# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_rm106 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H13 B F2 N2' _chemical_formula_weight 342.14 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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.5995(2) _cell_length_b 13.5098(4) _cell_length_c 22.2683(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1684.56(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5140 _cell_measurement_theta_min 3.2686 _cell_measurement_theta_max 71.9563 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.779 _exptl_absorpt_correction_T_min 0.8535 _exptl_absorpt_correction_T_max 0.9055 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Micro-Focus (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION SUPER NOVA' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11102 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_unetI/netI 0.0157 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.83 _diffrn_reflns_theta_max 72.10 _reflns_number_total 3269 _reflns_number_gt 2882 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0434P)^2^+0.0493P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0027(3) _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 0.10(14) _refine_ls_number_reflns 3269 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0336 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0788 _refine_ls_wR_factor_gt 0.0735 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 F1 F 0.6083(2) 0.98169(6) 0.83188(5) 0.0868(3) Uani 1 1 d . . . F2 F 0.85293(18) 1.10113(8) 0.86720(4) 0.0846(3) Uani 1 1 d . . . N1 N 0.9051(2) 1.04612(8) 0.76515(5) 0.0570(3) Uani 1 1 d . . . N2 N 0.5574(2) 1.14705(8) 0.79440(5) 0.0593(3) Uani 1 1 d . . . C5 C 0.7674(3) 1.17897(10) 0.70151(6) 0.0590(3) Uani 1 1 d . . . C15 C 0.9448(3) 1.50688(11) 0.47164(6) 0.0659(4) Uani 1 1 d . . . C4 C 0.9216(3) 1.09926(10) 0.71222(6) 0.0573(3) Uani 1 1 d . . . C21 C 0.7090(3) 1.43926(11) 0.55375(6) 0.0651(4) Uani 1 1 d . . . H21 H 0.5733 1.4429 0.5793 0.078 Uiso 1 1 calc R . . C6 C 0.5858(3) 1.20223(9) 0.74248(6) 0.0594(3) Uani 1 1 d . . . C20 C 0.7439(3) 1.51350(11) 0.50980(6) 0.0619(3) Uani 1 1 d . . . C3 C 1.1105(3) 1.06034(11) 0.67843(7) 0.0687(4) Uani 1 1 d . . . H3 H 1.1611 1.0824 0.6400 0.082 Uiso 1 1 calc R . . C12 C 0.8652(3) 1.36263(10) 0.56041(6) 0.0641(4) Uani 1 1 d . . . C10 C 0.7987(3) 1.23817(10) 0.64938(7) 0.0682(4) Uani 1 1 d . . . C1 C 1.0792(3) 0.97775(11) 0.76437(7) 0.0677(4) Uani 1 1 d . . . H1 H 1.1092 0.9315 0.7956 0.081 Uiso 1 1 calc R . . C7 C 0.4031(3) 1.27326(11) 0.74037(8) 0.0728(4) Uani 1 1 d . . . H7 H 0.3796 1.3216 0.7099 0.087 Uiso 1 1 calc R . . C2 C 1.2094(3) 0.98426(12) 0.71120(7) 0.0748(4) Uani 1 1 d . . . H2 H 1.3409 0.9440 0.6998 0.090 Uiso 1 1 calc R . . C11 C 0.8306(3) 1.29309(11) 0.60799(7) 0.0690(4) Uani 1 1 d . . . C16 C 0.9810(3) 1.58272(14) 0.42852(7) 0.0821(5) Uani 1 1 d . . . H16 H 1.1159 1.5801 0.4027 0.099 Uiso 1 1 calc R . . C8 C 0.2647(3) 1.25973(12) 0.79067(8) 0.0777(4) Uani 1 1 d . . . H8 H 0.1271 1.2969 0.8014 0.093 Uiso 1 1 calc R . . C13 C 1.0659(3) 1.35545(12) 0.52162(7) 0.0762(4) Uani 1 1 d . . . H13 H 1.1748 1.3019 0.5257 0.091 Uiso 1 1 calc R . . C9 C 0.3628(3) 1.18163(12) 0.82308(7) 0.0707(4) Uani 1 1 d . . . H9 H 0.3017 1.1565 0.8599 0.085 Uiso 1 1 calc R . . C19 C 0.5857(4) 1.59450(13) 0.50348(7) 0.0769(4) Uani 1 1 d . . . H19 H 0.4496 1.5993 0.5288 0.092 Uiso 1 1 calc R . . C14 C 1.1016(3) 1.42560(13) 0.47857(7) 0.0786(4) Uani 1 1 d . . . H14 H 1.2353 1.4198 0.4525 0.094 Uiso 1 1 calc R . . C18 C 0.6270(4) 1.66564(14) 0.46145(8) 0.0876(5) Uani 1 1 d . . . H18 H 0.5204 1.7200 0.4578 0.105 Uiso 1 1 calc R . . B1 B 0.7306(3) 1.06662(12) 0.81713(8) 0.0618(4) Uani 1 1 d . . . C17 C 0.8244(4) 1.65908(14) 0.42387(8) 0.0891(5) Uani 1 1 d . . . H17 H 0.8503 1.7088 0.3944 0.107 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 F1 0.0942(7) 0.0629(5) 0.1033(7) 0.0191(5) 0.0298(6) -0.0045(5) F2 0.0822(6) 0.1086(7) 0.0630(5) -0.0095(5) -0.0091(5) 0.0120(5) N1 0.0594(7) 0.0513(6) 0.0605(6) 0.0012(5) -0.0007(5) -0.0037(5) N2 0.0544(6) 0.0557(6) 0.0677(7) -0.0046(5) -0.0017(5) -0.0063(5) C5 0.0662(8) 0.0476(6) 0.0631(7) -0.0001(6) -0.0076(6) -0.0090(6) C15 0.0742(9) 0.0705(8) 0.0532(7) -0.0017(6) 0.0011(7) -0.0107(8) C4 0.0609(8) 0.0521(6) 0.0588(7) -0.0022(6) -0.0027(6) -0.0075(6) C21 0.0728(9) 0.0666(8) 0.0560(7) 0.0036(6) 0.0070(7) -0.0035(7) C6 0.0598(8) 0.0475(6) 0.0708(8) -0.0010(6) -0.0082(7) -0.0062(6) C20 0.0696(9) 0.0626(8) 0.0534(7) 0.0003(6) -0.0004(6) -0.0067(7) C3 0.0734(9) 0.0705(9) 0.0623(8) -0.0043(7) 0.0062(7) -0.0054(8) C12 0.0795(10) 0.0577(7) 0.0552(7) -0.0004(6) 0.0000(7) -0.0070(7) C10 0.0829(10) 0.0560(7) 0.0657(8) 0.0024(7) -0.0077(8) -0.0070(7) C1 0.0684(9) 0.0609(8) 0.0737(9) 0.0039(7) -0.0048(8) 0.0064(7) C7 0.0702(9) 0.0561(8) 0.0921(11) -0.0024(8) -0.0147(9) -0.0002(7) C2 0.0733(10) 0.0729(10) 0.0781(10) -0.0063(8) 0.0041(8) 0.0087(8) C11 0.0846(11) 0.0570(8) 0.0654(8) -0.0016(7) -0.0062(8) -0.0057(7) C16 0.0888(12) 0.0941(12) 0.0635(9) 0.0107(9) 0.0052(8) -0.0242(10) C8 0.0612(9) 0.0714(9) 0.1005(12) -0.0122(9) -0.0077(9) 0.0053(8) C13 0.0801(11) 0.0696(9) 0.0787(10) -0.0038(8) 0.0068(9) 0.0071(9) C9 0.0581(9) 0.0731(9) 0.0808(9) -0.0110(8) 0.0014(7) -0.0070(8) C19 0.0833(11) 0.0738(9) 0.0736(9) 0.0070(8) 0.0013(8) 0.0047(9) C14 0.0783(11) 0.0857(10) 0.0717(9) -0.0045(8) 0.0194(9) -0.0045(9) C18 0.1036(14) 0.0741(10) 0.0851(11) 0.0136(9) -0.0118(11) 0.0023(11) B1 0.0645(10) 0.0573(8) 0.0636(9) 0.0030(7) 0.0031(8) -0.0033(8) C17 0.1107(15) 0.0801(11) 0.0763(10) 0.0211(9) -0.0070(10) -0.0179(11) _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 F1 B1 1.3757(19) . ? F2 B1 1.389(2) . ? N1 C1 1.3429(19) . ? N1 C4 1.3832(16) . ? N1 B1 1.540(2) . ? N2 C9 1.3468(19) . ? N2 C6 1.3849(17) . ? N2 B1 1.542(2) . ? C5 C4 1.401(2) . ? C5 C6 1.402(2) . ? C5 C10 1.4203(19) . ? C15 C20 1.413(2) . ? C15 C14 1.415(2) . ? C15 C16 1.419(2) . ? C4 C3 1.400(2) . ? C21 C12 1.364(2) . ? C21 C20 1.4150(19) . ? C21 H21 0.9500 . ? C6 C7 1.403(2) . ? C20 C19 1.415(2) . ? C3 C2 1.377(2) . ? C3 H3 0.9500 . ? C12 C13 1.421(2) . ? C12 C11 1.429(2) . ? C10 C11 1.197(2) . ? C1 C2 1.393(2) . ? C1 H1 0.9500 . ? C7 C8 1.374(2) . ? C7 H7 0.9500 . ? C2 H2 0.9500 . ? C16 C17 1.358(3) . ? C16 H16 0.9500 . ? C8 C9 1.391(2) . ? C8 H8 0.9500 . ? C13 C14 1.363(2) . ? C13 H13 0.9500 . ? C9 H9 0.9500 . ? C19 C18 1.361(2) . ? C19 H19 0.9500 . ? C14 H14 0.9500 . ? C18 C17 1.389(3) . ? C18 H18 0.9500 . ? C17 H17 0.9500 . ? 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 C1 N1 C4 107.30(12) . . ? C1 N1 B1 126.44(12) . . ? C4 N1 B1 126.13(12) . . ? C9 N2 C6 107.59(13) . . ? C9 N2 B1 126.70(13) . . ? C6 N2 B1 125.54(12) . . ? C4 C5 C6 120.58(12) . . ? C4 C5 C10 119.73(14) . . ? C6 C5 C10 119.67(14) . . ? C20 C15 C14 118.55(14) . . ? C20 C15 C16 118.38(15) . . ? C14 C15 C16 123.07(16) . . ? N1 C4 C3 108.28(13) . . ? N1 C4 C5 120.18(13) . . ? C3 C4 C5 131.51(13) . . ? C12 C21 C20 121.65(14) . . ? C12 C21 H21 119.2 . . ? C20 C21 H21 119.2 . . ? N2 C6 C5 120.39(12) . . ? N2 C6 C7 108.20(13) . . ? C5 C6 C7 131.33(14) . . ? C15 C20 C19 119.18(14) . . ? C15 C20 C21 118.77(14) . . ? C19 C20 C21 122.04(15) . . ? C2 C3 C4 107.41(14) . . ? C2 C3 H3 126.3 . . ? C4 C3 H3 126.3 . . ? C21 C12 C13 119.55(14) . . ? C21 C12 C11 119.51(14) . . ? C13 C12 C11 120.88(15) . . ? C11 C10 C5 175.51(16) . . ? N1 C1 C2 110.33(14) . . ? N1 C1 H1 124.8 . . ? C2 C1 H1 124.8 . . ? C8 C7 C6 107.04(14) . . ? C8 C7 H7 126.5 . . ? C6 C7 H7 126.5 . . ? C3 C2 C1 106.68(15) . . ? C3 C2 H2 126.7 . . ? C1 C2 H2 126.7 . . ? C10 C11 C12 177.18(16) . . ? C17 C16 C15 120.53(17) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C7 C8 C9 107.51(15) . . ? C7 C8 H8 126.2 . . ? C9 C8 H8 126.2 . . ? C14 C13 C12 119.77(16) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? N2 C9 C8 109.66(15) . . ? N2 C9 H9 125.2 . . ? C8 C9 H9 125.2 . . ? C18 C19 C20 120.54(18) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C13 C14 C15 121.70(16) . . ? C13 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? C19 C18 C17 120.28(18) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? F1 B1 F2 109.48(13) . . ? F1 B1 N1 110.19(12) . . ? F2 B1 N1 110.53(13) . . ? F1 B1 N2 110.68(14) . . ? F2 B1 N2 109.71(12) . . ? N1 B1 N2 106.21(12) . . ? C16 C17 C18 121.08(16) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? 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 C1 N1 C4 C3 0.72(15) . . . . ? B1 N1 C4 C3 176.80(13) . . . . ? C1 N1 C4 C5 -177.40(12) . . . . ? B1 N1 C4 C5 -1.3(2) . . . . ? C6 C5 C4 N1 -3.79(19) . . . . ? C10 C5 C4 N1 174.77(12) . . . . ? C6 C5 C4 C3 178.60(14) . . . . ? C10 C5 C4 C3 -2.8(2) . . . . ? C9 N2 C6 C5 -176.29(12) . . . . ? B1 N2 C6 C5 8.2(2) . . . . ? C9 N2 C6 C7 0.74(15) . . . . ? B1 N2 C6 C7 -174.74(13) . . . . ? C4 C5 C6 N2 0.46(19) . . . . ? C10 C5 C6 N2 -178.09(13) . . . . ? C4 C5 C6 C7 -175.77(14) . . . . ? C10 C5 C6 C7 5.7(2) . . . . ? C14 C15 C20 C19 179.86(15) . . . . ? C16 C15 C20 C19 0.5(2) . . . . ? C14 C15 C20 C21 0.6(2) . . . . ? C16 C15 C20 C21 -178.73(14) . . . . ? C12 C21 C20 C15 0.7(2) . . . . ? C12 C21 C20 C19 -178.51(15) . . . . ? N1 C4 C3 C2 -0.53(17) . . . . ? C5 C4 C3 C2 177.30(15) . . . . ? C20 C21 C12 C13 -1.3(2) . . . . ? C20 C21 C12 C11 175.94(14) . . . . ? C4 C5 C10 C11 -108(2) . . . . ? C6 C5 C10 C11 70(3) . . . . ? C4 N1 C1 C2 -0.65(17) . . . . ? B1 N1 C1 C2 -176.71(13) . . . . ? N2 C6 C7 C8 -0.60(16) . . . . ? C5 C6 C7 C8 175.98(14) . . . . ? C4 C3 C2 C1 0.14(18) . . . . ? N1 C1 C2 C3 0.32(19) . . . . ? C5 C10 C11 C12 -35(6) . . . . ? C21 C12 C11 C10 -39(4) . . . . ? C13 C12 C11 C10 138(4) . . . . ? C20 C15 C16 C17 -0.7(2) . . . . ? C14 C15 C16 C17 -179.99(17) . . . . ? C6 C7 C8 C9 0.24(18) . . . . ? C21 C12 C13 C14 0.6(2) . . . . ? C11 C12 C13 C14 -176.59(15) . . . . ? C6 N2 C9 C8 -0.59(16) . . . . ? B1 N2 C9 C8 174.82(13) . . . . ? C7 C8 C9 N2 0.22(18) . . . . ? C15 C20 C19 C18 -0.4(2) . . . . ? C21 C20 C19 C18 178.75(17) . . . . ? C12 C13 C14 C15 0.7(3) . . . . ? C20 C15 C14 C13 -1.3(2) . . . . ? C16 C15 C14 C13 178.00(17) . . . . ? C20 C19 C18 C17 0.5(3) . . . . ? C1 N1 B1 F1 -56.7(2) . . . . ? C4 N1 B1 F1 127.95(14) . . . . ? C1 N1 B1 F2 64.43(18) . . . . ? C4 N1 B1 F2 -110.91(15) . . . . ? C1 N1 B1 N2 -176.63(12) . . . . ? C4 N1 B1 N2 8.03(18) . . . . ? C9 N2 B1 F1 54.31(19) . . . . ? C6 N2 B1 F1 -131.07(13) . . . . ? C9 N2 B1 F2 -66.62(18) . . . . ? C6 N2 B1 F2 108.00(15) . . . . ? C9 N2 B1 N1 173.91(12) . . . . ? C6 N2 B1 N1 -11.47(18) . . . . ? C15 C16 C17 C18 0.8(3) . . . . ? C19 C18 C17 C16 -0.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 72.10 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.081 _refine_diff_density_min -0.099 _refine_diff_density_rms 0.022 _database_code_depnum_ccdc_archive 'CCDC 967406' ####################################################################### # # 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_rm107 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H13 B F2 N2' _chemical_formula_weight 342.14 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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 10.1059(3) _cell_length_b 10.4411(3) _cell_length_c 15.6091(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.699(3) _cell_angle_gamma 90.00 _cell_volume 1618.39(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4939 _cell_measurement_theta_min 4.2308 _cell_measurement_theta_max 72.0138 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.811 _exptl_absorpt_correction_T_min 0.7757 _exptl_absorpt_correction_T_max 0.8612 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Micro-Focus (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'OXFORD DIFFRACTION SUPER NOVA' _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean 15.9948 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10226 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0204 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.23 _diffrn_reflns_theta_max 72.16 _reflns_number_total 3147 _reflns_number_gt 2590 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd.,' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd.,' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Ortep3 _computing_publication_material Shelx97 _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^)+(0.0791P)^2^+0.1597P] 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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0032(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3147 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0519 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1387 _refine_ls_wR_factor_gt 0.1244 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.000 _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 F1 F 0.44269(10) 0.95638(11) 0.09500(7) 0.0736(3) Uani 1 1 d . . . F2 F 0.29437(12) 1.09398(9) 0.13634(7) 0.0789(4) Uani 1 1 d . . . B1 B 0.30915(19) 0.97428(17) 0.10199(13) 0.0524(4) Uani 1 1 d . . . N1 N 0.21631(13) 0.96188(11) 0.01130(8) 0.0481(3) Uani 1 1 d . . . N2 N 0.26413(12) 0.86843(12) 0.15953(8) 0.0498(3) Uani 1 1 d . . . C1 C 0.21959(18) 1.03426(15) -0.05869(11) 0.0578(4) Uani 1 1 d . . . H1 H 0.2833 1.1003 -0.0614 0.069 Uiso 1 1 calc R . . C2 C 0.11667(18) 0.99973(17) -0.12728(11) 0.0600(4) Uani 1 1 d . . . H2 H 0.0981 1.0373 -0.1837 0.072 Uiso 1 1 calc R . . C3 C 0.04745(16) 0.90145(15) -0.09790(10) 0.0529(4) Uani 1 1 d . . . H3 H -0.0283 0.8580 -0.1301 0.063 Uiso 1 1 calc R . . C4 C 0.10962(15) 0.87682(13) -0.01093(10) 0.0464(4) Uani 1 1 d . . . C5 C 0.08238(15) 0.78627(13) 0.04890(10) 0.0457(4) Uani 1 1 d . . . C6 C 0.16127(16) 0.78075(13) 0.13327(10) 0.0480(4) Uani 1 1 d . . . C7 C 0.15605(17) 0.69831(16) 0.20276(11) 0.0553(4) Uani 1 1 d . . . H7 H 0.0954 0.6288 0.2029 0.066 Uiso 1 1 calc R . . C8 C 0.25483(18) 0.73585(18) 0.27120(11) 0.0621(4) Uani 1 1 d . . . H8 H 0.2751 0.6973 0.3272 0.075 Uiso 1 1 calc R . . C9 C 0.31914(17) 0.84070(17) 0.24278(11) 0.0590(4) Uani 1 1 d . . . H9 H 0.3915 0.8863 0.2771 0.071 Uiso 1 1 calc R . . C10 C -0.02613(16) 0.69893(13) 0.02626(10) 0.0495(4) Uani 1 1 d . . . C11 C -0.11826(15) 0.62485(14) 0.00958(10) 0.0491(4) Uani 1 1 d . . . C12 C -0.22768(15) 0.53624(14) -0.01018(10) 0.0482(4) Uani 1 1 d . . . C13 C -0.31218(17) 0.54117(16) -0.09031(11) 0.0578(4) Uani 1 1 d . . . H13 H -0.2991 0.6049 -0.1314 0.069 Uiso 1 1 calc R . . C14 C -0.41771(19) 0.45216(19) -0.11141(12) 0.0670(5) Uani 1 1 d . . . H14 H -0.4745 0.4552 -0.1672 0.080 Uiso 1 1 calc R . . C15 C -0.43921(17) 0.36206(17) -0.05289(13) 0.0638(5) Uani 1 1 d . . . H15 H -0.5104 0.3022 -0.0685 0.077 Uiso 1 1 calc R . . C16 C -0.35746(16) 0.35588(14) 0.03076(11) 0.0539(4) Uani 1 1 d . . . C17 C -0.3813(2) 0.26637(16) 0.09410(15) 0.0689(5) Uani 1 1 d . . . H17 H -0.4531 0.2068 0.0798 0.083 Uiso 1 1 calc R . . C18 C -0.3037(2) 0.26381(18) 0.17510(15) 0.0763(6) Uani 1 1 d . . . H18 H -0.3229 0.2044 0.2173 0.092 Uiso 1 1 calc R . . C19 C -0.1959(2) 0.34845(18) 0.19617(13) 0.0716(5) Uani 1 1 d . . . H19 H -0.1409 0.3453 0.2525 0.086 Uiso 1 1 calc R . . C20 C -0.16850(18) 0.43534(16) 0.13716(11) 0.0561(4) Uani 1 1 d . . . H20 H -0.0940 0.4916 0.1526 0.067 Uiso 1 1 calc R . . C21 C -0.24911(15) 0.44342(13) 0.05300(10) 0.0473(4) Uani 1 1 d . . . 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 F1 0.0434(6) 0.0983(8) 0.0781(7) 0.0164(6) 0.0084(5) -0.0148(5) F2 0.0994(9) 0.0566(6) 0.0751(7) -0.0149(5) 0.0015(6) -0.0144(6) B1 0.0464(10) 0.0522(9) 0.0569(10) -0.0038(7) 0.0054(8) -0.0106(7) N1 0.0454(7) 0.0447(6) 0.0548(7) -0.0028(5) 0.0113(6) -0.0066(5) N2 0.0431(7) 0.0567(7) 0.0496(7) -0.0055(5) 0.0087(5) -0.0062(5) C1 0.0588(10) 0.0540(9) 0.0622(10) 0.0046(7) 0.0151(8) -0.0090(7) C2 0.0630(11) 0.0621(9) 0.0543(9) 0.0047(7) 0.0095(8) -0.0034(8) C3 0.0501(9) 0.0533(8) 0.0541(9) -0.0054(7) 0.0064(7) -0.0005(7) C4 0.0432(8) 0.0426(7) 0.0542(8) -0.0051(6) 0.0114(6) -0.0013(6) C5 0.0413(8) 0.0415(7) 0.0552(8) -0.0054(6) 0.0113(6) -0.0011(6) C6 0.0448(8) 0.0465(7) 0.0544(9) -0.0032(6) 0.0138(7) -0.0042(6) C7 0.0528(9) 0.0582(9) 0.0564(9) 0.0026(7) 0.0136(7) -0.0052(7) C8 0.0594(11) 0.0769(11) 0.0502(9) 0.0053(8) 0.0103(8) -0.0037(8) C9 0.0511(9) 0.0756(11) 0.0500(9) -0.0062(8) 0.0088(7) -0.0067(8) C10 0.0476(9) 0.0460(7) 0.0559(9) -0.0009(6) 0.0117(7) -0.0022(6) C11 0.0474(8) 0.0462(7) 0.0554(9) -0.0027(6) 0.0134(7) -0.0017(6) C12 0.0446(8) 0.0483(7) 0.0533(8) -0.0082(6) 0.0130(7) -0.0020(6) C13 0.0539(10) 0.0666(10) 0.0536(9) -0.0005(7) 0.0116(8) -0.0018(7) C14 0.0521(10) 0.0851(12) 0.0595(10) -0.0149(9) -0.0007(8) -0.0060(9) C15 0.0506(10) 0.0625(10) 0.0784(12) -0.0146(8) 0.0119(9) -0.0107(7) C16 0.0463(9) 0.0476(8) 0.0705(10) -0.0125(7) 0.0177(8) -0.0035(6) C17 0.0645(12) 0.0521(9) 0.0953(15) -0.0026(9) 0.0285(11) -0.0098(8) C18 0.0901(15) 0.0634(10) 0.0825(14) 0.0135(10) 0.0341(12) 0.0012(10) C19 0.0863(14) 0.0677(11) 0.0617(11) 0.0040(8) 0.0160(10) 0.0035(10) C20 0.0596(10) 0.0529(8) 0.0551(9) -0.0061(7) 0.0086(8) -0.0022(7) C21 0.0463(8) 0.0431(7) 0.0546(9) -0.0092(6) 0.0152(7) -0.0001(6) _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 F1 B1 1.387(2) . ? F2 B1 1.379(2) . ? B1 N2 1.545(2) . ? B1 N1 1.552(2) . ? N1 C1 1.334(2) . ? N1 C4 1.3903(18) . ? N2 C9 1.346(2) . ? N2 C6 1.3887(18) . ? C1 C2 1.394(2) . ? C1 H1 0.9500 . ? C2 C3 1.368(2) . ? C2 H2 0.9500 . ? C3 C4 1.410(2) . ? C3 H3 0.9500 . ? C4 C5 1.392(2) . ? C5 C6 1.408(2) . ? C5 C10 1.420(2) . ? C6 C7 1.393(2) . ? C7 C8 1.377(2) . ? C7 H7 0.9500 . ? C8 C9 1.387(2) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.201(2) . ? C11 C12 1.431(2) . ? C12 C13 1.378(2) . ? C12 C21 1.428(2) . ? C13 C14 1.407(2) . ? C13 H13 0.9500 . ? C14 C15 1.357(3) . ? C14 H14 0.9500 . ? C15 C16 1.411(2) . ? C15 H15 0.9500 . ? C16 C17 1.413(2) . ? C16 C21 1.419(2) . ? C17 C18 1.359(3) . ? C17 H17 0.9500 . ? C18 C19 1.394(3) . ? C18 H18 0.9500 . ? C19 C20 1.358(2) . ? C19 H19 0.9500 . ? C20 C21 1.414(2) . ? C20 H20 0.9500 . ? 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 F2 B1 F1 109.27(14) . . ? F2 B1 N2 110.95(14) . . ? F1 B1 N2 110.20(14) . . ? F2 B1 N1 109.85(14) . . ? F1 B1 N1 110.45(14) . . ? N2 B1 N1 106.09(12) . . ? C1 N1 C4 107.07(13) . . ? C1 N1 B1 126.67(13) . . ? C4 N1 B1 126.20(12) . . ? C9 N2 C6 107.18(13) . . ? C9 N2 B1 126.97(13) . . ? C6 N2 B1 125.81(13) . . ? N1 C1 C2 110.73(14) . . ? N1 C1 H1 124.6 . . ? C2 C1 H1 124.6 . . ? C3 C2 C1 106.95(15) . . ? C3 C2 H2 126.5 . . ? C1 C2 H2 126.5 . . ? C2 C3 C4 107.18(15) . . ? C2 C3 H3 126.4 . . ? C4 C3 H3 126.4 . . ? N1 C4 C5 120.48(14) . . ? N1 C4 C3 108.07(13) . . ? C5 C4 C3 131.44(14) . . ? C4 C5 C6 120.47(13) . . ? C4 C5 C10 120.61(14) . . ? C6 C5 C10 118.91(13) . . ? N2 C6 C7 108.18(14) . . ? N2 C6 C5 120.78(13) . . ? C7 C6 C5 131.04(14) . . ? C8 C7 C6 107.54(15) . . ? C8 C7 H7 126.2 . . ? C6 C7 H7 126.2 . . ? C7 C8 C9 106.96(15) . . ? C7 C8 H8 126.5 . . ? C9 C8 H8 126.5 . . ? N2 C9 C8 110.14(15) . . ? N2 C9 H9 124.9 . . ? C8 C9 H9 124.9 . . ? C11 C10 C5 178.13(16) . . ? C10 C11 C12 179.8(2) . . ? C13 C12 C21 120.29(14) . . ? C13 C12 C11 119.68(14) . . ? C21 C12 C11 120.02(14) . . ? C12 C13 C14 120.19(16) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 120.64(17) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 121.02(15) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C15 C16 C17 122.06(16) . . ? C15 C16 C21 119.31(15) . . ? C17 C16 C21 118.62(16) . . ? C18 C17 C16 121.32(17) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C17 C18 C19 119.87(18) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C20 C19 C18 120.83(19) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C21 121.02(16) . . ? C19 C20 H20 119.5 . . ? C21 C20 H20 119.5 . . ? C20 C21 C16 118.31(14) . . ? C20 C21 C12 123.17(14) . . ? C16 C21 C12 118.51(15) . . ? 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 F2 B1 N1 C1 60.0(2) . . . . ? F1 B1 N1 C1 -60.6(2) . . . . ? N2 B1 N1 C1 -179.98(14) . . . . ? F2 B1 N1 C4 -116.66(15) . . . . ? F1 B1 N1 C4 122.74(15) . . . . ? N2 B1 N1 C4 3.3(2) . . . . ? F2 B1 N2 C9 -62.9(2) . . . . ? F1 B1 N2 C9 58.3(2) . . . . ? N1 B1 N2 C9 177.86(14) . . . . ? F2 B1 N2 C6 119.58(16) . . . . ? F1 B1 N2 C6 -119.26(16) . . . . ? N1 B1 N2 C6 0.3(2) . . . . ? C4 N1 C1 C2 0.30(18) . . . . ? B1 N1 C1 C2 -176.91(15) . . . . ? N1 C1 C2 C3 -0.1(2) . . . . ? C1 C2 C3 C4 -0.07(18) . . . . ? C1 N1 C4 C5 178.63(13) . . . . ? B1 N1 C4 C5 -4.1(2) . . . . ? C1 N1 C4 C3 -0.34(16) . . . . ? B1 N1 C4 C3 176.88(13) . . . . ? C2 C3 C4 N1 0.25(17) . . . . ? C2 C3 C4 C5 -178.56(15) . . . . ? N1 C4 C5 C6 1.0(2) . . . . ? C3 C4 C5 C6 179.64(14) . . . . ? N1 C4 C5 C10 -179.73(12) . . . . ? C3 C4 C5 C10 -1.0(2) . . . . ? C9 N2 C6 C7 -0.46(16) . . . . ? B1 N2 C6 C7 177.49(14) . . . . ? C9 N2 C6 C5 178.93(14) . . . . ? B1 N2 C6 C5 -3.1(2) . . . . ? C4 C5 C6 N2 2.5(2) . . . . ? C10 C5 C6 N2 -176.80(13) . . . . ? C4 C5 C6 C7 -178.24(15) . . . . ? C10 C5 C6 C7 2.4(2) . . . . ? N2 C6 C7 C8 0.27(18) . . . . ? C5 C6 C7 C8 -179.04(16) . . . . ? C6 C7 C8 C9 0.02(19) . . . . ? C6 N2 C9 C8 0.48(18) . . . . ? B1 N2 C9 C8 -177.44(15) . . . . ? C7 C8 C9 N2 -0.3(2) . . . . ? C4 C5 C10 C11 -152(5) . . . . ? C6 C5 C10 C11 27(5) . . . . ? C5 C10 C11 C12 -76(51) . . . . ? C10 C11 C12 C13 -134(100) . . . . ? C10 C11 C12 C21 46(49) . . . . ? C21 C12 C13 C14 -2.0(2) . . . . ? C11 C12 C13 C14 178.14(15) . . . . ? C12 C13 C14 C15 1.2(3) . . . . ? C13 C14 C15 C16 0.6(3) . . . . ? C14 C15 C16 C17 177.31(16) . . . . ? C14 C15 C16 C21 -1.6(2) . . . . ? C15 C16 C17 C18 -178.33(17) . . . . ? C21 C16 C17 C18 0.6(2) . . . . ? C16 C17 C18 C19 -1.7(3) . . . . ? C17 C18 C19 C20 1.1(3) . . . . ? C18 C19 C20 C21 0.6(3) . . . . ? C19 C20 C21 C16 -1.7(2) . . . . ? C19 C20 C21 C12 177.51(15) . . . . ? C15 C16 C21 C20 -179.95(14) . . . . ? C17 C16 C21 C20 1.1(2) . . . . ? C15 C16 C21 C12 0.8(2) . . . . ? C17 C16 C21 C12 -178.14(13) . . . . ? C13 C12 C21 C20 -178.26(14) . . . . ? C11 C12 C21 C20 1.6(2) . . . . ? C13 C12 C21 C16 1.0(2) . . . . ? C11 C12 C21 C16 -179.14(12) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 72.16 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.198 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.041 #===END _database_code_depnum_ccdc_archive 'CCDC 967407'