# Electronic Supplementary Material (ESI) for RSC Advances # 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_1 #TrackingRef 'CIFcarine090112.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 15.4580(3) _cell_length_b 9.54826(16) _cell_length_c 20.4320(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3015.70(9) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_space_group_name_Hall '-P 2ac 2ab ' 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+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 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 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 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' P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C16 H17 N4 O1 P1 # Dc = 1.38 Fooo = 1312.00 Mu = 16.78 M = 312.31 # Found Formula = C16 H17 N4 O1 P1 # Dc = 1.38 FOOO = 1312.00 Mu = 16.78 M = 312.31 _chemical_formula_sum 'C16 H17 N4 O1 P1' _chemical_formula_moiety 'C16 H17 N4 O1 P1' _chemical_compound_source ? _chemical_formula_weight 312.31 _cell_measurement_reflns_used 9972 _cell_measurement_theta_min 4 _cell_measurement_theta_max 62 _cell_measurement_temperature 100 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.200 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_max 0.300 _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 1.678 # Sheldrick geometric approximatio 0.60 0.71 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis, (Oxford Diffraction, 2002)' _exptl_absorpt_correction_T_min 0.59 _exptl_absorpt_correction_T_max 0.71 _diffrn_measurement_device_type 'Oxford Diffraction Gemini' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Gemini, (Oxford Diffraction, 2006)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _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 100 _diffrn_reflns_number 12506 _reflns_number_total 2365 _diffrn_reflns_av_R_equivalents 0.016 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 2365 # Theoretical number of reflections is about 4743 _diffrn_reflns_theta_min 4.328 _diffrn_reflns_theta_max 61.987 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 61.987 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min 0 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _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 difmap _refine_diff_density_min -0.35 _refine_diff_density_max 0.36 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 2311 _refine_ls_number_restraints 0 _refine_ls_number_parameters 200 _oxford_refine_ls_R_factor_ref 0.0303 _refine_ls_wR_factor_ref 0.0425 _refine_ls_goodness_of_fit_ref 0.9638 _refine_ls_shift/su_max 0.0013963 _refine_ls_shift/su_mean 0.0001117 # The values computed from all data _oxford_reflns_number_all 2357 _refine_ls_R_factor_all 0.0310 _refine_ls_wR_factor_all 0.0428 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2340 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_gt 0.0427 # 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: 14.3 11.5 13.0 4.59 ; # 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 C1 C 0.52059(7) 0.96086(10) 0.65373(5) 0.0150 1.0000 Uani . . . . . . C2 C 0.37793(5) 0.75819(10) 0.66781(5) 0.0116 1.0000 Uani . . . . . . C3 C 0.28044(6) 0.74271(11) 0.74201(5) 0.0148 1.0000 Uani . . . . . . C4 C 0.27375(6) 0.62336(10) 0.70620(4) 0.0127 1.0000 Uani . . . . . . C5 C 0.34654(7) 0.53109(10) 0.60721(5) 0.0129 1.0000 Uani . . . . . . C6 C 0.27068(6) 0.47753(11) 0.58010(5) 0.0161 1.0000 Uani . . . . . . C7 C 0.27263(7) 0.37000(12) 0.53497(5) 0.0194 1.0000 Uani . . . . . . C8 C 0.35203(7) 0.31752(10) 0.51473(5) 0.0194 1.0000 Uani . . . . . . C9 C 0.42793(6) 0.37367(10) 0.53864(4) 0.0162 1.0000 Uani . . . . . . C10 C 0.42649(6) 0.48008(10) 0.58548(4) 0.0126 1.0000 Uani . . . . . . C11 C 0.57871(7) 0.43987(10) 0.62020(5) 0.0168 1.0000 Uani . . . . . . C12 C 0.64375(7) 0.52263(11) 0.64176(5) 0.0178 1.0000 Uani . . . . . . C13 C 0.53533(6) 0.65921(12) 0.62712(5) 0.0122 1.0000 Uani . . . . . . C14 C 0.45743(7) 1.08408(11) 0.65006(6) 0.0225 1.0000 Uani . . . . . . C15 C 0.54614(7) 0.93338(12) 0.72509(5) 0.0202 1.0000 Uani . . . . . . C16 C 0.60089(7) 0.99471(11) 0.61174(5) 0.0188 1.0000 Uani . . . . . . N1 N 0.34549(5) 0.82711(8) 0.71801(4) 0.0144 1.0000 Uani . . . . . . N2 N 0.33675(5) 0.63210(8) 0.65836(4) 0.0112 1.0000 Uani . . . . . . N3 N 0.50776(6) 0.52603(9) 0.61099(4) 0.0120 1.0000 Uani . . . . . . N4 N 0.61714(5) 0.65993(9) 0.64612(4) 0.0153 1.0000 Uani . . . . . . O1 O 0.44105(4) 0.82983(7) 0.54659(3) 0.0152 1.0000 Uani . . . . . . P1 P 0.466998(15) 0.81041(2) 0.615973(11) 0.0101 1.0000 Uani . . . . . . H31 H 0.2458 0.7665 0.7801 0.0181 1.0000 Uiso R . . . . . H41 H 0.2350 0.5463 0.7119 0.0150 1.0000 Uiso R . . . . . H61 H 0.2159 0.5174 0.5928 0.0188 1.0000 Uiso R . . . . . H71 H 0.2183 0.3323 0.5174 0.0239 1.0000 Uiso R . . . . . H81 H 0.3545 0.2433 0.4822 0.0236 1.0000 Uiso R . . . . . H91 H 0.4825 0.3394 0.5236 0.0198 1.0000 Uiso R . . . . . H111 H 0.5782 0.3401 0.6127 0.0214 1.0000 Uiso R . . . . . H121 H 0.7005 0.4899 0.6552 0.0228 1.0000 Uiso R . . . . . H141 H 0.4387 1.1034 0.6027 0.0360 1.0000 Uiso R . . . . . H142 H 0.4869 1.1685 0.6675 0.0349 1.0000 Uiso R . . . . . H143 H 0.4070 1.0645 0.6778 0.0351 1.0000 Uiso R . . . . . H151 H 0.5879 0.8556 0.7258 0.0328 1.0000 Uiso R . . . . . H152 H 0.5739 1.0208 0.7405 0.0321 1.0000 Uiso R . . . . . H153 H 0.4951 0.9145 0.7518 0.0330 1.0000 Uiso R . . . . . H161 H 0.6415 0.9156 0.6142 0.0298 1.0000 Uiso R . . . . . H162 H 0.6271 1.0785 0.6307 0.0296 1.0000 Uiso R . . . . . H163 H 0.5836 1.0152 0.5656 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 0.0119(5) 0.0141(5) 0.0189(5) -0.0030(4) 0.0010(4) -0.0045(4) C2 0.0077(5) 0.0117(5) 0.0153(5) 0.0010(4) -0.0015(4) 0.0009(4) C3 0.0110(5) 0.0179(6) 0.0156(5) -0.0001(4) 0.0036(4) 0.0012(4) C4 0.0081(5) 0.0136(5) 0.0165(5) 0.0022(4) 0.0009(3) 0.0001(3) C5 0.0146(6) 0.0119(5) 0.0120(5) 0.0006(4) 0.0010(3) -0.0011(4) C6 0.0131(5) 0.0188(5) 0.0166(5) 0.0013(4) 0.0015(4) -0.0023(4) C7 0.0207(6) 0.0217(6) 0.0159(5) -0.0017(4) 0.0008(4) -0.0091(4) C8 0.0273(6) 0.0173(5) 0.0138(5) -0.0033(4) 0.0043(4) -0.0064(4) C9 0.0198(6) 0.0145(5) 0.0143(5) 0.0014(4) 0.0065(4) -0.0007(4) C10 0.0131(5) 0.0116(5) 0.0131(5) 0.0029(3) 0.0009(4) -0.0025(4) C11 0.0139(6) 0.0140(5) 0.0225(5) 0.0032(4) 0.0057(4) 0.0050(4) C12 0.0103(5) 0.0213(6) 0.0217(5) 0.0052(4) 0.0025(4) 0.0047(4) C13 0.0113(6) 0.0146(5) 0.0108(4) 0.0014(4) 0.0018(3) -0.0006(4) C14 0.0170(5) 0.0136(5) 0.0369(7) -0.0032(4) 0.0041(4) -0.0030(4) C15 0.0162(5) 0.0264(6) 0.0179(6) -0.0061(5) -0.0004(4) -0.0051(4) C16 0.0150(6) 0.0171(5) 0.0242(6) -0.0016(4) 0.0029(4) -0.0062(5) N1 0.0108(4) 0.0149(4) 0.0176(4) -0.0014(3) 0.0016(3) 0.0008(3) N2 0.0075(4) 0.0117(4) 0.0143(4) -0.0004(3) 0.0009(3) -0.0001(3) N3 0.0095(5) 0.0125(5) 0.0140(4) 0.0008(3) 0.0019(3) -0.0005(4) N4 0.0105(5) 0.0201(5) 0.0154(4) 0.0024(3) 0.0008(3) 0.0014(4) O1 0.0135(4) 0.0171(4) 0.0151(4) 0.0025(3) -0.0018(3) -0.0007(3) P1 0.0074(2) 0.0105(2) 0.0124(2) 0.00041(8) 0.00051(8) -0.00073(9) _refine_ls_extinction_coef 110(20) _refine_ls_extinction_method 'Larson (1970), Equation 22' 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 . C14 . 1.5307(15) yes C1 . C15 . 1.5333(14) yes C1 . C16 . 1.5431(14) yes C1 . P1 . 1.8289(10) yes C2 . N1 . 1.3178(13) yes C2 . N2 . 1.3754(13) yes C2 . P1 . 1.8071(9) yes C3 . C4 . 1.3583(15) yes C3 . N1 . 1.3788(13) yes C3 . H31 . 0.972 no C4 . N2 . 1.3823(13) yes C4 . H41 . 0.955 no C5 . C6 . 1.3941(14) yes C5 . C10 . 1.4007(14) yes C5 . N2 . 1.4302(13) yes C6 . C7 . 1.3803(15) yes C6 . H61 . 0.964 no C7 . C8 . 1.3888(16) yes C7 . H71 . 0.981 no C8 . C9 . 1.3793(15) yes C8 . H81 . 0.973 no C9 . C10 . 1.3959(14) yes C9 . H91 . 0.956 no C10 . N3 . 1.4290(13) yes C11 . C12 . 1.3526(16) yes C11 . N3 . 1.3839(14) yes C11 . H111 . 0.965 no C12 . N4 . 1.3768(14) yes C12 . H121 . 0.970 no C13 . N3 . 1.3811(14) yes C13 . N4 . 1.3229(13) yes C13 . P1 . 1.8033(11) yes C14 . H141 . 1.026 no C14 . H142 . 0.993 no C14 . H143 . 0.982 no C15 . H151 . 0.985 no C15 . H152 . 0.990 no C15 . H153 . 0.977 no C16 . H161 . 0.984 no C16 . H162 . 0.977 no C16 . H163 . 0.998 no O1 . P1 . 1.4848(7) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C14 . C1 . C15 . 110.02(9) yes C14 . C1 . C16 . 108.95(8) yes C15 . C1 . C16 . 110.94(8) yes C14 . C1 . P1 . 107.11(7) yes C15 . C1 . P1 . 112.54(7) yes C16 . C1 . P1 . 107.12(7) yes N1 . C2 . N2 . 111.73(8) yes N1 . C2 . P1 . 127.47(7) yes N2 . C2 . P1 . 120.79(7) yes C4 . C3 . N1 . 110.75(8) yes C4 . C3 . H31 . 125.8 no N1 . C3 . H31 . 123.4 no C3 . C4 . N2 . 106.06(8) yes C3 . C4 . H41 . 128.9 no N2 . C4 . H41 . 125.0 no C6 . C5 . C10 . 119.26(9) yes C6 . C5 . N2 . 116.66(9) yes C10 . C5 . N2 . 124.02(9) yes C5 . C6 . C7 . 121.32(9) yes C5 . C6 . H61 . 119.2 no C7 . C6 . H61 . 119.5 no C6 . C7 . C8 . 119.13(9) yes C6 . C7 . H71 . 119.9 no C8 . C7 . H71 . 121.0 no C7 . C8 . C9 . 120.40(9) yes C7 . C8 . H81 . 120.1 no C9 . C8 . H81 . 119.5 no C8 . C9 . C10 . 120.81(9) yes C8 . C9 . H91 . 120.3 no C10 . C9 . H91 . 118.9 no C5 . C10 . C9 . 118.97(9) yes C5 . C10 . N3 . 123.59(9) yes C9 . C10 . N3 . 117.36(8) yes C12 . C11 . N3 . 106.63(9) yes C12 . C11 . H111 . 129.4 no N3 . C11 . H111 . 124.0 no C11 . C12 . N4 . 110.81(9) yes C11 . C12 . H121 . 125.1 no N4 . C12 . H121 . 123.9 no N3 . C13 . N4 . 111.71(9) yes N3 . C13 . P1 . 121.75(8) yes N4 . C13 . P1 . 126.36(8) yes C1 . C14 . H141 . 111.3 no C1 . C14 . H142 . 108.3 no H141 . C14 . H142 . 108.8 no C1 . C14 . H143 . 109.4 no H141 . C14 . H143 . 110.7 no H142 . C14 . H143 . 108.2 no C1 . C15 . H151 . 108.2 no C1 . C15 . H152 . 105.6 no H151 . C15 . H152 . 110.3 no C1 . C15 . H153 . 110.8 no H151 . C15 . H153 . 112.5 no H152 . C15 . H153 . 109.2 no C1 . C16 . H161 . 108.9 no C1 . C16 . H162 . 106.5 no H161 . C16 . H162 . 110.1 no C1 . C16 . H163 . 110.5 no H161 . C16 . H163 . 111.7 no H162 . C16 . H163 . 109.0 no C3 . N1 . C2 . 105.22(8) yes C5 . N2 . C4 . 123.40(8) yes C5 . N2 . C2 . 130.09(8) yes C4 . N2 . C2 . 106.24(8) yes C10 . N3 . C11 . 124.32(9) yes C10 . N3 . C13 . 129.87(9) yes C11 . N3 . C13 . 105.68(9) yes C12 . N4 . C13 . 105.17(9) yes C1 . P1 . C2 . 108.34(5) yes C1 . P1 . C13 . 108.07(5) yes C2 . P1 . C13 . 98.70(4) yes C1 . P1 . O1 . 115.27(4) yes C2 . P1 . O1 . 112.84(4) yes C13 . P1 . O1 . 112.26(4) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C4 . H41 . N1 3_545 170.70(3) 0.955 2.439 3.3848(14) yes C7 . H71 . O1 3_545 138.50(3) 0.981 2.535 3.3337(14) yes C9 . H91 . O1 2_666 146.62(3) 0.956 2.463 3.3031(14) yes C14 . H143 . N1 . 129.86(3) 0.982 2.592 3.3079(14) yes C15 . H151 . N4 . 131.89(3) 0.985 2.519 3.2596(14) yes C15 . H153 . N1 . 129.84(3) 0.977 2.554 3.2667(14) yes C16 . H161 . N4 . 130.72(3) 0.984 2.555 3.2825(14) yes _iucr_refine_instruction_details_constraints ; # # Punched on 10/01/12 at 11:23:22 # #LIST 12 BLOCK SCALE X'S, U'S CONT EXTPARAM RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 14,X'S) H ( 141,X'S) H ( 142,X'S) H ( 143,X'S) RIDE C ( 15,X'S) H ( 151,X'S) H ( 152,X'S) H ( 153,X'S) RIDE C ( 16,X'S) H ( 161,X'S) H ( 162,X'S) H ( 163,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 10/01/12 at 11:23:22 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _database_code_depnum_ccdc_archive 'CCDC 932384' ####################################################################### # # 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_2 #TrackingRef 'CIFcarine120912.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 15.7038(3) _cell_length_b 25.3224(3) _cell_length_c 13.7018(2) _cell_angle_alpha 90 _cell_angle_beta 107.6226(18) _cell_angle_gamma 90 _cell_volume 5192.91(15) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc ' 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 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 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' P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 _chemical_formula_sum 'C20 H23 F6 N4 O6 P S2 ' _chemical_formula_moiety 'C18 H23 N4 P, 2(C F3 O3 S) ' _chemical_compound_source ? _chemical_formula_weight 624.52 _cell_measurement_reflns_used 19220 _cell_measurement_theta_min 3 _cell_measurement_theta_max 61 _cell_measurement_temperature 100 _exptl_crystal_description planar _exptl_crystal_colour colorless _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.250 _exptl_crystal_density_diffrn 1.598 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 2560 _exptl_absorpt_coefficient_mu 3.256 # Sheldrick geometric approximatio 0.52 0.72 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis, (Oxford Diffraction, 2002)' _exptl_absorpt_correction_T_min 0.50 _exptl_absorpt_correction_T_max 0.72 _diffrn_measurement_device_type 'Oxford Diffraction Gemini' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Gemini, (Oxford Diffraction, 2006)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _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 100 _diffrn_reflns_number 40366 _reflns_number_total 7866 _diffrn_reflns_av_R_equivalents 0.032 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 7866 # Theoretical number of reflections is about 15736 _diffrn_reflns_theta_min 3.430 _diffrn_reflns_theta_max 60.681 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 60.681 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -17 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 28 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.41 _refine_diff_density_max 0.76 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 7045 _refine_ls_number_restraints 0 _refine_ls_number_parameters 703 _oxford_refine_ls_R_factor_ref 0.0334 _refine_ls_wR_factor_ref 0.0337 _refine_ls_goodness_of_fit_ref 1.1819 _refine_ls_shift/su_max 0.0008503 _refine_ls_shift/su_mean 0.0000446 # The values computed from all data _oxford_reflns_number_all 7825 _refine_ls_R_factor_all 0.0378 _refine_ls_wR_factor_all 0.0356 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 7045 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_gt 0.0337 # 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: 4.67 -1.16 3.20 ; # 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 0.62960(10) 0.10838(6) 0.39266(12) 0.0183 1.0000 Uani . . . . . . N2 N 0.76978(10) 0.11432(6) 0.40726(11) 0.0163 1.0000 Uani . . . . . . N3 N 0.86541(10) 0.20535(6) 0.52066(11) 0.0155 1.0000 Uani . . . . . . N4 N 0.78031(10) 0.26046(6) 0.56696(11) 0.0160 1.0000 Uani . . . . . . N5 N 0.11041(10) 0.11149(6) -0.08651(11) 0.0148 1.0000 Uani . . . . . . N6 N 0.24610(10) 0.11107(6) -0.09274(11) 0.0150 1.0000 Uani . . . . . . N7 N 0.35858(10) 0.19827(6) 0.01298(11) 0.0159 1.0000 Uani . . . . . . N8 N 0.28854(10) 0.25548(6) 0.07610(12) 0.0173 1.0000 Uani . . . . . . O1 O 0.73388(13) -0.09204(6) 0.49382(14) 0.0496 1.0000 Uani . . . . . . O2 O 0.74884(12) -0.03659(7) 0.35635(14) 0.0493 1.0000 Uani . . . . . . O3 O 0.71188(12) 0.00280(6) 0.49571(13) 0.0416 1.0000 Uani . . . . . . O4 O 0.54928(9) 0.22893(5) 0.40917(10) 0.0255 1.0000 Uani . . . . . . O5 O 0.51444(10) 0.19975(5) 0.23263(10) 0.0287 1.0000 Uani . . . . . . O6 O 0.66458(9) 0.22978(5) 0.32497(11) 0.0257 1.0000 Uani . . . . . . O7 O 0.78372(10) 0.50188(5) 0.52873(11) 0.0292 1.0000 Uani . . . . . . O8 O 0.76906(10) 0.41496(6) 0.59577(12) 0.0361 1.0000 Uani . . . . . . O9 O 0.84298(10) 0.42502(6) 0.46619(11) 0.0356 1.0000 Uani . . . . . . O10 O 1.00791(10) 0.29368(5) 0.26082(11) 0.0284 1.0000 Uani . . . . . . O11 O 1.06898(9) 0.26257(5) 0.43590(10) 0.0227 1.0000 Uani . . . . . . O12 O 1.16561(9) 0.27100(6) 0.32823(11) 0.0283 1.0000 Uani . . . . . . F1 F 0.55648(9) -0.01326(5) 0.30774(12) 0.0506 1.0000 Uani . . . . . . F2 F 0.54608(13) -0.05878(13) 0.43425(17) 0.1216 1.0000 Uani . . . . . . F3 F 0.57771(15) -0.09550(6) 0.31231(16) 0.0901 1.0000 Uani . . . . . . F4 F 0.45244(8) 0.30709(5) 0.26655(10) 0.0328 1.0000 Uani . . . . . . F5 F 0.54549(8) 0.30804(4) 0.17856(8) 0.0283 1.0000 Uani . . . . . . F6 F 0.58747(8) 0.33416(5) 0.33509(9) 0.0327 1.0000 Uani . . . . . . F7 F 0.91575(9) 0.47699(5) 0.73266(8) 0.0353 1.0000 Uani . . . . . . F8 F 0.97878(8) 0.48947(5) 0.61576(9) 0.0320 1.0000 Uani . . . . . . F9 F 0.96672(9) 0.41082(5) 0.66858(11) 0.0402 1.0000 Uani . . . . . . F10 F 0.96661(8) 0.18316(5) 0.28980(9) 0.0311 1.0000 Uani . . . . . . F11 F 1.05157(8) 0.19025(4) 0.19276(9) 0.0285 1.0000 Uani . . . . . . F12 F 1.10535(8) 0.16147(4) 0.34698(9) 0.0326 1.0000 Uani . . . . . . C1 C 0.77511(12) 0.11856(7) 0.68858(13) 0.0162 1.0000 Uani . . . . . . C2 C 0.70900(12) 0.12266(7) 0.45715(14) 0.0154 1.0000 Uani . . . . . . C3 C 0.64064(13) 0.09214(7) 0.30182(14) 0.0215 1.0000 Uani . . . . . . C4 C 0.72737(13) 0.09555(7) 0.31016(14) 0.0206 1.0000 Uani . . . . . . C5 C 0.86529(12) 0.11540(7) 0.45102(13) 0.0164 1.0000 Uani . . . . . . C6 C 0.91213(13) 0.07111(7) 0.43684(15) 0.0203 1.0000 Uani . . . . . . C7 C 1.00432(13) 0.07048(8) 0.47505(15) 0.0234 1.0000 Uani . . . . . . C8 C 1.04962(13) 0.11307(8) 0.52976(15) 0.0227 1.0000 Uani . . . . . . C9 C 1.00299(13) 0.15674(7) 0.54606(14) 0.0193 1.0000 Uani . . . . . . C10 C 0.91046(12) 0.15831(7) 0.50575(14) 0.0161 1.0000 Uani . . . . . . C11 C 0.89561(13) 0.25536(7) 0.50877(15) 0.0202 1.0000 Uani . . . . . . C12 C 0.84224(13) 0.28958(7) 0.53795(14) 0.0200 1.0000 Uani . . . . . . C13 C 0.79448(12) 0.20894(7) 0.55649(13) 0.0141 1.0000 Uani . . . . . . C14 C 0.85738(13) 0.08739(8) 0.68561(14) 0.0203 1.0000 Uani . . . . . . C15 C 0.70322(13) 0.08045(7) 0.70100(15) 0.0201 1.0000 Uani . . . . . . C16 C 0.79878(13) 0.15945(7) 0.77545(14) 0.0200 1.0000 Uani . . . . . . C17 C 0.54579(13) 0.10554(8) 0.41802(16) 0.0247 1.0000 Uani . . . . . . C18 C 0.70950(13) 0.28353(8) 0.60338(16) 0.0224 1.0000 Uani . . . . . . C19 C 0.28365(12) 0.10940(7) 0.19390(14) 0.0179 1.0000 Uani . . . . . . C20 C 0.19515(12) 0.12201(7) -0.03148(13) 0.0147 1.0000 Uani . . . . . . C21 C 0.10818(13) 0.09422(7) -0.18193(14) 0.0178 1.0000 Uani . . . . . . C22 C 0.19265(13) 0.09376(7) -0.18623(14) 0.0179 1.0000 Uani . . . . . . C23 C 0.34187(12) 0.10902(7) -0.06333(13) 0.0157 1.0000 Uani . . . . . . C24 C 0.38128(13) 0.06420(7) -0.08871(14) 0.0198 1.0000 Uani . . . . . . C25 C 0.47295(13) 0.06057(8) -0.06283(15) 0.0233 1.0000 Uani . . . . . . C26 C 0.52674(13) 0.10081(8) -0.00873(15) 0.0232 1.0000 Uani . . . . . . C27 C 0.48789(13) 0.14555(8) 0.01706(14) 0.0199 1.0000 Uani . . . . . . C28 C 0.39546(12) 0.15004(7) -0.01120(14) 0.0166 1.0000 Uani . . . . . . C29 C 0.38773(13) 0.24760(7) -0.00577(14) 0.0195 1.0000 Uani . . . . . . C30 C 0.34308(13) 0.28299(8) 0.03353(15) 0.0212 1.0000 Uani . . . . . . C31 C 0.29731(12) 0.20353(7) 0.06322(13) 0.0150 1.0000 Uani . . . . . . C32 C 0.36099(13) 0.07835(8) 0.17673(15) 0.0212 1.0000 Uani . . . . . . C33 C 0.31520(13) 0.14512(8) 0.28892(14) 0.0234 1.0000 Uani . . . . . . C34 C 0.21132(13) 0.07111(8) 0.20540(15) 0.0224 1.0000 Uani . . . . . . C35 C 0.03150(12) 0.11489(8) -0.05030(15) 0.0204 1.0000 Uani . . . . . . C36 C 0.23023(14) 0.28048(8) 0.12908(16) 0.0251 1.0000 Uani . . . . . . C37 C 0.59118(17) -0.05250(10) 0.3703(2) 0.0420 1.0000 Uani . . . . . . C38 C 0.53763(13) 0.29880(8) 0.27123(15) 0.0220 1.0000 Uani . . . . . . C39 C 0.92466(14) 0.45694(8) 0.64606(15) 0.0234 1.0000 Uani . . . . . . C40 C 1.04887(13) 0.19589(8) 0.28877(15) 0.0210 1.0000 Uani . . . . . . S1 S 1.07602(3) 0.263554(17) 0.33289(3) 0.0167 1.0000 Uani . . . . . . S2 S 0.57047(3) 0.231613(17) 0.31390(3) 0.0171 1.0000 Uani . . . . . . S3 S 0.81719(3) 0.449348(17) 0.54746(3) 0.0189 1.0000 Uani . . . . . . S4 S 0.70950(3) -0.043952(19) 0.43765(4) 0.0243 1.0000 Uani . . . . . . P1 P 0.71628(3) 0.159019(17) 0.57472(3) 0.0137 1.0000 Uani . . . . . . P2 P 0.22060(3) 0.155756(18) 0.09168(3) 0.0142 1.0000 Uani . . . . . . H31 H 0.5942 0.0809 0.2457 0.0246 1.0000 Uiso R . . . . . H41 H 0.7553 0.0876 0.2614 0.0251 1.0000 Uiso R . . . . . H61 H 0.8805 0.0419 0.4011 0.0246 1.0000 Uiso R . . . . . H71 H 1.0363 0.0411 0.4643 0.0281 1.0000 Uiso R . . . . . H81 H 1.1118 0.1127 0.5563 0.0267 1.0000 Uiso R . . . . . H91 H 1.0331 0.1851 0.5854 0.0230 1.0000 Uiso R . . . . . H111 H 0.9443 0.2623 0.4843 0.0233 1.0000 Uiso R . . . . . H121 H 0.8443 0.3268 0.5387 0.0237 1.0000 Uiso R . . . . . H143 H 0.9044 0.1107 0.6814 0.0304 1.0000 Uiso R . . . . . H142 H 0.8788 0.0672 0.7477 0.0301 1.0000 Uiso R . . . . . H141 H 0.8435 0.0640 0.6284 0.0302 1.0000 Uiso R . . . . . H151 H 0.6504 0.1004 0.7007 0.0292 1.0000 Uiso R . . . . . H152 H 0.7256 0.0619 0.7655 0.0293 1.0000 Uiso R . . . . . H153 H 0.6876 0.0549 0.6454 0.0303 1.0000 Uiso R . . . . . H163 H 0.7477 0.1809 0.7725 0.0296 1.0000 Uiso R . . . . . H162 H 0.8469 0.1819 0.7693 0.0291 1.0000 Uiso R . . . . . H161 H 0.8168 0.1408 0.8388 0.0297 1.0000 Uiso R . . . . . H173 H 0.4988 0.1144 0.3584 0.0377 1.0000 Uiso R . . . . . H172 H 0.5474 0.1303 0.4714 0.0368 1.0000 Uiso R . . . . . H171 H 0.5381 0.0708 0.4388 0.0372 1.0000 Uiso R . . . . . H181 H 0.6534 0.2675 0.5661 0.0344 1.0000 Uiso R . . . . . H182 H 0.7223 0.2771 0.6742 0.0341 1.0000 Uiso R . . . . . H183 H 0.7083 0.3205 0.5904 0.0345 1.0000 Uiso R . . . . . H211 H 0.0557 0.0850 -0.2333 0.0215 1.0000 Uiso R . . . . . H221 H 0.2130 0.0838 -0.2405 0.0215 1.0000 Uiso R . . . . . H241 H 0.3460 0.0366 -0.1231 0.0235 1.0000 Uiso R . . . . . H251 H 0.4987 0.0302 -0.0810 0.0285 1.0000 Uiso R . . . . . H261 H 0.5897 0.0979 0.0104 0.0284 1.0000 Uiso R . . . . . H271 H 0.5234 0.1726 0.0545 0.0236 1.0000 Uiso R . . . . . H291 H 0.4303 0.2538 -0.0390 0.0230 1.0000 Uiso R . . . . . H301 H 0.3472 0.3195 0.0345 0.0258 1.0000 Uiso R . . . . . H323 H 0.3416 0.0574 0.1164 0.0311 1.0000 Uiso R . . . . . H322 H 0.4083 0.1015 0.1720 0.0319 1.0000 Uiso R . . . . . H321 H 0.3856 0.0549 0.2327 0.0321 1.0000 Uiso R . . . . . H331 H 0.2662 0.1660 0.2964 0.0343 1.0000 Uiso R . . . . . H332 H 0.3630 0.1678 0.2831 0.0342 1.0000 Uiso R . . . . . H333 H 0.3368 0.1224 0.3478 0.0353 1.0000 Uiso R . . . . . H343 H 0.1610 0.0905 0.2126 0.0340 1.0000 Uiso R . . . . . H342 H 0.2369 0.0498 0.2664 0.0340 1.0000 Uiso R . . . . . H341 H 0.1924 0.0480 0.1465 0.0341 1.0000 Uiso R . . . . . H353 H -0.0170 0.1289 -0.1048 0.0317 1.0000 Uiso R . . . . . H352 H 0.0437 0.1375 0.0078 0.0318 1.0000 Uiso R . . . . . H351 H 0.0161 0.0802 -0.0341 0.0319 1.0000 Uiso R . . . . . H361 H 0.1725 0.2656 0.1045 0.0397 1.0000 Uiso R . . . . . H362 H 0.2542 0.2746 0.2000 0.0393 1.0000 Uiso R . . . . . H363 H 0.2280 0.3168 0.1146 0.0391 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 0.0181(8) 0.0151(8) 0.0189(8) 0.0012(6) 0.0015(7) -0.0009(6) N2 0.0188(8) 0.0127(7) 0.0166(8) -0.0007(6) 0.0041(7) 0.0000(6) N3 0.0171(8) 0.0124(8) 0.0172(8) -0.0005(6) 0.0055(6) -0.0008(6) N4 0.0169(8) 0.0147(8) 0.0158(8) -0.0001(6) 0.0041(6) 0.0017(6) N5 0.0128(8) 0.0123(7) 0.0181(8) 0.0025(6) 0.0028(6) 0.0004(6) N6 0.0155(8) 0.0132(7) 0.0163(8) 0.0004(6) 0.0050(6) 0.0007(6) N7 0.0151(8) 0.0146(8) 0.0185(8) -0.0002(6) 0.0058(6) -0.0003(6) N8 0.0173(8) 0.0161(8) 0.0180(8) -0.0020(6) 0.0046(6) -0.0014(6) O1 0.0602(12) 0.0269(9) 0.0547(11) 0.0108(8) 0.0069(9) 0.0007(8) O2 0.0553(11) 0.0550(11) 0.0503(11) -0.0003(9) 0.0349(9) 0.0081(9) O3 0.0525(10) 0.0279(8) 0.0384(9) -0.0111(7) 0.0046(8) 0.0042(7) O4 0.0283(8) 0.0278(7) 0.0239(7) 0.0057(6) 0.0131(6) 0.0055(6) O5 0.0362(8) 0.0226(7) 0.0240(7) -0.0007(6) 0.0039(6) -0.0051(6) O6 0.0216(7) 0.0277(8) 0.0297(8) 0.0047(6) 0.0107(6) 0.0060(6) O7 0.0334(8) 0.0184(7) 0.0292(8) -0.0001(6) -0.0004(6) 0.0062(6) O8 0.0352(9) 0.0369(9) 0.0385(9) 0.0066(7) 0.0144(7) -0.0101(7) O9 0.0365(9) 0.0409(9) 0.0315(8) -0.0172(7) 0.0136(7) 0.0000(7) O10 0.0345(8) 0.0207(7) 0.0270(8) 0.0017(6) 0.0050(6) 0.0042(6) O11 0.0277(7) 0.0227(7) 0.0206(7) -0.0034(6) 0.0116(6) -0.0035(6) O12 0.0253(8) 0.0307(8) 0.0339(8) -0.0075(6) 0.0163(6) -0.0093(6) F1 0.0372(8) 0.0323(8) 0.0672(10) 0.0012(7) -0.0071(7) -0.0029(6) F2 0.0472(11) 0.236(3) 0.0902(15) 0.0490(18) 0.0339(11) -0.0304(15) F3 0.1155(17) 0.0286(9) 0.0888(14) -0.0055(9) -0.0254(12) -0.0288(9) F4 0.0246(6) 0.0336(7) 0.0429(7) 0.0122(6) 0.0143(5) 0.0123(5) F5 0.0349(7) 0.0270(6) 0.0250(6) 0.0086(5) 0.0122(5) 0.0005(5) F6 0.0419(7) 0.0214(6) 0.0377(7) -0.0073(5) 0.0162(6) -0.0043(5) F7 0.0484(8) 0.0364(7) 0.0176(6) 0.0016(5) 0.0048(5) 0.0033(6) F8 0.0279(6) 0.0287(6) 0.0376(7) 0.0023(5) 0.0074(5) -0.0060(5) F9 0.0380(7) 0.0218(6) 0.0534(8) 0.0088(6) 0.0027(6) 0.0107(5) F10 0.0300(7) 0.0283(6) 0.0400(7) -0.0100(5) 0.0182(6) -0.0128(5) F11 0.0381(7) 0.0266(6) 0.0250(6) -0.0089(5) 0.0158(5) -0.0040(5) F12 0.0430(7) 0.0195(6) 0.0382(7) 0.0060(5) 0.0165(6) 0.0094(5) C1 0.0169(9) 0.0171(9) 0.0138(9) 0.0022(7) 0.0034(7) 0.0006(7) C2 0.0164(9) 0.0116(9) 0.0171(9) 0.0024(7) 0.0035(7) -0.0002(7) C3 0.0262(11) 0.0182(10) 0.0156(9) -0.0011(8) -0.0004(8) -0.0014(8) C4 0.0295(11) 0.0159(9) 0.0160(10) -0.0010(8) 0.0065(8) 0.0002(8) C5 0.0198(10) 0.0166(9) 0.0149(9) 0.0021(7) 0.0084(8) 0.0006(8) C6 0.0281(11) 0.0144(9) 0.0217(10) 0.0004(8) 0.0127(8) 0.0004(8) C7 0.0262(11) 0.0181(10) 0.0307(11) 0.0035(8) 0.0157(9) 0.0070(8) C8 0.0183(10) 0.0233(10) 0.0294(11) 0.0058(9) 0.0113(8) 0.0026(8) C9 0.0192(10) 0.0186(10) 0.0213(10) 0.0009(8) 0.0081(8) -0.0017(8) C10 0.0193(10) 0.0148(9) 0.0168(9) 0.0024(7) 0.0093(8) 0.0029(7) C11 0.0236(10) 0.0162(10) 0.0230(10) 0.0003(8) 0.0103(8) -0.0025(8) C12 0.0244(10) 0.0123(9) 0.0230(10) -0.0007(7) 0.0068(8) -0.0012(8) C13 0.0161(9) 0.0131(9) 0.0117(9) -0.0005(7) 0.0025(7) 0.0012(7) C14 0.0197(10) 0.0218(10) 0.0181(10) 0.0053(8) 0.0040(8) 0.0042(8) C15 0.0220(10) 0.0179(10) 0.0212(10) 0.0028(8) 0.0077(8) -0.0002(8) C16 0.0240(10) 0.0186(10) 0.0164(9) 0.0003(8) 0.0048(8) 0.0001(8) C17 0.0163(10) 0.0257(11) 0.0288(11) 0.0009(9) 0.0020(8) -0.0041(8) C18 0.0235(10) 0.0173(10) 0.0287(11) -0.0025(8) 0.0113(9) 0.0043(8) C19 0.0165(9) 0.0199(10) 0.0157(9) 0.0005(8) 0.0026(7) -0.0010(8) C20 0.0149(9) 0.0117(9) 0.0167(9) 0.0022(7) 0.0033(7) -0.0002(7) C21 0.0198(10) 0.0137(9) 0.0167(9) 0.0010(7) 0.0005(8) -0.0016(7) C22 0.0241(10) 0.0136(9) 0.0148(9) -0.0009(7) 0.0044(8) 0.0002(8) C23 0.0151(9) 0.0176(9) 0.0150(9) 0.0034(7) 0.0057(7) 0.0010(7) C24 0.0233(10) 0.0167(10) 0.0211(10) -0.0003(8) 0.0094(8) 0.0010(8) C25 0.0258(11) 0.0202(10) 0.0279(11) 0.0026(8) 0.0141(9) 0.0066(8) C26 0.0178(10) 0.0285(11) 0.0255(11) 0.0044(9) 0.0097(8) 0.0035(8) C27 0.0174(10) 0.0228(10) 0.0202(10) 0.0008(8) 0.0070(8) -0.0015(8) C28 0.0189(10) 0.0165(9) 0.0162(9) 0.0013(7) 0.0080(8) 0.0015(7) C29 0.0202(10) 0.0161(9) 0.0223(10) 0.0011(8) 0.0068(8) -0.0048(8) C30 0.0230(10) 0.0161(10) 0.0242(10) 0.0007(8) 0.0067(8) -0.0028(8) C31 0.0138(9) 0.0152(9) 0.0151(9) -0.0008(7) 0.0029(7) -0.0005(7) C32 0.0189(10) 0.0239(10) 0.0196(10) 0.0022(8) 0.0039(8) 0.0032(8) C33 0.0230(10) 0.0286(11) 0.0180(10) -0.0023(8) 0.0053(8) -0.0017(8) C34 0.0221(10) 0.0216(10) 0.0225(10) 0.0044(8) 0.0053(8) -0.0015(8) C35 0.0146(9) 0.0221(10) 0.0245(10) -0.0009(8) 0.0060(8) -0.0019(8) C36 0.0253(11) 0.0193(10) 0.0343(12) -0.0069(9) 0.0145(9) 0.0018(8) C37 0.0436(14) 0.0343(14) 0.0478(15) 0.0056(12) 0.0135(12) -0.0137(11) C38 0.0226(10) 0.0210(10) 0.0243(10) 0.0018(8) 0.0101(8) 0.0004(8) C39 0.0293(11) 0.0159(10) 0.0247(11) 0.0044(8) 0.0076(9) 0.0044(8) C40 0.0245(10) 0.0189(10) 0.0228(10) -0.0030(8) 0.0120(8) -0.0019(8) S1 0.0187(2) 0.0144(2) 0.0185(2) -0.00180(17) 0.00775(18) -0.00188(17) S2 0.0181(2) 0.0167(2) 0.0169(2) 0.00199(18) 0.00590(18) 0.00131(18) S3 0.0232(2) 0.0137(2) 0.0206(2) -0.00117(18) 0.00786(19) 0.00001(18) S4 0.0328(3) 0.0170(2) 0.0254(3) -0.00233(19) 0.0123(2) 0.0030(2) P1 0.0129(2) 0.0136(2) 0.0145(2) 0.00113(18) 0.00413(18) 0.00086(17) P2 0.0127(2) 0.0147(2) 0.0154(2) -0.00049(18) 0.00467(18) -0.00036(17) _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 N1 . C2 . 1.341(2) yes N1 . C3 . 1.371(3) yes N1 . C17 . 1.461(3) yes N2 . C2 . 1.348(2) yes N2 . C4 . 1.379(2) yes N2 . C5 . 1.437(2) yes N3 . C10 . 1.431(2) yes N3 . C11 . 1.379(2) yes N3 . C13 . 1.349(2) yes N4 . C12 . 1.372(2) yes N4 . C13 . 1.338(2) yes N4 . C18 . 1.471(2) yes N5 . C20 . 1.343(2) yes N5 . C21 . 1.369(2) yes N5 . C35 . 1.470(2) yes N6 . C20 . 1.352(2) yes N6 . C22 . 1.374(2) yes N6 . C23 . 1.435(2) yes N7 . C28 . 1.433(2) yes N7 . C29 . 1.381(2) yes N7 . C31 . 1.348(2) yes N8 . C30 . 1.364(2) yes N8 . C31 . 1.340(2) yes N8 . C36 . 1.473(2) yes O1 . S4 . 1.4295(17) yes O2 . S4 . 1.4403(17) yes O3 . S4 . 1.4204(16) yes O4 . S2 . 1.4431(14) yes O5 . S2 . 1.4395(14) yes O6 . S2 . 1.4399(14) yes O7 . S3 . 1.4248(14) yes O8 . S3 . 1.4390(15) yes O9 . S3 . 1.4340(15) yes O10 . S1 . 1.4359(15) yes O11 . S1 . 1.4489(14) yes O12 . S1 . 1.4398(14) yes F1 . C37 . 1.318(3) yes F2 . C37 . 1.293(3) yes F3 . C37 . 1.327(3) yes F4 . C38 . 1.336(2) yes F5 . C38 . 1.333(2) yes F6 . C38 . 1.329(2) yes F7 . C39 . 1.336(2) yes F8 . C39 . 1.337(2) yes F9 . C39 . 1.331(2) yes F10 . C40 . 1.336(2) yes F11 . C40 . 1.337(2) yes F12 . C40 . 1.324(2) yes C1 . C14 . 1.525(3) yes C1 . C15 . 1.533(3) yes C1 . C16 . 1.536(3) yes C1 . P1 . 1.8613(18) yes C2 . P1 . 1.8288(18) yes C3 . C4 . 1.335(3) yes C3 . H31 . 0.930 no C4 . H41 . 0.925 no C5 . C6 . 1.387(3) yes C5 . C10 . 1.387(3) yes C6 . C7 . 1.383(3) yes C6 . H61 . 0.941 no C7 . C8 . 1.381(3) yes C7 . H71 . 0.933 no C8 . C9 . 1.381(3) yes C8 . H81 . 0.934 no C9 . C10 . 1.390(3) yes C9 . H91 . 0.936 no C11 . C12 . 1.348(3) yes C11 . H111 . 0.939 no C12 . H121 . 0.944 no C13 . P1 . 1.8315(18) yes C14 . H143 . 0.961 no C14 . H142 . 0.962 no C14 . H141 . 0.954 no C15 . H151 . 0.970 no C15 . H152 . 0.968 no C15 . H153 . 0.972 no C16 . H163 . 0.960 no C16 . H162 . 0.970 no C16 . H161 . 0.953 no C17 . H173 . 0.947 no C17 . H172 . 0.958 no C17 . H171 . 0.944 no C18 . H181 . 0.963 no C18 . H182 . 0.944 no C18 . H183 . 0.951 no C19 . C32 . 1.524(3) yes C19 . C33 . 1.539(3) yes C19 . C34 . 1.537(3) yes C19 . P2 . 1.8656(19) yes C20 . P2 . 1.8247(18) yes C21 . C22 . 1.346(3) yes C21 . H211 . 0.937 no C22 . H221 . 0.929 no C23 . C24 . 1.386(3) yes C23 . C28 . 1.390(3) yes C24 . C25 . 1.377(3) yes C24 . H241 . 0.928 no C25 . C26 . 1.386(3) yes C25 . H251 . 0.937 no C26 . C27 . 1.383(3) yes C26 . H261 . 0.946 no C27 . C28 . 1.389(3) yes C27 . H271 . 0.933 no C29 . C30 . 1.347(3) yes C29 . H291 . 0.930 no C30 . H301 . 0.927 no C31 . P2 . 1.8306(18) yes C32 . H323 . 0.952 no C32 . H322 . 0.964 no C32 . H321 . 0.953 no C33 . H331 . 0.964 no C33 . H332 . 0.967 no C33 . H333 . 0.964 no C34 . H343 . 0.960 no C34 . H342 . 0.973 no C34 . H341 . 0.968 no C35 . H353 . 0.959 no C35 . H352 . 0.951 no C35 . H351 . 0.954 no C36 . H361 . 0.945 no C36 . H362 . 0.942 no C36 . H363 . 0.940 no C37 . S4 . 1.820(3) yes C38 . S2 . 1.822(2) yes C39 . S3 . 1.825(2) yes C40 . S1 . 1.8240(19) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . N1 . C3 . 109.33(16) yes C2 . N1 . C17 . 125.54(16) yes C3 . N1 . C17 . 124.87(16) yes C2 . N2 . C4 . 109.50(15) yes C2 . N2 . C5 . 126.52(15) yes C4 . N2 . C5 . 123.17(15) yes C10 . N3 . C11 . 123.01(15) yes C10 . N3 . C13 . 127.31(15) yes C11 . N3 . C13 . 109.41(15) yes C12 . N4 . C13 . 109.72(15) yes C12 . N4 . C18 . 124.05(15) yes C13 . N4 . C18 . 126.23(15) yes C20 . N5 . C21 . 109.53(15) yes C20 . N5 . C35 . 126.31(15) yes C21 . N5 . C35 . 124.09(15) yes C20 . N6 . C22 . 109.57(15) yes C20 . N6 . C23 . 126.86(15) yes C22 . N6 . C23 . 122.87(15) yes C28 . N7 . C29 . 123.24(15) yes C28 . N7 . C31 . 127.08(15) yes C29 . N7 . C31 . 109.49(15) yes C30 . N8 . C31 . 110.01(15) yes C30 . N8 . C36 . 123.76(16) yes C31 . N8 . C36 . 126.23(15) yes C14 . C1 . C15 . 109.60(15) yes C14 . C1 . C16 . 111.19(15) yes C15 . C1 . C16 . 110.60(15) yes C14 . C1 . P1 . 118.17(13) yes C15 . C1 . P1 . 104.13(12) yes C16 . C1 . P1 . 102.75(12) yes N2 . C2 . N1 . 106.47(15) yes N2 . C2 . P1 . 131.33(14) yes N1 . C2 . P1 . 120.91(13) yes N1 . C3 . C4 . 108.01(17) yes N1 . C3 . H31 . 124.1 no C4 . C3 . H31 . 127.9 no N2 . C4 . C3 . 106.68(17) yes N2 . C4 . H41 . 125.1 no C3 . C4 . H41 . 128.2 no N2 . C5 . C6 . 117.19(16) yes N2 . C5 . C10 . 122.60(16) yes C6 . C5 . C10 . 120.21(17) yes C5 . C6 . C7 . 119.68(18) yes C5 . C6 . H61 . 119.3 no C7 . C6 . H61 . 121.0 no C6 . C7 . C8 . 120.32(18) yes C6 . C7 . H71 . 120.1 no C8 . C7 . H71 . 119.6 no C7 . C8 . C9 . 120.11(18) yes C7 . C8 . H81 . 120.6 no C9 . C8 . H81 . 119.3 no C8 . C9 . C10 . 120.01(18) yes C8 . C9 . H91 . 120.6 no C10 . C9 . H91 . 119.4 no N3 . C10 . C9 . 118.00(16) yes N3 . C10 . C5 . 122.35(16) yes C9 . C10 . C5 . 119.63(17) yes N3 . C11 . C12 . 106.76(17) yes N3 . C11 . H111 . 124.1 no C12 . C11 . H111 . 129.2 no N4 . C12 . C11 . 107.43(16) yes N4 . C12 . H121 . 124.0 no C11 . C12 . H121 . 128.6 no N3 . C13 . N4 . 106.69(15) yes N3 . C13 . P1 . 131.64(13) yes N4 . C13 . P1 . 121.20(13) yes C1 . C14 . H143 . 110.9 no C1 . C14 . H142 . 108.9 no H143 . C14 . H142 . 108.0 no C1 . C14 . H141 . 111.0 no H143 . C14 . H141 . 108.7 no H142 . C14 . H141 . 109.2 no C1 . C15 . H151 . 109.3 no C1 . C15 . H152 . 109.3 no H151 . C15 . H152 . 109.3 no C1 . C15 . H153 . 110.6 no H151 . C15 . H153 . 109.2 no H152 . C15 . H153 . 109.2 no C1 . C16 . H163 . 110.2 no C1 . C16 . H162 . 109.9 no H163 . C16 . H162 . 109.2 no C1 . C16 . H161 . 107.9 no H163 . C16 . H161 . 109.5 no H162 . C16 . H161 . 110.2 no N1 . C17 . H173 . 107.8 no N1 . C17 . H172 . 109.4 no H173 . C17 . H172 . 109.7 no N1 . C17 . H171 . 108.9 no H173 . C17 . H171 . 110.0 no H172 . C17 . H171 . 110.9 no N4 . C18 . H181 . 108.5 no N4 . C18 . H182 . 109.5 no H181 . C18 . H182 . 110.4 no N4 . C18 . H183 . 107.6 no H181 . C18 . H183 . 110.5 no H182 . C18 . H183 . 110.3 no C32 . C19 . C33 . 111.50(15) yes C32 . C19 . C34 . 109.80(16) yes C33 . C19 . C34 . 110.03(16) yes C32 . C19 . P2 . 118.39(13) yes C33 . C19 . P2 . 103.12(13) yes C34 . C19 . P2 . 103.48(12) yes N6 . C20 . N5 . 106.43(15) yes N6 . C20 . P2 . 131.68(13) yes N5 . C20 . P2 . 120.98(13) yes N5 . C21 . C22 . 107.70(16) yes N5 . C21 . H211 . 124.0 no C22 . C21 . H211 . 128.3 no N6 . C22 . C21 . 106.77(16) yes N6 . C22 . H221 . 124.9 no C21 . C22 . H221 . 128.4 no N6 . C23 . C24 . 117.94(16) yes N6 . C23 . C28 . 122.48(16) yes C24 . C23 . C28 . 119.58(17) yes C23 . C24 . C25 . 120.08(18) yes C23 . C24 . H241 . 120.1 no C25 . C24 . H241 . 119.8 no C24 . C25 . C26 . 120.57(18) yes C24 . C25 . H251 . 119.2 no C26 . C25 . H251 . 120.3 no C25 . C26 . C27 . 119.63(18) yes C25 . C26 . H261 . 120.5 no C27 . C26 . H261 . 119.9 no C26 . C27 . C28 . 120.03(18) yes C26 . C27 . H271 . 120.4 no C28 . C27 . H271 . 119.6 no N7 . C28 . C23 . 122.10(16) yes N7 . C28 . C27 . 117.81(16) yes C23 . C28 . C27 . 120.07(17) yes N7 . C29 . C30 . 106.59(17) yes N7 . C29 . H291 . 125.0 no C30 . C29 . H291 . 128.5 no N8 . C30 . C29 . 107.54(17) yes N8 . C30 . H301 . 123.6 no C29 . C30 . H301 . 128.8 no N7 . C31 . N8 . 106.36(15) yes N7 . C31 . P2 . 131.36(13) yes N8 . C31 . P2 . 121.35(13) yes C19 . C32 . H323 . 111.2 no C19 . C32 . H322 . 111.4 no H323 . C32 . H322 . 109.3 no C19 . C32 . H321 . 110.2 no H323 . C32 . H321 . 107.3 no H322 . C32 . H321 . 107.4 no C19 . C33 . H331 . 110.5 no C19 . C33 . H332 . 109.8 no H331 . C33 . H332 . 110.3 no C19 . C33 . H333 . 107.4 no H331 . C33 . H333 . 109.2 no H332 . C33 . H333 . 109.7 no C19 . C34 . H343 . 110.1 no C19 . C34 . H342 . 108.1 no H343 . C34 . H342 . 109.5 no C19 . C34 . H341 . 110.2 no H343 . C34 . H341 . 109.9 no H342 . C34 . H341 . 108.9 no N5 . C35 . H353 . 108.0 no N5 . C35 . H352 . 109.9 no H353 . C35 . H352 . 109.9 no N5 . C35 . H351 . 108.8 no H353 . C35 . H351 . 109.0 no H352 . C35 . H351 . 111.2 no N8 . C36 . H361 . 109.0 no N8 . C36 . H362 . 109.1 no H361 . C36 . H362 . 110.2 no N8 . C36 . H363 . 107.8 no H361 . C36 . H363 . 110.1 no H362 . C36 . H363 . 110.5 no F3 . C37 . F1 . 105.7(2) yes F3 . C37 . F2 . 106.5(2) yes F1 . C37 . F2 . 109.3(2) yes F3 . C37 . S4 . 110.8(2) yes F1 . C37 . S4 . 113.45(16) yes F2 . C37 . S4 . 110.83(19) yes F4 . C38 . F5 . 107.86(16) yes F4 . C38 . F6 . 107.90(16) yes F5 . C38 . F6 . 107.65(15) yes F4 . C38 . S2 . 110.13(13) yes F5 . C38 . S2 . 111.75(13) yes F6 . C38 . S2 . 111.40(13) yes F8 . C39 . F7 . 106.79(16) yes F8 . C39 . F9 . 107.16(16) yes F7 . C39 . F9 . 107.79(16) yes F8 . C39 . S3 . 111.56(13) yes F7 . C39 . S3 . 112.06(14) yes F9 . C39 . S3 . 111.23(14) yes F11 . C40 . F10 . 107.68(15) yes F11 . C40 . F12 . 107.90(15) yes F10 . C40 . F12 . 107.95(15) yes F11 . C40 . S1 . 110.65(13) yes F10 . C40 . S1 . 110.68(13) yes F12 . C40 . S1 . 111.83(13) yes C40 . S1 . O11 . 103.15(8) yes C40 . S1 . O12 . 103.99(9) yes O11 . S1 . O12 . 114.15(8) yes C40 . S1 . O10 . 102.74(9) yes O11 . S1 . O10 . 114.74(8) yes O12 . S1 . O10 . 115.75(9) yes C38 . S2 . O4 . 102.34(8) yes C38 . S2 . O6 . 104.22(9) yes O4 . S2 . O6 . 114.43(8) yes C38 . S2 . O5 . 103.17(9) yes O4 . S2 . O5 . 114.78(9) yes O6 . S2 . O5 . 115.53(9) yes C39 . S3 . O8 . 102.71(9) yes C39 . S3 . O9 . 101.82(9) yes O8 . S3 . O9 . 114.10(10) yes C39 . S3 . O7 . 104.07(9) yes O8 . S3 . O7 . 115.55(10) yes O9 . S3 . O7 . 115.90(9) yes C37 . S4 . O2 . 103.55(12) yes C37 . S4 . O1 . 103.75(11) yes O2 . S4 . O1 . 114.77(11) yes C37 . S4 . O3 . 103.47(11) yes O2 . S4 . O3 . 112.37(11) yes O1 . S4 . O3 . 116.82(11) yes C1 . P1 . C13 . 108.13(8) yes C1 . P1 . C2 . 110.12(8) yes C13 . P1 . C2 . 95.33(8) yes C19 . P2 . C31 . 109.99(8) yes C19 . P2 . C20 . 108.51(8) yes C31 . P2 . C20 . 94.96(8) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C4 . H41 . O8 3_554 155.13(6) 0.925 2.345 3.208(3) yes C11 . H111 . O11 . 168.69(6) 0.939 2.250 3.176(3) yes C15 . H153 . O3 . 154.97(6) 0.972 2.563 3.468(3) yes C16 . H161 . O9 3_555 164.18(6) 0.953 2.358 3.285(3) yes C18 . H181 . O4 . 152.19(5) 0.963 2.475 3.357(3) yes C18 . H182 . O6 3_555 147.58(6) 0.944 2.501 3.336(3) yes C18 . H183 . O8 . 157.52(6) 0.951 2.569 3.467(3) yes C22 . H221 . O2 2_655 162.97(7) 0.929 2.210 3.110(3) yes C27 . H271 . O5 . 121.40(5) 0.933 2.580 3.168(3) yes C29 . H291 . O4 3_554 169.78(6) 0.930 2.233 3.153(3) yes C30 . H301 . O1 4_655 147.75(6) 0.927 2.547 3.368(3) yes C36 . H361 . O11 3_454 136.90(6) 0.945 2.493 3.248(3) yes C36 . H362 . O12 1_455 125.78(6) 0.942 2.552 3.195(3) yes _iucr_refine_instruction_details_constraints ; # # Punched on 13/09/12 at 16:57:23 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 14,X'S) H ( 143,X'S) H ( 142,X'S) H ( 141,X'S) RIDE C ( 15,X'S) H ( 151,X'S) H ( 152,X'S) H ( 153,X'S) RIDE C ( 16,X'S) H ( 163,X'S) H ( 162,X'S) H ( 161,X'S) RIDE C ( 17,X'S) H ( 173,X'S) H ( 172,X'S) H ( 171,X'S) RIDE C ( 18,X'S) H ( 181,X'S) H ( 182,X'S) H ( 183,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 22,X'S) H ( 221,X'S) RIDE C ( 24,X'S) H ( 241,X'S) RIDE C ( 25,X'S) H ( 251,X'S) RIDE C ( 26,X'S) H ( 261,X'S) RIDE C ( 27,X'S) H ( 271,X'S) RIDE C ( 29,X'S) H ( 291,X'S) RIDE C ( 30,X'S) H ( 301,X'S) RIDE C ( 32,X'S) H ( 323,X'S) H ( 322,X'S) H ( 321,X'S) RIDE C ( 33,X'S) H ( 331,X'S) H ( 332,X'S) H ( 333,X'S) RIDE C ( 34,X'S) H ( 343,X'S) H ( 342,X'S) H ( 341,X'S) RIDE C ( 35,X'S) H ( 353,X'S) H ( 352,X'S) H ( 351,X'S) RIDE C ( 36,X'S) H ( 361,X'S) H ( 362,X'S) H ( 363,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 13/09/12 at 16:57:23 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _database_code_depnum_ccdc_archive 'CCDC 932385' ####################################################################### # # 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_3 #TrackingRef 'CIFcarine121211.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 11.3573(2) _cell_length_b 12.6287(3) _cell_length_c 10.6515(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1527.73(5) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n m a ' _symmetry_space_group_name_Hall '-P 2ac 2n ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x,-y+1/2,z -x,y+1/2,-z -x+1/2,-y,z+1/2 x+1/2,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' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C16 H17 N4 P1 # Dc = 1.29 Fooo = 624.00 Mu = 1.79 M = 148.16 # Found Formula = C16 H17 N4 P1 # Dc = 1.29 FOOO = 624.00 Mu = 1.79 M = 148.16 _chemical_formula_sum 'C16 H17 N4 P1' _chemical_formula_moiety 'C16 H17 N4 P1' _chemical_compound_source ? _chemical_formula_weight 296.31 _cell_measurement_reflns_used 21993 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _cell_measurement_temperature 180 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.300 _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.179 # Sheldrick geometric approximatio 0.96 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis, (Oxford Diffraction, 2002)' _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device_type 'Oxford Diffraction XCALIBUR' _diffrn_measurement_device Area _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 'Xcalibur, (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _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 180 _diffrn_reflns_number 29596 _reflns_number_total 1942 _diffrn_reflns_av_R_equivalents 0.026 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 1942 # Theoretical number of reflections is about 3817 _diffrn_reflns_theta_min 3.078 _diffrn_reflns_theta_max 28.470 _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 26.762 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min 0 _reflns_limit_h_max 15 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.26 _refine_diff_density_max 0.59 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 1762 _refine_ls_number_restraints 2 _refine_ls_number_parameters 101 _oxford_refine_ls_R_factor_ref 0.0320 _refine_ls_wR_factor_ref 0.0420 _refine_ls_goodness_of_fit_ref 0.9987 _refine_ls_shift/su_max 0.0010249 _refine_ls_shift/su_mean 0.0000580 # The values computed from all data _oxford_reflns_number_all 1936 _refine_ls_R_factor_all 0.0354 _refine_ls_wR_factor_all 0.0436 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1797 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_gt 0.0422 # 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: 11.3 8.83 9.11 4.25 ; # 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 C1 C 0.51365(13) 0.2500 0.38118(14) 0.0266 1.0000 Uani S T . . . . C2 C 0.71232(8) 0.35906(7) 0.50548(8) 0.0187 1.0000 Uani . . . . . . C3 C 0.79056(10) 0.50748(8) 0.55935(9) 0.0270 1.0000 Uani . . . . . . C4 C 0.75300(9) 0.46278(8) 0.66790(9) 0.0237 1.0000 Uani . . . . . . C5 C 0.63664(8) 0.30520(7) 0.72030(8) 0.0182 1.0000 Uani . . . . . . C6 C 0.56937(8) 0.35888(8) 0.80924(9) 0.0227 1.0000 Uani . . . . . . C7 C 0.50527(8) 0.30472(8) 0.89861(9) 0.0255 1.0000 Uani . . . . . . C8 C 0.43720(15) 0.250000(7) 0.49729(18) 0.0461 1.0000 Uani S T . . . . C9 C 0.48832(12) 0.34839(12) 0.30226(15) 0.0490 1.0000 Uani . . . . . . P1 P 0.67704(3) 0.2500 0.40252(3) 0.0188 1.0000 Uani S T . . . . N1 N 0.76656(8) 0.44296(7) 0.45908(8) 0.0241 1.0000 Uani . . . . . . N2 N 0.70254(7) 0.36756(6) 0.63458(7) 0.0188 1.0000 Uani . . . . . . H31 H 0.8303 0.5734 0.5502 0.0325 1.0000 Uiso R . . . . . H41 H 0.7583 0.4870 0.7515 0.0287 1.0000 Uiso R . . . . . H61 H 0.5681 0.4327 0.8095 0.0286 1.0000 Uiso R . . . . . H71 H 0.4608 0.3420 0.9598 0.0319 1.0000 Uiso R . . . . . H92 H 0.5410 0.3485 0.2288 0.0726 1.0000 Uiso R . . . . . H93 H 0.5051 0.4128 0.3498 0.0734 1.0000 Uiso R . . . . . H91 H 0.4065 0.3463 0.2770 0.0720 1.0000 Uiso R . . . . . H81 H 0.4532 0.3101 0.5448 0.0557 1.0000 Uiso R . . . . . H82 H 0.3583 0.2500 0.4738 0.0557 1.0000 Uiso RS . . . . . 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 0.0240(6) 0.0296(7) 0.0263(6) 0.0000 -0.0071(5) 0.0000 C2 0.0217(4) 0.0198(4) 0.0145(4) 0.0015(3) 0.0000(3) 0.0004(3) C3 0.0364(5) 0.0198(4) 0.0247(5) 0.0008(4) 0.0028(4) -0.0050(4) C4 0.0316(5) 0.0179(4) 0.0215(4) -0.0032(3) 0.0019(3) -0.0032(3) C5 0.0205(4) 0.0190(4) 0.0150(4) 0.0006(3) 0.0009(3) -0.0005(3) C6 0.0250(4) 0.0214(4) 0.0218(4) -0.0023(3) 0.0027(3) 0.0025(3) C7 0.0234(4) 0.0308(5) 0.0222(5) -0.0029(3) 0.0057(3) 0.0027(4) C8 0.0238(7) 0.0800(14) 0.0345(8) 0.0000 -0.0020(6) 0.0000 C9 0.0367(6) 0.0503(8) 0.0601(8) 0.0215(6) -0.0159(6) 0.0046(6) P1 0.02200(18) 0.02122(18) 0.01318(18) 0.0000 -0.00139(11) 0.0000 N1 0.0306(4) 0.0216(4) 0.0200(4) 0.0035(3) 0.0002(3) -0.0026(3) N2 0.0248(4) 0.0165(4) 0.0151(4) -0.0005(3) 0.0016(3) -0.0012(3) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C9 3_555 1.5274(15) yes C1 . C8 . 1.511(2) yes C1 . C9 . 1.5274(15) yes C1 . P1 . 1.8696(15) yes C2 . P1 . 1.8055(9) yes C2 . N1 . 1.3215(12) yes C2 . N2 . 1.3838(11) yes C3 . C4 . 1.3555(14) yes C3 . N1 . 1.3707(13) yes C3 . H31 . 0.952 no C4 . N2 . 1.3786(12) yes C4 . H41 . 0.944 no C5 . C5 3_555 1.3941(16) yes C5 . C6 . 1.3931(12) yes C5 . N2 . 1.4192(11) yes C6 . C7 . 1.3798(13) yes C6 . H61 . 0.933 no C7 . C7 3_555 1.382(2) yes C7 . H71 . 0.950 no C8 . H81 3_555 0.930 no C8 . H81 . 0.930 no C8 . H82 . 0.930 no C9 . H92 . 0.984 no C9 . H93 . 0.977 no C9 . H91 . 0.968 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 C9 3_555 C1 . C8 . 110.01(10) yes C9 3_555 C1 . C9 . 108.87(16) yes C8 . C1 . C9 . 110.01(10) yes C9 3_555 C1 . P1 . 104.71(8) yes C8 . C1 . P1 . 118.08(11) yes C9 . C1 . P1 . 104.71(8) yes P1 . C2 . N1 . 119.20(7) yes P1 . C2 . N2 . 130.16(7) yes N1 . C2 . N2 . 110.30(8) yes C4 . C3 . N1 . 110.77(9) yes C4 . C3 . H31 . 126.9 no N1 . C3 . H31 . 122.3 no C3 . C4 . N2 . 105.93(8) yes C3 . C4 . H41 . 130.5 no N2 . C4 . H41 . 123.5 no C5 3_555 C5 . C6 . 119.12(5) yes C5 3_555 C5 . N2 . 123.71(5) yes C6 . C5 . N2 . 117.17(8) yes C5 . C6 . C7 . 121.15(9) yes C5 . C6 . H61 . 119.8 no C7 . C6 . H61 . 119.0 no C7 3_555 C7 . C6 . 119.72(6) yes C7 3_555 C7 . H71 . 119.7 no C6 . C7 . H71 . 120.6 no C1 . C8 . H81 3_555 109.5 no C1 . C8 . H81 . 109.5 no H81 3_555 C8 . H81 . 109.4 no C1 . C8 . H82 . 109.5 no H81 3_555 C8 . H82 . 109.5 no H81 . C8 . H82 . 109.5 no C1 . C9 . H92 . 108.9 no C1 . C9 . H93 . 110.8 no H92 . C9 . H93 . 107.0 no C1 . C9 . H91 . 108.2 no H92 . C9 . H91 . 111.2 no H93 . C9 . H91 . 110.7 no C1 . P1 . C2 3_555 107.11(4) yes C1 . P1 . C2 . 107.11(4) yes C2 3_555 P1 . C2 . 99.43(6) yes C3 . N1 . C2 . 106.13(8) yes C5 . N2 . C2 . 129.69(8) yes C5 . N2 . C4 . 122.52(8) yes C2 . N2 . C4 . 106.87(7) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C4 . H41 . N1 5_665 169.19(3) 0.944 2.398 3.3295(15) yes _iucr_refine_instruction_details_constraints ; # # Punched on 13/12/11 at 15:54:49 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) H ( 82,X'S) RIDE C ( 9,X'S) H ( 92,X'S) H ( 93,X'S) H ( 91,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 13/12/11 at 15:54:49 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _database_code_depnum_ccdc_archive 'CCDC 932386' ####################################################################### # # 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_4 #TrackingRef 'cifcarine010212Bruker.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 10.2649(3) _cell_length_b 12.1611(4) _cell_length_c 12.7816(4) _cell_angle_alpha 81.178(2) _cell_angle_beta 71.935(2) _cell_angle_gamma 72.878(2) _cell_volume 1446.29(8) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' 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' 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' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C22 H26 F6 N5 O7 P1 S2 # Dc = 1.56 Fooo = 700.00 Mu = 3.29 M = 681.57 # Found Formula = C22 H26 F6 N5 O7 P1 S2 # Dc = 1.56 FOOO = 700.00 Mu = 3.29 M = 681.57 _chemical_formula_sum 'C22 H26 F6 N5 O7 P1 S2' _chemical_formula_moiety 'C18 H23 N4 O P, 2(C F3 O3 S), C2 H3 N' _chemical_compound_source ? _chemical_formula_weight 681.57 _cell_measurement_reflns_used 6698 _cell_measurement_theta_min 3 _cell_measurement_theta_max 28 _cell_measurement_temperature 120 _exptl_crystal_description planar _exptl_crystal_colour colorless _exptl_crystal_size_min 0.050 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 700 _exptl_absorpt_coefficient_mu 0.329 # Sheldrick geometric approximatio 0.95 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Siemens, 1996)' _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device_type 'Bruker Kappa Apex2' _diffrn_measurement_device Area _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 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _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 120 _diffrn_reflns_number 26900 _reflns_number_total 7263 _diffrn_reflns_av_R_equivalents 0.038 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 7263 # Theoretical number of reflections is about 16795 _diffrn_reflns_theta_min 1.756 _diffrn_reflns_theta_max 29.984 _diffrn_measured_fraction_theta_max 0.862 _diffrn_reflns_theta_full 25.186 _diffrn_measured_fraction_theta_full 0.920 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -13 _reflns_limit_h_max 14 _reflns_limit_k_min -16 _reflns_limit_k_max 17 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _atom_sites_solution_primary Direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.38 _refine_diff_density_max 0.34 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>3.0\s(I) _refine_ls_number_reflns 4746 _refine_ls_number_restraints 0 _refine_ls_number_parameters 388 _oxford_refine_ls_R_factor_ref 0.0365 _refine_ls_wR_factor_ref 0.0379 _refine_ls_goodness_of_fit_ref 1.1243 _refine_ls_shift/su_max 0.0003063 _refine_ls_shift/su_mean 0.0000317 # The values computed from all data _oxford_reflns_number_all 7240 _refine_ls_R_factor_all 0.0689 _refine_ls_wR_factor_all 0.0612 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5271 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_gt 0.0408 # 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: 0.775 -0.357E-01 0.334 ; # 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 C1 C 0.7627(2) 0.87597(17) 0.30463(18) 0.0180 1.0000 Uani . . . . . . C2 C 0.72422(19) 0.73258(16) 0.14984(17) 0.0155 1.0000 Uani . . . . . . C3 C 0.6001(2) 0.6623(2) 0.07565(19) 0.0234 1.0000 Uani . . . . . . C4 C 0.6584(2) 0.57683(18) 0.14093(18) 0.0204 1.0000 Uani . . . . . . C5 C 0.7974(2) 0.56037(16) 0.27252(17) 0.0160 1.0000 Uani . . . . . . C6 C 0.7113(2) 0.50898(17) 0.36108(18) 0.0208 1.0000 Uani . . . . . . C7 C 0.7675(2) 0.44343(18) 0.44314(19) 0.0240 1.0000 Uani . . . . . . C8 C 0.9090(2) 0.42944(18) 0.4368(2) 0.0249 1.0000 Uani . . . . . . C9 C 0.9938(2) 0.48391(17) 0.35080(19) 0.0206 1.0000 Uani . . . . . . C10 C 0.9377(2) 0.55009(16) 0.26846(17) 0.0160 1.0000 Uani . . . . . . C11 C 1.1688(2) 0.55306(17) 0.13396(19) 0.0205 1.0000 Uani . . . . . . C12 C 1.2253(2) 0.63376(18) 0.06578(19) 0.0211 1.0000 Uani . . . . . . C13 C 1.00036(19) 0.71866(16) 0.14455(17) 0.0151 1.0000 Uani . . . . . . C14 C 0.8073(2) 0.78771(18) 0.39454(19) 0.0238 1.0000 Uani . . . . . . C15 C 0.8269(2) 0.97882(19) 0.2927(2) 0.0274 1.0000 Uani . . . . . . C16 C 0.6001(2) 0.91754(19) 0.3307(2) 0.0250 1.0000 Uani . . . . . . C17 C 0.5908(2) 0.8717(2) 0.0261(2) 0.0268 1.0000 Uani . . . . . . C18 C 1.1446(2) 0.84396(18) 0.0114(2) 0.0251 1.0000 Uani . . . . . . C19 C 0.5216(2) 1.28664(19) 0.3280(2) 0.0267 1.0000 Uani . . . . . . C20 C 0.1984(2) 0.88201(19) 0.4067(2) 0.0253 1.0000 Uani . . . . . . C21 C 0.9298(3) 0.8209(3) -0.2354(3) 0.0464 1.0000 Uani . . . . . . C22 C 0.9528(3) 0.7314(2) -0.1488(2) 0.0335 1.0000 Uani . . . . . . N1 N 0.64157(17) 0.75823(15) 0.08181(15) 0.0186 1.0000 Uani . . . . . . N2 N 0.73533(16) 0.62101(14) 0.18719(14) 0.0162 1.0000 Uani . . . . . . N3 N 1.02855(16) 0.60602(13) 0.18217(14) 0.0156 1.0000 Uani . . . . . . N4 N 1.12043(17) 0.73540(14) 0.07304(15) 0.0176 1.0000 Uani . . . . . . N5 N 0.9687(3) 0.6619(2) -0.0795(2) 0.0464 1.0000 Uani . . . . . . O1 O 0.83190(15) 0.91651(12) 0.07674(13) 0.0222 1.0000 Uani . . . . . . O2 O 0.30464(16) 1.30475(14) 0.25830(16) 0.0349 1.0000 Uani . . . . . . O3 O 0.53246(18) 1.17837(14) 0.16670(15) 0.0306 1.0000 Uani . . . . . . O4 O 0.49393(16) 1.38627(14) 0.14048(14) 0.0270 1.0000 Uani . . . . . . O5 O 0.41154(16) 0.71594(14) 0.32475(15) 0.0300 1.0000 Uani . . . . . . O6 O 0.2948(2) 0.85044(17) 0.19902(16) 0.0414 1.0000 Uani . . . . . . O7 O 0.17708(17) 0.71297(15) 0.32033(14) 0.0315 1.0000 Uani . . . . . . P1 P 0.82754(5) 0.82448(4) 0.16676(4) 0.0149 1.0000 Uani . . . . . . S1 S 0.45531(5) 1.28872(4) 0.21069(5) 0.0194 1.0000 Uani . . . . . . S2 S 0.28034(5) 0.77848(5) 0.29991(5) 0.0221 1.0000 Uani . . . . . . F1 F 0.45658(18) 1.38207(13) 0.38213(13) 0.0427 1.0000 Uani . . . . . . F2 F 0.50334(18) 1.19678(13) 0.39910(13) 0.0411 1.0000 Uani . . . . . . F3 F 0.66046(15) 1.28049(13) 0.29420(14) 0.0373 1.0000 Uani . . . . . . F4 F 0.07028(16) 0.94385(16) 0.40047(16) 0.0523 1.0000 Uani . . . . . . F5 F 0.18421(19) 0.83020(14) 0.50711(13) 0.0448 1.0000 Uani . . . . . . F6 F 0.27397(17) 0.95695(13) 0.39727(16) 0.0482 1.0000 Uani . . . . . . H31 H 0.5405 0.6600 0.0326 0.0301 1.0000 Uiso R . . . . . H41 H 0.6488 0.5003 0.1550 0.0266 1.0000 Uiso R . . . . . H61 H 0.6150 0.5191 0.3650 0.0268 1.0000 Uiso R . . . . . H71 H 0.7087 0.4086 0.5026 0.0290 1.0000 Uiso R . . . . . H81 H 0.9477 0.3824 0.4926 0.0312 1.0000 Uiso R . . . . . H91 H 1.0896 0.4765 0.3480 0.0252 1.0000 Uiso R . . . . . H111 H 1.2120 0.4745 0.1483 0.0263 1.0000 Uiso R . . . . . H121 H 1.3195 0.6250 0.0202 0.0259 1.0000 Uiso R . . . . . H141 H 0.7630 0.7246 0.4053 0.0368 1.0000 Uiso R . . . . . H142 H 0.7766 0.8251 0.4639 0.0364 1.0000 Uiso R . . . . . H143 H 0.9106 0.7581 0.3742 0.0370 1.0000 Uiso R . . . . . H151 H 0.7927 1.0383 0.2393 0.0418 1.0000 Uiso R . . . . . H152 H 0.7973 1.0097 0.3636 0.0420 1.0000 Uiso R . . . . . H153 H 0.9309 0.9524 0.2682 0.0415 1.0000 Uiso R . . . . . H162 H 0.5747 0.9740 0.2720 0.0386 1.0000 Uiso R . . . . . H161 H 0.5653 0.9539 0.4000 0.0385 1.0000 Uiso R . . . . . H163 H 0.5602 0.8530 0.3364 0.0385 1.0000 Uiso R . . . . . H172 H 0.5460 0.8619 -0.0247 0.0432 1.0000 Uiso R . . . . . H171 H 0.6704 0.9016 -0.0098 0.0433 1.0000 Uiso R . . . . . H173 H 0.5251 0.9220 0.0809 0.0441 1.0000 Uiso R . . . . . H182 H 1.0679 0.8816 -0.0225 0.0405 1.0000 Uiso R . . . . . H181 H 1.1478 0.8947 0.0624 0.0406 1.0000 Uiso R . . . . . H183 H 1.2342 0.8270 -0.0446 0.0406 1.0000 Uiso R . . . . . H212 H 1.0193 0.8182 -0.2912 0.0702 1.0000 Uiso R . . . . . H211 H 0.8942 0.8951 -0.2037 0.0702 1.0000 Uiso R . . . . . H213 H 0.8620 0.8090 -0.2677 0.0699 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 0.0185(9) 0.0164(9) 0.0188(11) -0.0033(7) -0.0040(7) -0.0041(7) C2 0.0139(8) 0.0187(9) 0.0133(10) 0.0008(7) -0.0024(7) -0.0057(7) C3 0.0192(9) 0.0359(12) 0.0192(12) -0.0060(9) -0.0042(8) -0.0123(8) C4 0.0195(9) 0.0258(10) 0.0186(12) -0.0061(8) -0.0029(8) -0.0103(8) C5 0.0186(9) 0.0135(8) 0.0150(11) -0.0014(7) -0.0035(7) -0.0039(7) C6 0.0189(9) 0.0191(9) 0.0224(12) 0.0000(8) -0.0002(8) -0.0088(7) C7 0.0284(11) 0.0191(10) 0.0214(12) 0.0027(8) -0.0020(8) -0.0089(8) C8 0.0306(11) 0.0176(9) 0.0231(13) 0.0032(8) -0.0089(9) -0.0021(8) C9 0.0184(9) 0.0186(9) 0.0223(12) -0.0010(8) -0.0057(8) -0.0014(7) C10 0.0168(8) 0.0149(8) 0.0143(11) 0.0005(7) -0.0016(7) -0.0047(7) C11 0.0165(9) 0.0179(9) 0.0241(12) -0.0032(8) -0.0031(8) -0.0018(7) C12 0.0141(9) 0.0254(10) 0.0238(12) -0.0056(8) -0.0043(8) -0.0046(7) C13 0.0143(8) 0.0168(9) 0.0152(10) -0.0006(7) -0.0039(7) -0.0060(7) C14 0.0273(11) 0.0228(10) 0.0204(12) -0.0033(8) -0.0081(8) -0.0031(8) C15 0.0304(11) 0.0260(11) 0.0291(14) -0.0071(9) -0.0054(9) -0.0127(9) C16 0.0189(9) 0.0262(11) 0.0272(13) -0.0065(9) -0.0035(8) -0.0029(8) C17 0.0249(10) 0.0321(12) 0.0243(13) 0.0083(9) -0.0141(9) -0.0062(9) C18 0.0246(10) 0.0241(10) 0.0261(13) 0.0061(9) -0.0026(9) -0.0146(8) C19 0.0329(12) 0.0228(10) 0.0224(13) -0.0025(9) -0.0041(9) -0.0077(9) C20 0.0188(10) 0.0285(11) 0.0264(13) -0.0041(9) -0.0060(8) -0.0025(8) C21 0.0548(18) 0.0508(17) 0.0410(19) 0.0049(13) -0.0089(13) -0.0337(14) C22 0.0348(13) 0.0411(14) 0.0291(16) -0.0096(11) -0.0032(10) -0.0192(11) N1 0.0160(8) 0.0254(9) 0.0153(10) -0.0005(7) -0.0052(6) -0.0062(6) N2 0.0149(7) 0.0182(8) 0.0165(9) -0.0016(6) -0.0028(6) -0.0073(6) N3 0.0151(7) 0.0162(7) 0.0146(9) 0.0000(6) -0.0037(6) -0.0038(6) N4 0.0164(7) 0.0201(8) 0.0175(10) -0.0011(6) -0.0038(6) -0.0076(6) N5 0.0571(16) 0.0484(14) 0.0401(16) -0.0087(12) -0.0137(12) -0.0207(12) O1 0.0237(7) 0.0173(7) 0.0245(9) 0.0051(6) -0.0076(6) -0.0060(5) O2 0.0144(7) 0.0306(9) 0.0532(13) 0.0070(8) -0.0047(7) -0.0066(6) O3 0.0318(8) 0.0285(8) 0.0324(10) -0.0118(7) -0.0094(7) -0.0040(7) O4 0.0258(8) 0.0305(8) 0.0245(10) 0.0064(6) -0.0058(6) -0.0126(6) O5 0.0211(7) 0.0334(9) 0.0335(11) -0.0082(7) -0.0065(7) -0.0023(6) O6 0.0481(11) 0.0501(11) 0.0208(11) 0.0091(8) -0.0063(8) -0.0143(9) O7 0.0279(8) 0.0445(10) 0.0263(10) -0.0098(7) -0.0037(7) -0.0159(7) P1 0.0145(2) 0.0137(2) 0.0167(3) 0.00068(18) -0.00466(18) -0.00452(17) S1 0.0149(2) 0.0210(2) 0.0213(3) 0.00041(19) -0.00444(18) -0.00506(18) S2 0.0192(2) 0.0301(3) 0.0158(3) -0.0015(2) -0.00230(18) -0.00734(19) F1 0.0559(10) 0.0354(8) 0.0339(9) -0.0176(7) -0.0030(7) -0.0105(7) F2 0.0629(10) 0.0368(8) 0.0241(9) 0.0082(6) -0.0148(7) -0.0163(7) F3 0.0289(7) 0.0445(8) 0.0465(10) -0.0049(7) -0.0201(7) -0.0106(6) F4 0.0284(8) 0.0626(11) 0.0594(12) -0.0266(9) -0.0193(8) 0.0163(7) F5 0.0685(11) 0.0423(9) 0.0190(9) -0.0062(6) -0.0069(7) -0.0113(8) F6 0.0422(9) 0.0361(8) 0.0682(13) -0.0171(8) -0.0063(8) -0.0158(7) _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 . C14 . 1.530(3) yes C1 . C15 . 1.545(3) yes C1 . C16 . 1.537(3) yes C1 . P1 . 1.818(2) yes C2 . N1 . 1.339(3) yes C2 . N2 . 1.351(2) yes C2 . P1 . 1.8260(19) yes C3 . C4 . 1.346(3) yes C3 . N1 . 1.374(3) yes C3 . H31 . 0.950 no C4 . N2 . 1.378(2) yes C4 . H41 . 0.949 no C5 . C6 . 1.393(3) yes C5 . C10 . 1.394(3) yes C5 . N2 . 1.431(3) yes C6 . C7 . 1.385(3) yes C6 . H61 . 0.945 no C7 . C8 . 1.390(3) yes C7 . H71 . 0.942 no C8 . C9 . 1.389(3) yes C8 . H81 . 0.954 no C9 . C10 . 1.389(3) yes C9 . H91 . 0.951 no C10 . N3 . 1.433(2) yes C11 . C12 . 1.349(3) yes C11 . N3 . 1.375(2) yes C11 . H111 . 0.943 no C12 . N4 . 1.373(3) yes C12 . H121 . 0.945 no C13 . N3 . 1.357(2) yes C13 . N4 . 1.337(2) yes C13 . P1 . 1.8274(19) yes C14 . H141 . 0.974 no C14 . H142 . 0.979 no C14 . H143 . 0.977 no C15 . H151 . 0.980 no C15 . H152 . 0.959 no C15 . H153 . 0.981 no C16 . H162 . 0.980 no C16 . H161 . 0.969 no C16 . H163 . 0.971 no C17 . N1 . 1.479(3) yes C17 . H172 . 0.942 no C17 . H171 . 0.949 no C17 . H173 . 0.957 no C18 . N4 . 1.476(3) yes C18 . H182 . 0.977 no C18 . H181 . 0.978 no C18 . H183 . 0.962 no C19 . S1 . 1.823(3) yes C19 . F1 . 1.332(3) yes C19 . F2 . 1.329(3) yes C19 . F3 . 1.338(3) yes C20 . S2 . 1.830(2) yes C20 . F4 . 1.329(2) yes C20 . F5 . 1.325(3) yes C20 . F6 . 1.331(3) yes C21 . C22 . 1.451(4) yes C21 . H212 . 0.969 no C21 . H211 . 0.969 no C21 . H213 . 0.965 no C22 . N5 . 1.142(4) yes O1 . P1 . 1.4768(15) yes O2 . S1 . 1.4406(15) yes O3 . S1 . 1.4401(16) yes O4 . S1 . 1.4490(16) yes O5 . S2 . 1.4425(17) yes O6 . S2 . 1.4362(19) yes O7 . S2 . 1.4451(17) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C14 . C1 . C15 . 109.71(18) yes C14 . C1 . C16 . 110.97(18) yes C15 . C1 . C16 . 110.61(17) yes C14 . C1 . P1 . 115.02(14) yes C15 . C1 . P1 . 103.76(14) yes C16 . C1 . P1 . 106.52(15) yes N1 . C2 . N2 . 107.31(16) yes N1 . C2 . P1 . 125.02(15) yes N2 . C2 . P1 . 126.76(15) yes C4 . C3 . N1 . 107.50(18) yes C4 . C3 . H31 . 128.2 no N1 . C3 . H31 . 124.3 no C3 . C4 . N2 . 107.19(18) yes C3 . C4 . H41 . 127.9 no N2 . C4 . H41 . 124.9 no C6 . C5 . C10 . 120.42(19) yes C6 . C5 . N2 . 116.83(17) yes C10 . C5 . N2 . 122.74(17) yes C5 . C6 . C7 . 119.60(19) yes C5 . C6 . H61 . 120.0 no C7 . C6 . H61 . 120.4 no C6 . C7 . C8 . 119.9(2) yes C6 . C7 . H71 . 119.1 no C8 . C7 . H71 . 121.0 no C7 . C8 . C9 . 120.6(2) yes C7 . C8 . H81 . 119.5 no C9 . C8 . H81 . 119.8 no C8 . C9 . C10 . 119.60(19) yes C8 . C9 . H91 . 120.6 no C10 . C9 . H91 . 119.8 no C5 . C10 . C9 . 119.71(18) yes C5 . C10 . N3 . 122.64(18) yes C9 . C10 . N3 . 117.65(17) yes C12 . C11 . N3 . 106.91(17) yes C12 . C11 . H111 . 129.3 no N3 . C11 . H111 . 123.8 no C11 . C12 . N4 . 107.72(17) yes C11 . C12 . H121 . 128.0 no N4 . C12 . H121 . 124.3 no N3 . C13 . N4 . 107.07(16) yes N3 . C13 . P1 . 127.74(14) yes N4 . C13 . P1 . 124.49(15) yes C1 . C14 . H141 . 110.2 no C1 . C14 . H142 . 109.3 no H141 . C14 . H142 . 108.7 no C1 . C14 . H143 . 109.9 no H141 . C14 . H143 . 110.2 no H142 . C14 . H143 . 108.4 no C1 . C15 . H151 . 110.0 no C1 . C15 . H152 . 108.0 no H151 . C15 . H152 . 109.7 no C1 . C15 . H153 . 109.8 no H151 . C15 . H153 . 109.8 no H152 . C15 . H153 . 109.6 no C1 . C16 . H162 . 109.2 no C1 . C16 . H161 . 107.2 no H162 . C16 . H161 . 109.7 no C1 . C16 . H163 . 110.4 no H162 . C16 . H163 . 109.8 no H161 . C16 . H163 . 110.5 no N1 . C17 . H172 . 108.8 no N1 . C17 . H171 . 108.1 no H172 . C17 . H171 . 111.4 no N1 . C17 . H173 . 108.3 no H172 . C17 . H173 . 110.5 no H171 . C17 . H173 . 109.7 no N4 . C18 . H182 . 110.0 no N4 . C18 . H181 . 108.8 no H182 . C18 . H181 . 109.8 no N4 . C18 . H183 . 109.0 no H182 . C18 . H183 . 110.0 no H181 . C18 . H183 . 109.2 no S1 . C19 . F1 . 111.51(17) yes S1 . C19 . F2 . 111.67(16) yes F1 . C19 . F2 . 108.0(2) yes S1 . C19 . F3 . 110.49(16) yes F1 . C19 . F3 . 107.15(19) yes F2 . C19 . F3 . 107.83(19) yes S2 . C20 . F4 . 111.14(16) yes S2 . C20 . F5 . 111.86(15) yes F4 . C20 . F5 . 107.77(19) yes S2 . C20 . F6 . 112.17(16) yes F4 . C20 . F6 . 106.46(19) yes F5 . C20 . F6 . 107.1(2) yes C22 . C21 . H212 . 109.0 no C22 . C21 . H211 . 108.7 no H212 . C21 . H211 . 109.4 no C22 . C21 . H213 . 109.9 no H212 . C21 . H213 . 109.9 no H211 . C21 . H213 . 110.0 no C21 . C22 . N5 . 178.9(3) yes C17 . N1 . C3 . 123.03(18) yes C17 . N1 . C2 . 127.64(17) yes C3 . N1 . C2 . 109.20(17) yes C5 . N2 . C4 . 123.48(17) yes C5 . N2 . C2 . 127.13(16) yes C4 . N2 . C2 . 108.80(17) yes C10 . N3 . C11 . 122.85(16) yes C10 . N3 . C13 . 127.66(16) yes C11 . N3 . C13 . 109.02(16) yes C18 . N4 . C12 . 123.00(17) yes C18 . N4 . C13 . 127.71(17) yes C12 . N4 . C13 . 109.27(16) yes C13 . P1 . C2 . 98.58(8) yes C13 . P1 . C1 . 112.18(9) yes C2 . P1 . C1 . 111.36(9) yes C13 . P1 . O1 . 110.05(9) yes C2 . P1 . O1 . 109.00(9) yes C1 . P1 . O1 . 114.50(9) yes C19 . S1 . O4 . 103.13(10) yes C19 . S1 . O2 . 104.16(11) yes O4 . S1 . O2 . 114.22(10) yes C19 . S1 . O3 . 103.26(10) yes O4 . S1 . O3 . 114.36(10) yes O2 . S1 . O3 . 115.55(10) yes C20 . S2 . O7 . 102.76(10) yes C20 . S2 . O5 . 102.70(10) yes O7 . S2 . O5 . 115.03(11) yes C20 . S2 . O6 . 103.46(12) yes O7 . S2 . O6 . 114.81(12) yes O5 . S2 . O6 . 115.50(11) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C3 . H31 . O4 2_675 151.16(6) 0.950 2.514 3.377(3) yes C4 . H41 . O4 1_545 140.31(6) 0.949 2.458 3.245(3) yes C11 . H111 . O2 1_645 155.99(7) 0.943 2.435 3.319(3) yes C12 . H121 . O4 2_775 158.73(7) 0.945 2.323 3.223(3) yes C14 . H143 . O7 1_655 171.45(6) 0.977 2.514 3.484(3) yes C17 . H172 . O3 2_675 171.50(7) 0.942 2.365 3.300(3) yes C17 . H171 . O1 . 123.87(7) 0.949 2.320 2.956(3) yes C18 . H182 . O1 . 122.32(7) 0.977 2.305 2.945(3) yes C18 . H181 . O6 1_655 128.83(7) 0.978 2.546 3.250(3) yes C18 . H183 . O3 2_775 166.13(7) 0.962 2.408 3.351(3) yes C21 . H213 . O2 2_675 146.13(9) 0.965 2.464 3.309(3) yes _iucr_refine_instruction_details_constraints ; # # Punched on 02/02/12 at 16:51:00 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 14,X'S) H ( 141,X'S) H ( 142,X'S) H ( 143,X'S) RIDE C ( 15,X'S) H ( 151,X'S) H ( 152,X'S) H ( 153,X'S) RIDE C ( 16,X'S) H ( 162,X'S) H ( 161,X'S) H ( 163,X'S) RIDE C ( 17,X'S) H ( 172,X'S) H ( 171,X'S) H ( 173,X'S) RIDE C ( 18,X'S) H ( 182,X'S) H ( 181,X'S) H ( 183,X'S) RIDE C ( 21,X'S) H ( 212,X'S) H ( 211,X'S) H ( 213,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 02/02/12 at 16:51:00 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details -2 -4 8 x . _database_code_depnum_ccdc_archive 'CCDC 932387'