3) 0.54380(8) 0.0245 1.0000 Uani . . . . . . C10 C 0.42231(5) 0.3946(3) 0.60373(8) 0.0222 1.0000 Uani . . . . . . C11 C 0.45227(5) 0.5817(3) 0.60331(8) 0.0223 1.0000 Uani . . . . . . C12 C 0.46809(5) 0.7673(3) 0.65650(9) 0.0271 1.0000 Uani . . . . . . C13 C 0.49637(5) 0.9369(3) 0.65562(9) 0.0295 1.0000 Uani . . . . . . C14 C 0.50811(5) 0.9162(4) 0.60153(9) 0.0301 1.0000 Uani . . . . . . C15 C 0.49054(5) 0.7281(4) 0.55034(9) 0.0318 1.0000 Uani . . . . . . C16 C 0.32056(5) -0.2574(4) 0.48884(9) 0.0302 1.0000 Uani . . . . . . C17 C 0.30369(5) -0.4058(3) 0.41792(10) 0.0310 1.0000 Uani . . . . . . C18 C 0.27043(6) -0.5949(4) 0.40968(10) 0.0323 1.0000 Uani . . . . . . C19 C 0.25442(7) -0.7413(4) 0.33749(11) 0.0430 1.0000 Uani . . . . . . C20 C 0.22306(6) -0.9326(4) 0.32678(11) 0.0393 1.0000 Uani . . . . . . C21 C 0.19775(6) -1.0843(4) 0.31788(11) 0.0424 1.0000 Uani . . . . . . H11 H 0.3519 -0.1025 0.8196 0.0415 1.0000 Uiso R . . . . . H21 H 0.3843 0.1978 0.9141 0.0404 1.0000 Uiso R . . . . . H31 H 0.4222 0.5311 0.8968 0.0360 1.0000 Uiso R . . . . . H41 H 0.4263 0.5449 0.7840 0.0307 1.0000 Uiso R . . . . . H71 H 0.3478 -0.0568 0.6160 0.0298 1.0000 Uiso R . . . . . H91 H 0.4028 0.2453 0.4986 0.0275 1.0000 Uiso R . . . . . H121 H 0.4589 0.7773 0.6949 0.0308 1.0000 Uiso R . . . . . H131 H 0.5082 1.0722 0.6935 0.0331 1.0000 Uiso R . . . . . H141 H 0.5289 1.0343 0.5995 0.0354 1.0000 Uiso R . . . . . H151 H 0.4988 0.7144 0.5108 0.0380 1.0000 Uiso R . . . . . H161 H 0.3363 -0.3658 0.5339 0.0358 1.0000 Uiso R . . . . . H162 H 0.2958 -0.1749 0.4899 0.0358 1.0000 Uiso R . . . . . H171 H 0.3288 -0.4917 0.4189 0.0351 1.0000 Uiso R . . . . . H172 H 0.2899 -0.2924 0.3738 0.0351 1.0000 Uiso R . . . . . H181 H 0.2840 -0.7085 0.4538 0.0369 1.0000 Uiso R . . . . . H182 H 0.2450 -0.5101 0.4078 0.0369 1.0000 Uiso R . . . . . H191 H 0.2802 -0.8214 0.3394 0.0520 1.0000 Uiso R . . . . . H192 H 0.2406 -0.6263 0.2937 0.0520 1.0000 Uiso R . . . . . H211 H 0.1761 -1.2140 0.3105 0.0448 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 0.0334(6) 0.0368(7) 0.0287(6) -0.0132(6) 0.0178(5) -0.0158(6) N1 0.0341(8) 0.0283(8) 0.0308(7) -0.0008(6) 0.0205(6) -0.0037(7) N2 0.0245(6) 0.0258(8) 0.0222(6) -0.0005(6) 0.0126(5) -0.0032(6) N3 0.0325(7) 0.0304(8) 0.0228(6) 0.0005(6) 0.0158(6) -0.0054(7) C1 0.0335(9) 0.0351(11) 0.0373(9) 0.0052(8) 0.0245(8) -0.0031(8) C2 0.0349(9) 0.0420(11) 0.0277(8) 0.0048(8) 0.0215(7) 0.0068(9) C3 0.0311(8) 0.0349(10) 0.0245(7) -0.0026(8) 0.0158(7) 0.0024(8) C4 0.0265(8) 0.0265(9) 0.0259(7) -0.0004(7) 0.0148(6) -0.0009(7) C5 0.0226(7) 0.0262(9) 0.0240(7) 0.0018(7) 0.0132(6) 0.0012(7) C6 0.0230(7) 0.0238(9) 0.0233(7) 0.0008(7) 0.0130(6) 0.0006(7) C7 0.0248(7) 0.0286(9) 0.0272(7) -0.0037(8) 0.0150(6) -0.0073(8) C8 0.0239(7) 0.0257(9) 0.0245(8) -0.0053(7) 0.0120(6) -0.0030(7) C9 0.0238(7) 0.0295(9) 0.0211(7) -0.0021(7) 0.0120(6) -0.0031(7) C10 0.0213(7) 0.0221(9) 0.0222(7) 0.0010(7) 0.0103(6) -0.0013(7) C11 0.0193(7) 0.0253(8) 0.0189(7) 0.0051(7) 0.0073(6) 0.0006(7) C12 0.0268(8) 0.0298(9) 0.0249(7) -0.0002(8) 0.0132(6) -0.0041(8) C13 0.0276(8) 0.0265(9) 0.0280(8) 0.0001(8) 0.0094(7) -0.0034(8) C14 0.0276(8) 0.0298(10) 0.0306(8) 0.0081(8) 0.0130(7) -0.0060(8) C15 0.0352(9) 0.0358(10) 0.0297(8) 0.0049(8) 0.0204(7) -0.0032(9) C16 0.0291(8) 0.0294(10) 0.0339(8) -0.0068(8) 0.0172(7) -0.0093(8) C17 0.0293(8) 0.0266(9) 0.0333(8) -0.0062(8) 0.0129(7) -0.0059(8) C18 0.0292(8) 0.0277(10) 0.0366(9) -0.0041(9) 0.0141(7) -0.0070(8) C19 0.0442(10) 0.0380(12) 0.0442(10) -0.0130(10) 0.0206(9) -0.0182(10) C20 0.0327(9) 0.0335(10) 0.0407(10) -0.0045(9) 0.0106(8) -0.0030(9) C21 0.0332(9) 0.0309(10) 0.0485(11) -0.0014(10) 0.0100(8) -0.0056(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.9713(13) 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 . C8 . 1.3532(19) yes O1 . C16 . 1.433(2) yes N1 . C1 . 1.338(2) yes N1 . C5 . 1.338(2) yes N2 . C6 . 1.329(2) yes N2 . C10 . 1.346(2) yes N3 . C11 . 1.343(2) yes N3 . C15 . 1.334(2) yes C1 . C2 . 1.369(3) yes C1 . H11 . 1.000 no C2 . C3 . 1.378(3) yes C2 . H21 . 1.000 no C3 . C4 . 1.383(2) yes C3 . H31 . 1.000 no C4 . C5 . 1.385(2) yes C4 . H41 . 1.000 no C5 . C6 . 1.488(2) yes C6 . C7 . 1.389(2) yes C7 . C8 . 1.388(2) yes C7 . H71 . 1.000 no C8 . C9 . 1.384(2) yes C9 . C10 . 1.379(2) yes C9 . H91 . 1.000 no C10 . C11 . 1.481(2) yes C11 . C12 . 1.386(2) yes C12 . C13 . 1.376(2) yes C12 . H121 . 1.000 no C13 . C14 . 1.379(2) yes C13 . H131 . 1.000 no C14 . C15 . 1.375(3) yes C14 . H141 . 1.000 no C15 . H151 . 1.000 no C16 . C17 . 1.504(2) yes C16 . H161 . 1.000 no C16 . H162 . 1.000 no C17 . C18 . 1.515(2) yes C17 . H171 . 1.000 no C17 . H172 . 1.000 no C18 . C19 . 1.522(3) yes C18 . H181 . 1.000 no C18 . H182 . 1.000 no C19 . C20 . 1.462(3) yes C19 . H191 . 1.000 no C19 . H192 . 1.000 no C20 . C21 . 1.169(3) yes C21 . H211 . 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 C8 . O1 . C16 . 118.54(13) yes C1 . N1 . C5 . 116.84(16) yes C6 . N2 . C10 . 117.61(14) yes C11 . N3 . C15 . 116.75(16) yes N1 . C1 . C2 . 124.24(17) yes N1 . C1 . H11 . 117.691 no C2 . C1 . H11 . 118.066 no C1 . C2 . C3 . 118.34(15) yes C1 . C2 . H21 . 120.923 no C3 . C2 . H21 . 120.741 no C2 . C3 . C4 . 118.96(17) yes C2 . C3 . H31 . 120.571 no C4 . C3 . H31 . 120.463 no C3 . C4 . C5 . 118.61(17) yes C3 . C4 . H41 . 120.916 no C5 . C4 . H41 . 120.468 no C4 . C5 . N1 . 123.00(14) yes C4 . C5 . C6 . 120.52(15) yes N1 . C5 . C6 . 116.48(15) yes C5 . C6 . N2 . 115.77(15) yes C5 . C6 . C7 . 120.52(15) yes N2 . C6 . C7 . 123.71(15) yes C6 . C7 . C8 . 117.63(15) yes C6 . C7 . H71 . 121.232 no C8 . C7 . H71 . 121.134 no C7 . C8 . O1 . 124.35(16) yes C7 . C8 . C9 . 119.53(15) yes O1 . C8 . C9 . 116.11(14) yes C8 . C9 . C10 . 118.41(15) yes C8 . C9 . H91 . 120.820 no C10 . C9 . H91 . 120.765 no C9 . C10 . N2 . 123.08(15) yes C9 . C10 . C11 . 121.72(14) yes N2 . C10 . C11 . 115.20(14) yes C10 . C11 . N3 . 116.97(15) yes C10 . C11 . C12 . 120.41(14) yes N3 . C11 . C12 . 122.62(16) yes C11 . C12 . C13 . 119.32(16) yes C11 . C12 . H121 . 120.030 no C13 . C12 . H121 . 120.650 no C12 . C13 . C14 . 118.63(18) yes C12 . C13 . H131 . 120.649 no C14 . C13 . H131 . 120.725 no C13 . C14 . C15 . 118.32(17) yes C13 . C14 . H141 . 121.073 no C15 . C14 . H141 . 120.602 no C14 . C15 . N3 . 124.35(16) yes C14 . C15 . H151 . 118.231 no N3 . C15 . H151 . 117.421 no O1 . C16 . C17 . 106.62(14) yes O1 . C16 . H161 . 110.376 no C17 . C16 . H161 . 110.048 no O1 . C16 . H162 . 110.352 no C17 . C16 . H162 . 109.945 no H161 . C16 . H162 . 109.467 no C16 . C17 . C18 . 112.43(15) yes C16 . C17 . H171 . 108.630 no C18 . C17 . H171 . 108.774 no C16 . C17 . H172 . 108.610 no C18 . C17 . H172 . 108.900 no H171 . C17 . H172 . 109.467 no C17 . C18 . C19 . 110.65(15) yes C17 . C18 . H181 . 109.345 no C19 . C18 . H181 . 109.319 no C17 . C18 . H182 . 109.235 no C19 . C18 . H182 . 108.806 no H181 . C18 . H182 . 109.467 no C18 . C19 . C20 . 113.74(17) yes C18 . C19 . H191 . 108.069 no C20 . C19 . H191 . 108.028 no C18 . C19 . H192 . 108.629 no C20 . C19 . H192 . 108.845 no H191 . C19 . H192 . 109.467 no C19 . C20 . C21 . 179.5(2) yes C20 . C21 . H211 . 179.749 no