data_global #=========================================================================== _audit_creation_date '2011-11-01' _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _audit_update_record ; ; #=========================================================================== # 1. SUBMISSION DETAILS #=========================================================================== _publ_contact_author_name 'Dr Damon A. Parrish' _publ_contact_author_address ; Laboratory for the Structure of Matter Naval Research Laboratory Washington, DC 20375 ; _publ_contact_author_email 'damon.parrish@nrl.navy.mil' _publ_contact_author_fax '202-767-6874' _publ_contact_author_phone '202-404-2141' _publ_requested_journal ? _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter ; ; #=========================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) # Do NOT alter anthing in this section. #=========================================================================== _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 ? #=========================================================================== # 3. TITLE AND AUTHOR LIST #=========================================================================== _publ_section_title ; title ; loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Parrish, Damon A.' ; Laboratory for the Structure of Matter, Code 6910 Naval Research Laboratory Washington, DC 20375 ; ? 'Lakshman, Mahesh' ; Department of Chemistry The City College and The City University of New York 160 Convent Avenue New York, NY 10031 ; ? #=========================================================================== # 4. TEXT #=========================================================================== _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_references ; Bruker (2009). PROTEUM v2009.7-0. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2009). SAINT v7.66A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2008). SADABS v2008/1, Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2008). XPREP v2008/2. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2008). SHELXTL v2008/4. Bruker AXS Inc., Madison, Wisconsin, USA. ; _publ_section_figure_captions ; ; _publ_section_table_legends ; ; _publ_section_acknowledgements ; Crystallographic studies were supported in part by the Office of Naval Research (ONR) and the Naval Research Laboratory (NRL). ; #========================================================================== data_lak016 _audit_creation_date '2011-11-01' _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; 5-methylbenzo[c]phenanthrene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H14' _chemical_formula_sum 'C19 H14' _chemical_formula_weight 242.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 5.8248(2) _cell_length_b 14.0599(4) _cell_length_c 14.9651(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1225.58(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.560 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.9058 _exptl_absorpt_correction_T_max 0.9358 _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_type 'CuK\a' _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'Helios optics' _diffrn_measurement_device 'Bruker PLATINUM 135 CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6718 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.31 _diffrn_reflns_theta_max 68.48 _reflns_number_total 2103 _reflns_number_gt 2079 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker PROTEUM v2009.7-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker PROTEUM v2009.7-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.66A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_structure_refinement 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_molecular_graphics 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+0.1962P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0045(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(16) _refine_ls_number_reflns 2103 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0766 _refine_ls_wR_factor_gt 0.0762 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2779(2) 0.62221(9) 1.07990(8) 0.0201(3) Uani 1 1 d . . . C2 C 0.0967(2) 0.58209(8) 1.12257(8) 0.0205(3) Uani 1 1 d . . . H2 H 0.0718 0.5972 1.1823 0.025 Uiso 1 1 calc R . . C3 C -0.0574(2) 0.51766(9) 1.07971(8) 0.0200(3) Uani 1 1 d . . . C4 C -0.2450(2) 0.47956(9) 1.12955(8) 0.0228(3) Uani 1 1 d . . . H4 H -0.2594 0.4946 1.1898 0.027 Uiso 1 1 calc R . . C5 C -0.4021(2) 0.42204(9) 1.09085(9) 0.0229(3) Uani 1 1 d . . . H5 H -0.5312 0.4034 1.1229 0.028 Uiso 1 1 calc R . . C6 C -0.3715(2) 0.38974(8) 1.00127(8) 0.0205(3) Uani 1 1 d . . . C7 C -0.5270(2) 0.32417(9) 0.96328(9) 0.0231(3) Uani 1 1 d . . . H7 H -0.6599 0.3084 0.9943 0.028 Uiso 1 1 calc R . . C8 C -0.4867(2) 0.28328(9) 0.88186(9) 0.0241(3) Uani 1 1 d . . . H8 H -0.5935 0.2422 0.8565 0.029 Uiso 1 1 calc R . . C9 C -0.2808(2) 0.30455(9) 0.83725(8) 0.0235(3) Uani 1 1 d . . . H9 H -0.2468 0.2739 0.7838 0.028 Uiso 1 1 calc R . . C10 C -0.1293(2) 0.36966(8) 0.87127(8) 0.0207(3) Uani 1 1 d . . . H10 H 0.0068 0.3815 0.8407 0.025 Uiso 1 1 calc R . . C11 C -0.1746(2) 0.41957(8) 0.95201(8) 0.0188(3) Uani 1 1 d . . . C12 C -0.0282(2) 0.49334(8) 0.98904(8) 0.0189(3) Uani 1 1 d . . . C13 C 0.1460(2) 0.54527(8) 0.93907(8) 0.0181(3) Uani 1 1 d . . . C14 C 0.1589(2) 0.54553(8) 0.84452(8) 0.0202(3) Uani 1 1 d . . . H14 H 0.0458 0.5143 0.8119 0.024 Uiso 1 1 calc R . . C15 C 0.3331(2) 0.59051(8) 0.79959(8) 0.0223(3) Uani 1 1 d . . . H15 H 0.3383 0.5881 0.7375 0.027 Uiso 1 1 calc R . . C16 C 0.5027(2) 0.63995(9) 0.84647(8) 0.0245(3) Uani 1 1 d . . . H16 H 0.6264 0.6667 0.8163 0.029 Uiso 1 1 calc R . . C17 C 0.4846(2) 0.64852(8) 0.93746(8) 0.0223(3) Uani 1 1 d . . . H17 H 0.5934 0.6842 0.9682 0.027 Uiso 1 1 calc R . . C18 C 0.3053(2) 0.60461(8) 0.98573(8) 0.0188(3) Uani 1 1 d . . . C19 C 0.4425(2) 0.68630(9) 1.12866(8) 0.0234(3) Uani 1 1 d . . . H19A H 0.3979 0.6908 1.1903 0.035 Uiso 1 1 calc R . . H19B H 0.4397 0.7484 1.1021 0.035 Uiso 1 1 calc R . . H19C H 0.5948 0.6606 1.1247 0.035 Uiso 1 1 calc 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 0.0231(6) 0.0156(5) 0.0216(6) -0.0008(5) -0.0030(5) 0.0059(5) C2 0.0257(7) 0.0183(6) 0.0177(6) -0.0011(4) -0.0006(5) 0.0061(5) C3 0.0214(7) 0.0172(5) 0.0213(6) 0.0023(5) 0.0004(5) 0.0052(5) C4 0.0265(7) 0.0215(6) 0.0205(6) 0.0008(5) 0.0039(5) 0.0053(5) C5 0.0202(6) 0.0208(6) 0.0278(6) 0.0049(5) 0.0058(5) 0.0038(5) C6 0.0198(6) 0.0163(5) 0.0254(6) 0.0040(5) -0.0002(5) 0.0036(5) C7 0.0172(6) 0.0211(6) 0.0309(6) 0.0066(5) 0.0001(6) 0.0006(5) C8 0.0235(7) 0.0207(6) 0.0281(6) 0.0027(5) -0.0048(5) -0.0052(5) C9 0.0287(7) 0.0207(6) 0.0212(6) 0.0003(5) -0.0008(5) -0.0025(5) C10 0.0218(6) 0.0191(6) 0.0212(6) 0.0028(5) 0.0012(5) -0.0013(5) C11 0.0181(6) 0.0170(5) 0.0211(6) 0.0041(4) -0.0014(5) 0.0021(5) C12 0.0181(6) 0.0159(5) 0.0227(6) 0.0016(5) -0.0012(5) 0.0038(5) C13 0.0181(6) 0.0141(5) 0.0220(6) 0.0009(4) -0.0011(5) 0.0022(5) C14 0.0220(6) 0.0157(5) 0.0228(6) -0.0001(4) -0.0033(5) -0.0014(5) C15 0.0287(7) 0.0195(6) 0.0186(6) 0.0005(4) 0.0000(5) 0.0001(6) C16 0.0250(7) 0.0218(6) 0.0266(6) 0.0029(5) 0.0023(5) -0.0049(6) C17 0.0221(7) 0.0189(6) 0.0260(6) -0.0012(5) -0.0039(5) -0.0032(5) C18 0.0197(6) 0.0148(6) 0.0219(6) 0.0013(5) -0.0026(5) 0.0028(5) C19 0.0255(6) 0.0215(6) 0.0230(6) -0.0027(5) -0.0032(5) 0.0036(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3565(18) . ? C1 C18 1.4397(17) . ? C1 C19 1.5043(18) . ? C2 C3 1.4276(18) . ? C2 H2 0.9300 . ? C3 C12 1.4095(16) . ? C3 C4 1.4271(18) . ? C4 C5 1.3516(19) . ? C4 H4 0.9300 . ? C5 C6 1.4267(18) . ? C5 H5 0.9300 . ? C6 C7 1.4118(17) . ? C6 C11 1.4263(17) . ? C7 C8 1.3676(19) . ? C7 H7 0.9300 . ? C8 C9 1.4045(18) . ? C8 H8 0.9300 . ? C9 C10 1.3696(17) . ? C9 H9 0.9300 . ? C10 C11 1.4220(17) . ? C10 H10 0.9300 . ? C11 C12 1.4526(17) . ? C12 C13 1.4568(17) . ? C13 C14 1.4169(16) . ? C13 C18 1.4298(16) . ? C14 C15 1.3716(18) . ? C14 H14 0.9300 . ? C15 C16 1.3972(18) . ? C15 H15 0.9300 . ? C16 C17 1.3710(17) . ? C16 H16 0.9300 . ? C17 C18 1.4122(18) . ? C17 H17 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C18 118.39(12) . . ? C2 C1 C19 121.10(11) . . ? C18 C1 C19 120.48(11) . . ? C1 C2 C3 122.80(11) . . ? C1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C12 C3 C4 120.30(12) . . ? C12 C3 C2 120.70(11) . . ? C4 C3 C2 119.00(11) . . ? C5 C4 C3 121.26(11) . . ? C5 C4 H4 119.4 . . ? C3 C4 H4 119.4 . . ? C4 C5 C6 120.56(12) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C11 119.97(11) . . ? C7 C6 C5 120.41(11) . . ? C11 C6 C5 119.51(11) . . ? C8 C7 C6 121.55(12) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C7 C8 C9 118.72(12) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? C10 C9 C8 121.04(11) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 121.75(12) . . ? C9 C10 H10 119.1 . . ? C11 C10 H10 119.1 . . ? C10 C11 C6 116.30(11) . . ? C10 C11 C12 124.59(11) . . ? C6 C11 C12 119.00(11) . . ? C3 C12 C11 118.01(11) . . ? C3 C12 C13 117.18(11) . . ? C11 C12 C13 124.81(10) . . ? C14 C13 C18 116.86(11) . . ? C14 C13 C12 123.43(11) . . ? C18 C13 C12 119.58(10) . . ? C15 C14 C13 122.00(11) . . ? C15 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C14 C15 C16 120.42(11) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C17 C16 C15 119.22(12) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C16 C17 C18 121.76(12) . . ? C16 C17 H17 119.1 . . ? C18 C17 H17 119.1 . . ? C17 C18 C13 119.03(10) . . ? C17 C18 C1 120.49(11) . . ? C13 C18 C1 120.43(11) . . ? C1 C19 H19A 109.5 . . ? C1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C18 C1 C2 C3 4.85(17) . . . . ? C19 C1 C2 C3 -177.19(11) . . . . ? C1 C2 C3 C12 -0.66(18) . . . . ? C1 C2 C3 C4 -179.38(10) . . . . ? C12 C3 C4 C5 -2.05(18) . . . . ? C2 C3 C4 C5 176.68(11) . . . . ? C3 C4 C5 C6 6.61(18) . . . . ? C4 C5 C6 C7 175.34(11) . . . . ? C4 C5 C6 C11 -0.80(17) . . . . ? C11 C6 C7 C8 4.20(18) . . . . ? C5 C6 C7 C8 -171.92(11) . . . . ? C6 C7 C8 C9 2.63(18) . . . . ? C7 C8 C9 C10 -4.27(18) . . . . ? C8 C9 C10 C11 -1.02(19) . . . . ? C9 C10 C11 C6 7.58(17) . . . . ? C9 C10 C11 C12 -176.25(11) . . . . ? C7 C6 C11 C10 -9.05(16) . . . . ? C5 C6 C11 C10 167.11(11) . . . . ? C7 C6 C11 C12 174.56(10) . . . . ? C5 C6 C11 C12 -9.29(16) . . . . ? C4 C3 C12 C11 -8.02(16) . . . . ? C2 C3 C12 C11 173.28(11) . . . . ? C4 C3 C12 C13 171.29(11) . . . . ? C2 C3 C12 C13 -7.41(16) . . . . ? C10 C11 C12 C3 -162.58(11) . . . . ? C6 C11 C12 C3 13.50(16) . . . . ? C10 C11 C12 C13 18.17(18) . . . . ? C6 C11 C12 C13 -165.75(10) . . . . ? C3 C12 C13 C14 -164.48(11) . . . . ? C11 C12 C13 C14 14.78(18) . . . . ? C3 C12 C13 C18 11.24(15) . . . . ? C11 C12 C13 C18 -169.50(10) . . . . ? C18 C13 C14 C15 8.13(17) . . . . ? C12 C13 C14 C15 -176.04(11) . . . . ? C13 C14 C15 C16 -1.46(19) . . . . ? C14 C15 C16 C17 -4.4(2) . . . . ? C15 C16 C17 C18 3.3(2) . . . . ? C16 C17 C18 C13 3.61(18) . . . . ? C16 C17 C18 C1 -174.03(12) . . . . ? C14 C13 C18 C17 -9.04(16) . . . . ? C12 C13 C18 C17 174.96(10) . . . . ? C14 C13 C18 C1 168.61(11) . . . . ? C12 C13 C18 C1 -7.39(16) . . . . ? C2 C1 C18 C17 176.89(11) . . . . ? C19 C1 C18 C17 -1.08(17) . . . . ? C2 C1 C18 C13 -0.72(16) . . . . ? C19 C1 C18 C13 -178.69(10) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 68.48 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.143 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.036