# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2011
data_global
_journal_coden_Cambridge 222
loop_
_publ_author_name
'Housecroft, Catherine'
'Constable, Edwin'
'Kopecky, Peter'
'Zampese, Jennifer'
'Neuburger, Markus'
'Bozic-Weber, Biljana'
_publ_contact_author_name 'Housecroft, Catherine'
_publ_contact_author_email Catherine.Housecroft@unibas.ch
_publ_section_title
;
The intramolecular aryl embrace: from light emission to light absorption
;
# Attachment '- PKA176.CIF'
data_pka176
_database_code_depnum_ccdc_archive 'CCDC 828945'
#TrackingRef '- PKA176.CIF'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C32 H24 Cu N4, F6 P'
_chemical_formula_sum 'C32 H24 Cu F6 N4 P'
_chemical_formula_weight 673.07
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M C2/c
_symmetry_space_group_name_Hall -C2yc
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 8.0516(13)
_cell_length_b 27.170(6)
_cell_length_c 13.159(2)
_cell_angle_alpha 90.00
_cell_angle_beta 96.239(13)
_cell_angle_gamma 90.00
_cell_volume 2861.7(9)
_cell_formula_units_Z 4
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 14970
_cell_measurement_theta_min 5.30
_cell_measurement_theta_max 67.86
_exptl_crystal_description plate
_exptl_crystal_colour red
_exptl_crystal_size_max 0.40
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.02
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.562
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1368
_exptl_absorpt_coefficient_mu 0.889
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.7175
_exptl_absorpt_correction_T_max 0.9824
_exptl_absorpt_process_details '(Blessing 1951)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Stoe IPDS'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 22088
_diffrn_reflns_av_R_equivalents 0.0572
_diffrn_reflns_av_sigmaI/netI 0.0247
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -35
_diffrn_reflns_limit_k_max 35
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_theta_min 2.65
_diffrn_reflns_theta_max 27.99
_reflns_number_total 3452
_reflns_number_gt 3218
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Stoe IPDS'
_computing_cell_refinement 'Stoe IPDS'
_computing_data_reduction 'Stoe IPDS'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0499P)^2^+2.7485P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3452
_refine_ls_number_parameters 201
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0390
_refine_ls_R_factor_gt 0.0358
_refine_ls_wR_factor_ref 0.0967
_refine_ls_wR_factor_gt 0.0944
_refine_ls_goodness_of_fit_ref 1.073
_refine_ls_restrained_S_all 1.073
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.574472(11) 0.7500 0.02762(10) Uani 1 2 d S . .
N1 N 0.37470(19) 0.53665(5) 0.63285(10) 0.0286(3) Uani 1 1 d . . .
N2 N 0.56658(17) 0.61557(5) 0.62994(10) 0.0254(3) Uani 1 1 d . . .
C1 C 0.2880(2) 0.49482(7) 0.63797(14) 0.0341(4) Uani 1 1 d . . .
H1A H 0.2812 0.4805 0.7033 0.041 Uiso 1 1 calc R . .
C2 C 0.2077(2) 0.47132(7) 0.55307(15) 0.0378(4) Uani 1 1 d . . .
H2A H 0.1480 0.4416 0.5598 0.045 Uiso 1 1 calc R . .
C3 C 0.2169(3) 0.49235(8) 0.45847(15) 0.0387(4) Uani 1 1 d . . .
H3A H 0.1624 0.4774 0.3986 0.046 Uiso 1 1 calc R . .
C4 C 0.3060(2) 0.53530(7) 0.45169(13) 0.0338(4) Uani 1 1 d . . .
H4A H 0.3132 0.5503 0.3871 0.041 Uiso 1 1 calc R . .
C5 C 0.3851(2) 0.55649(6) 0.53989(12) 0.0271(3) Uani 1 1 d . . .
C6 C 0.4859(2) 0.60204(6) 0.53873(12) 0.0270(3) Uani 1 1 d . . .
C7 C 0.4970(3) 0.62909(7) 0.45035(14) 0.0369(4) Uani 1 1 d . . .
H7A H 0.4381 0.6191 0.3873 0.044 Uiso 1 1 calc R . .
C8 C 0.5955(3) 0.67084(8) 0.45570(15) 0.0411(4) Uani 1 1 d . . .
H8A H 0.6081 0.6894 0.3958 0.049 Uiso 1 1 calc R . .
C9 C 0.6749(3) 0.68530(8) 0.54860(15) 0.0382(4) Uani 1 1 d . . .
H9A H 0.7412 0.7143 0.5536 0.046 Uiso 1 1 calc R . .
C10 C 0.6578(2) 0.65732(7) 0.63518(13) 0.0300(3) Uani 1 1 d . . .
C11 C 0.7385(2) 0.67239(7) 0.73652(14) 0.0342(4) Uani 1 1 d . . .
C12 C 0.8210(2) 0.63839(9) 0.80274(14) 0.0391(4) Uani 1 1 d . . .
H12A H 0.8289 0.6051 0.7821 0.047 Uiso 1 1 calc R . .
C13 C 0.8921(3) 0.65285(11) 0.89911(16) 0.0543(6) Uani 1 1 d . . .
H13A H 0.9483 0.6294 0.9441 0.065 Uiso 1 1 calc R . .
C14 C 0.8813(3) 0.70097(13) 0.9294(2) 0.0662(8) Uani 1 1 d . . .
H14A H 0.9292 0.7107 0.9955 0.079 Uiso 1 1 calc R . .
C15 C 0.8011(4) 0.73522(12) 0.8639(2) 0.0660(8) Uani 1 1 d . . .
H15A H 0.7944 0.7685 0.8851 0.079 Uiso 1 1 calc R . .
C16 C 0.7301(3) 0.72135(9) 0.7672(2) 0.0484(5) Uani 1 1 d . . .
H16A H 0.6761 0.7451 0.7222 0.058 Uiso 1 1 calc R . .
P1 P 0.0000 0.37802(3) 0.7500 0.03799(17) Uani 1 2 d S . .
F10 F 0.0000 0.43710(7) 0.7500 0.0586(5) Uani 1 2 d S . .
F11 F 0.0000 0.32083(9) 0.7500 0.1002(10) Uani 1 2 d S . .
F12 F -0.0368(2) 0.37949(7) 0.62937(10) 0.0663(4) Uani 1 1 d . . .
F13 F 0.1963(2) 0.37999(7) 0.74018(12) 0.0679(5) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.03422(17) 0.03179(17) 0.01659(14) 0.000 0.00153(10) 0.000
N1 0.0337(7) 0.0301(7) 0.0214(6) -0.0008(5) 0.0009(5) 0.0003(6)
N2 0.0264(6) 0.0285(7) 0.0215(6) 0.0010(5) 0.0042(5) 0.0032(5)
C1 0.0399(9) 0.0349(9) 0.0270(8) -0.0004(7) 0.0012(7) -0.0035(7)
C2 0.0365(9) 0.0378(10) 0.0385(10) -0.0058(8) 0.0008(8) -0.0048(7)
C3 0.0388(10) 0.0452(10) 0.0305(9) -0.0092(7) -0.0040(7) 0.0015(8)
C4 0.0351(9) 0.0424(10) 0.0226(8) -0.0027(7) -0.0025(6) 0.0047(7)
C5 0.0285(8) 0.0319(8) 0.0204(7) -0.0011(6) 0.0001(6) 0.0060(6)
C6 0.0293(8) 0.0310(8) 0.0206(7) 0.0018(6) 0.0017(6) 0.0063(6)
C7 0.0426(10) 0.0432(10) 0.0240(8) 0.0079(7) -0.0006(7) 0.0037(8)
C8 0.0467(11) 0.0439(11) 0.0326(9) 0.0167(8) 0.0036(8) 0.0020(8)
C9 0.0388(10) 0.0377(9) 0.0382(10) 0.0113(8) 0.0044(8) -0.0020(8)
C10 0.0278(8) 0.0327(8) 0.0298(8) 0.0038(6) 0.0048(6) 0.0011(6)
C11 0.0292(8) 0.0429(10) 0.0315(9) -0.0038(7) 0.0075(7) -0.0093(7)
C12 0.0331(9) 0.0577(12) 0.0268(8) 0.0023(8) 0.0042(7) -0.0126(8)
C13 0.0368(11) 0.097(2) 0.0287(10) 0.0008(11) 0.0031(8) -0.0219(11)
C14 0.0465(13) 0.112(2) 0.0409(12) -0.0288(14) 0.0098(10) -0.0290(15)
C15 0.0534(14) 0.0782(18) 0.0696(18) -0.0403(15) 0.0210(13) -0.0267(14)
C16 0.0423(11) 0.0497(12) 0.0549(13) -0.0157(10) 0.0134(10) -0.0133(9)
P1 0.0454(4) 0.0395(4) 0.0268(3) 0.000 -0.0066(3) 0.000
F10 0.0755(14) 0.0435(10) 0.0585(12) 0.000 0.0156(11) 0.000
F11 0.151(3) 0.0340(11) 0.112(2) 0.000 -0.001(2) 0.000
F12 0.0789(11) 0.0878(11) 0.0290(6) -0.0096(7) -0.0089(7) -0.0051(8)
F13 0.0474(8) 0.0969(13) 0.0580(9) -0.0091(8) -0.0012(7) 0.0163(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 2.0278(14) . ?
Cu1 N1 2.0278(14) 2_656 ?
Cu1 N2 2.0530(14) . ?
Cu1 N2 2.0530(14) 2_656 ?
N1 C1 1.340(2) . ?
N1 C5 1.348(2) . ?
N2 C10 1.349(2) . ?
N2 C6 1.352(2) . ?
C1 C2 1.384(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.379(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.378(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.387(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.481(3) . ?
C6 C7 1.387(2) . ?
C7 C8 1.381(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.374(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.389(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.476(2) . ?
C11 C12 1.389(3) . ?
C11 C16 1.394(3) . ?
C12 C13 1.390(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.372(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.380(5) . ?
C14 H14A 0.9500 . ?
C15 C16 1.389(4) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
P1 F11 1.554(2) . ?
P1 F12 1.5834(14) . ?
P1 F12 1.5834(14) 2_556 ?
P1 F13 1.6003(17) . ?
P1 F13 1.6003(17) 2_556 ?
P1 F10 1.605(2) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N1 119.11(8) . 2_656 ?
N1 Cu1 N2 80.82(6) . . ?
N1 Cu1 N2 135.29(6) 2_656 . ?
N1 Cu1 N2 135.29(6) . 2_656 ?
N1 Cu1 N2 80.82(6) 2_656 2_656 ?
N2 Cu1 N2 114.09(8) . 2_656 ?
C1 N1 C5 117.97(15) . . ?
C1 N1 Cu1 127.64(12) . . ?
C5 N1 Cu1 114.37(12) . . ?
C10 N2 C6 118.72(14) . . ?
C10 N2 Cu1 127.18(11) . . ?
C6 N2 Cu1 113.25(11) . . ?
N1 C1 C2 123.43(17) . . ?
N1 C1 H1A 118.3 . . ?
C2 C1 H1A 118.3 . . ?
C3 C2 C1 118.12(18) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?
C4 C3 C2 119.26(17) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 119.50(17) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
N1 C5 C4 121.71(17) . . ?
N1 C5 C6 115.57(14) . . ?
C4 C5 C6 122.72(16) . . ?
N2 C6 C7 122.11(17) . . ?
N2 C6 C5 115.41(14) . . ?
C7 C6 C5 122.47(16) . . ?
C8 C7 C6 118.79(17) . . ?
C8 C7 H7A 120.6 . . ?
C6 C7 H7A 120.6 . . ?
C9 C8 C7 119.28(17) . . ?
C9 C8 H8A 120.4 . . ?
C7 C8 H8A 120.4 . . ?
C8 C9 C10 119.69(19) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
N2 C10 C9 121.35(17) . . ?
N2 C10 C11 117.59(15) . . ?
C9 C10 C11 121.06(17) . . ?
C12 C11 C16 119.2(2) . . ?
C12 C11 C10 121.07(18) . . ?
C16 C11 C10 119.72(19) . . ?
C11 C12 C13 120.4(2) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C15 120.1(2) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C15 C16 C11 119.7(3) . . ?
C15 C16 H16A 120.1 . . ?
C11 C16 H16A 120.1 . . ?
F11 P1 F12 91.44(7) . . ?
F11 P1 F12 91.44(7) . 2_556 ?
F12 P1 F12 177.11(14) . 2_556 ?
F11 P1 F13 91.92(7) . . ?
F12 P1 F13 89.84(9) . . ?
F12 P1 F13 90.06(9) 2_556 . ?
F11 P1 F13 91.92(7) . 2_556 ?
F12 P1 F13 90.06(9) . 2_556 ?
F12 P1 F13 89.84(9) 2_556 2_556 ?
F13 P1 F13 176.16(15) . 2_556 ?
F11 P1 F10 180.0 . . ?
F12 P1 F10 88.56(7) . . ?
F12 P1 F10 88.56(7) 2_556 . ?
F13 P1 F10 88.08(7) . . ?
F13 P1 F10 88.08(7) 2_556 . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 27.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.334
_refine_diff_density_min -0.345
_refine_diff_density_rms 0.055
# Attachment '- PKA177.CIF'
data_pka177
_database_code_depnum_ccdc_archive 'CCDC 828946'
#TrackingRef '- PKA177.CIF'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C22 H20 Cu N4, F6 P'
_chemical_formula_sum 'C22 H20 Cu F6 N4 P'
_chemical_formula_weight 548.94
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M P-1
_symmetry_space_group_name_Hall -P1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 7.7042(8)
_cell_length_b 10.2596(11)
_cell_length_c 15.3283(14)
_cell_angle_alpha 107.978(8)
_cell_angle_beta 97.393(8)
_cell_angle_gamma 100.067(8)
_cell_volume 1112.90(19)
_cell_formula_units_Z 2
_cell_measurement_temperature 173(2)
_cell_measurement_reflns_used 29063
_cell_measurement_theta_min 5.48
_cell_measurement_theta_max 69.37
_exptl_crystal_description block
_exptl_crystal_colour red
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.22
_exptl_crystal_size_min 0.20
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.638
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 556
_exptl_absorpt_coefficient_mu 1.122
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.7154
_exptl_absorpt_correction_T_max 0.8067
_exptl_absorpt_process_details '(Blessing 1951)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 173(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Stoe IPDS'
_diffrn_measurement_method '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 23465
_diffrn_reflns_av_R_equivalents 0.0547
_diffrn_reflns_av_sigmaI/netI 0.0279
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 2.74
_diffrn_reflns_theta_max 26.50
_reflns_number_total 4574
_reflns_number_gt 4378
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Stoe IPDS'
_computing_cell_refinement 'Stoe IPDS'
_computing_data_reduction 'Stoe IPDS'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0597P)^2^+0.8533P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 4574
_refine_ls_number_parameters 309
_refine_ls_number_restraints 6
_refine_ls_R_factor_all 0.0428
_refine_ls_R_factor_gt 0.0414
_refine_ls_wR_factor_ref 0.1130
_refine_ls_wR_factor_gt 0.1117
_refine_ls_goodness_of_fit_ref 1.049
_refine_ls_restrained_S_all 1.052
_refine_ls_shift/su_max 0.034
_refine_ls_shift/su_mean 0.000
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.95005(4) 0.87535(3) 0.737247(18) 0.03872(12) Uani 1 1 d . . .
N1 N 1.0745(2) 0.7804(2) 0.81834(12) 0.0319(4) Uani 1 1 d . . .
N2 N 1.0375(3) 1.0424(2) 0.85412(13) 0.0387(4) Uani 1 1 d . . .
N3 N 0.7275(3) 0.7879(2) 0.63872(14) 0.0395(4) Uani 1 1 d . . .
N4 N 1.0590(3) 0.8865(2) 0.62433(14) 0.0407(4) Uani 1 1 d . . .
C1 C 0.9758(4) 0.5497(3) 0.7041(2) 0.0556(7) Uani 1 1 d . . .
H1A H 0.8516 0.5194 0.7103 0.083 Uiso 1 1 calc R . .
H1B H 1.0274 0.4672 0.6828 0.083 Uiso 1 1 calc R . .
H1C H 0.9777 0.5987 0.6584 0.083 Uiso 1 1 calc R . .
C2 C 1.0832(3) 0.6461(3) 0.79599(16) 0.0379(5) Uani 1 1 d . . .
C3 C 1.1873(4) 0.5983(3) 0.85474(19) 0.0453(6) Uani 1 1 d . . .
H3A H 1.1920 0.5019 0.8371 0.054 Uiso 1 1 calc R . .
C4 C 1.2839(4) 0.6931(3) 0.93930(19) 0.0487(6) Uani 1 1 d . . .
H4A H 1.3566 0.6627 0.9806 0.058 Uiso 1 1 calc R . .
C5 C 1.2742(3) 0.8312(3) 0.96334(17) 0.0442(6) Uani 1 1 d . . .
H5A H 1.3390 0.8976 1.0217 0.053 Uiso 1 1 calc R . .
C6 C 1.1688(3) 0.8732(3) 0.90175(15) 0.0352(5) Uani 1 1 d . . .
C7 C 1.1485(3) 1.0194(3) 0.92069(16) 0.0369(5) Uani 1 1 d . . .
C8 C 1.2361(4) 1.1283(3) 1.00195(19) 0.0499(6) Uani 1 1 d . . .
H8A H 1.3136 1.1111 1.0485 0.060 Uiso 1 1 calc R . .
C9 C 1.2101(4) 1.2616(3) 1.0147(2) 0.0580(8) Uani 1 1 d . . .
H9A H 1.2701 1.3373 1.0700 0.070 Uiso 1 1 calc R . .
C10 C 1.0975(4) 1.2845(3) 0.9473(2) 0.0557(7) Uani 1 1 d . . .
H10A H 1.0774 1.3758 0.9552 0.067 Uiso 1 1 calc R . .
C11 C 1.0133(4) 1.1722(3) 0.8674(2) 0.0497(6) Uani 1 1 d . . .
H11A H 0.9355 1.1881 0.8203 0.060 Uiso 1 1 calc R . .
C12 C 0.5392(5) 0.7794(4) 0.7501(3) 0.0649(8) Uani 1 1 d . . .
H12A H 0.6003 0.7234 0.7800 0.097 Uiso 1 1 calc R . .
H12B H 0.4107 0.7580 0.7515 0.097 Uiso 1 1 calc R . .
H12C H 0.5906 0.8797 0.7840 0.097 Uiso 1 1 calc R . .
C13 C 0.5635(4) 0.7446(3) 0.6518(2) 0.0479(6) Uani 1 1 d . . .
C14 C 0.4213(4) 0.6724(3) 0.5749(3) 0.0586(8) Uani 1 1 d . . .
H14A H 0.3038 0.6402 0.5839 0.070 Uiso 1 1 calc R . .
C15 C 0.4565(4) 0.6497(3) 0.4872(2) 0.0584(8) Uani 1 1 d . . .
H15A H 0.3618 0.6010 0.4347 0.070 Uiso 1 1 calc R . .
C16 C 0.6229(4) 0.6950(3) 0.47303(19) 0.0521(7) Uani 1 1 d . . .
H16A H 0.6451 0.6793 0.4115 0.062 Uiso 1 1 calc R . .
C17 C 0.7597(4) 0.7643(2) 0.54977(16) 0.0427(5) Uani 1 1 d U . .
C18 C 0.9445(4) 0.8228(2) 0.54309(17) 0.0419(5) Uani 1 1 d U . .
C19 C 0.9991(5) 0.8182(3) 0.45819(19) 0.0523(7) Uani 1 1 d . . .
H19A H 0.9183 0.7708 0.4000 0.063 Uiso 1 1 calc R . .
C20 C 1.1720(5) 0.8842(3) 0.4617(2) 0.0584(8) Uani 1 1 d . . .
H20A H 1.2121 0.8811 0.4052 0.070 Uiso 1 1 calc R . .
C21 C 1.2881(5) 0.9548(3) 0.5457(2) 0.0577(7) Uani 1 1 d . . .
H21A H 1.4062 1.0040 0.5482 0.069 Uiso 1 1 calc R . .
C22 C 1.2289(4) 0.9523(3) 0.6262(2) 0.0478(6) Uani 1 1 d . . .
H22A H 1.3092 0.9979 0.6846 0.057 Uiso 1 1 calc R . .
P1 P 0.54406(9) 1.32862(7) 0.79633(4) 0.04192(17) Uani 1 1 d . . .
F10 F 0.5577(3) 1.4592(2) 0.75977(13) 0.0640(5) Uani 1 1 d . . .
F11 F 0.5945(3) 1.2391(2) 0.70228(12) 0.0698(5) Uani 1 1 d . . .
F12 F 0.3360(2) 1.27688(19) 0.74688(12) 0.0581(4) Uani 1 1 d . . .
F13 F 0.4913(2) 1.41816(19) 0.88930(11) 0.0569(4) Uani 1 1 d . . .
F14 F 0.7510(2) 1.3829(2) 0.84562(14) 0.0679(5) Uani 1 1 d . . .
F15 F 0.5294(3) 1.19781(18) 0.83138(12) 0.0625(5) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.04167(18) 0.04916(19) 0.02248(16) 0.01242(12) -0.00153(11) 0.00819(13)
N1 0.0273(8) 0.0408(10) 0.0254(8) 0.0123(7) 0.0008(7) 0.0035(7)
N2 0.0416(10) 0.0437(10) 0.0284(9) 0.0111(8) 0.0068(8) 0.0059(8)
N3 0.0411(11) 0.0432(10) 0.0308(10) 0.0110(8) -0.0027(8) 0.0114(8)
N4 0.0525(12) 0.0396(10) 0.0347(10) 0.0158(8) 0.0102(9) 0.0153(9)
C1 0.0646(18) 0.0442(14) 0.0462(15) 0.0086(12) -0.0022(13) 0.0046(13)
C2 0.0348(11) 0.0465(13) 0.0322(11) 0.0155(10) 0.0057(9) 0.0058(9)
C3 0.0452(13) 0.0539(14) 0.0464(14) 0.0262(12) 0.0128(11) 0.0162(11)
C4 0.0403(13) 0.0761(18) 0.0392(13) 0.0321(13) 0.0036(10) 0.0174(12)
C5 0.0350(12) 0.0657(16) 0.0289(11) 0.0176(11) -0.0022(9) 0.0068(11)
C6 0.0265(10) 0.0520(13) 0.0241(10) 0.0128(9) 0.0028(8) 0.0028(9)
C7 0.0286(10) 0.0463(12) 0.0295(11) 0.0093(9) 0.0062(8) -0.0011(9)
C8 0.0378(13) 0.0586(16) 0.0368(13) 0.0040(11) -0.0002(10) -0.0035(11)
C9 0.0512(16) 0.0485(15) 0.0529(17) -0.0030(12) 0.0116(13) -0.0075(12)
C10 0.0666(18) 0.0426(14) 0.0536(16) 0.0097(12) 0.0256(14) 0.0037(12)
C11 0.0634(17) 0.0463(14) 0.0424(14) 0.0161(11) 0.0174(12) 0.0133(12)
C12 0.0518(17) 0.085(2) 0.066(2) 0.0363(18) 0.0181(15) 0.0119(16)
C13 0.0443(14) 0.0468(14) 0.0517(15) 0.0188(12) 0.0012(11) 0.0097(11)
C14 0.0428(14) 0.0518(16) 0.077(2) 0.0230(15) -0.0016(14) 0.0088(12)
C15 0.0633(18) 0.0466(15) 0.0518(17) 0.0105(12) -0.0170(14) 0.0100(13)
C16 0.0666(18) 0.0450(14) 0.0349(13) 0.0087(11) -0.0096(12) 0.0110(12)
C17 0.0646(14) 0.0333(10) 0.0278(10) 0.0094(8) -0.0059(10) 0.0176(10)
C18 0.0615(14) 0.0348(11) 0.0338(11) 0.0123(9) 0.0102(10) 0.0201(10)
C19 0.077(2) 0.0485(14) 0.0369(13) 0.0140(11) 0.0133(13) 0.0275(14)
C20 0.078(2) 0.0614(17) 0.0543(17) 0.0252(14) 0.0347(16) 0.0365(16)
C21 0.0608(18) 0.0589(17) 0.0671(19) 0.0296(15) 0.0277(15) 0.0222(14)
C22 0.0525(15) 0.0425(13) 0.0556(16) 0.0216(12) 0.0187(12) 0.0144(11)
P1 0.0456(4) 0.0489(4) 0.0275(3) 0.0110(3) 0.0004(2) 0.0097(3)
F10 0.0768(12) 0.0648(11) 0.0553(10) 0.0323(9) 0.0068(9) 0.0115(9)
F11 0.0820(13) 0.0871(13) 0.0401(9) 0.0104(9) 0.0196(9) 0.0337(11)
F12 0.0493(9) 0.0672(10) 0.0446(9) 0.0100(8) -0.0067(7) 0.0074(8)
F13 0.0700(11) 0.0618(10) 0.0315(8) 0.0065(7) 0.0047(7) 0.0166(8)
F14 0.0468(9) 0.0765(12) 0.0684(12) 0.0184(10) -0.0081(8) 0.0093(8)
F15 0.0842(13) 0.0534(9) 0.0478(9) 0.0215(8) -0.0014(9) 0.0127(9)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N3 1.996(2) . ?
Cu1 N2 1.998(2) . ?
Cu1 N4 2.044(2) . ?
Cu1 N1 2.0443(18) . ?
N1 C2 1.329(3) . ?
N1 C6 1.355(3) . ?
N2 C11 1.334(3) . ?
N2 C7 1.350(3) . ?
N3 C13 1.326(4) . ?
N3 C17 1.372(3) . ?
N4 C18 1.331(3) . ?
N4 C22 1.356(4) . ?
C1 C2 1.484(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.385(3) . ?
C3 C4 1.378(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.368(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.382(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.477(4) . ?
C7 C8 1.385(3) . ?
C8 C9 1.375(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.365(5) . ?
C9 H9A 0.9500 . ?
C10 C11 1.382(4) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 C13 1.483(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.409(4) . ?
C14 C15 1.363(5) . ?
C14 H14A 0.9500 . ?
C15 C16 1.354(5) . ?
C15 H15A 0.9500 . ?
C16 C17 1.379(4) . ?
C16 H16A 0.9500 . ?
C17 C18 1.474(4) . ?
C18 C19 1.408(4) . ?
C19 C20 1.371(5) . ?
C19 H19A 0.9500 . ?
C20 C21 1.373(5) . ?
C20 H20A 0.9500 . ?
C21 C22 1.374(4) . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9500 . ?
P1 F15 1.5844(18) . ?
P1 F13 1.5846(17) . ?
P1 F11 1.5889(18) . ?
P1 F14 1.5949(19) . ?
P1 F10 1.5970(18) . ?
P1 F12 1.6021(18) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N2 137.88(9) . . ?
N3 Cu1 N4 81.64(9) . . ?
N2 Cu1 N4 116.07(9) . . ?
N3 Cu1 N1 126.69(8) . . ?
N2 Cu1 N1 81.78(8) . . ?
N4 Cu1 N1 115.82(8) . . ?
C2 N1 C6 118.9(2) . . ?
C2 N1 Cu1 128.19(15) . . ?
C6 N1 Cu1 112.69(15) . . ?
C11 N2 C7 119.1(2) . . ?
C11 N2 Cu1 126.96(19) . . ?
C7 N2 Cu1 113.53(16) . . ?
C13 N3 C17 120.1(2) . . ?
C13 N3 Cu1 126.59(18) . . ?
C17 N3 Cu1 113.10(17) . . ?
C18 N4 C22 119.9(2) . . ?
C18 N4 Cu1 113.52(18) . . ?
C22 N4 Cu1 126.55(18) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 122.1(2) . . ?
N1 C2 C1 116.3(2) . . ?
C3 C2 C1 121.6(2) . . ?
C4 C3 C2 118.8(3) . . ?
C4 C3 H3A 120.6 . . ?
C2 C3 H3A 120.6 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
C4 C5 C6 119.2(2) . . ?
C4 C5 H5A 120.4 . . ?
C6 C5 H5A 120.4 . . ?
N1 C6 C5 121.5(2) . . ?
N1 C6 C7 114.9(2) . . ?
C5 C6 C7 123.7(2) . . ?
N2 C7 C8 120.8(2) . . ?
N2 C7 C6 116.3(2) . . ?
C8 C7 C6 122.8(2) . . ?
C9 C8 C7 119.5(3) . . ?
C9 C8 H8A 120.3 . . ?
C7 C8 H8A 120.3 . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9A 120.2 . . ?
C8 C9 H9A 120.2 . . ?
C9 C10 C11 118.7(3) . . ?
C9 C10 H10A 120.6 . . ?
C11 C10 H10A 120.6 . . ?
N2 C11 C10 122.3(3) . . ?
N2 C11 H11A 118.8 . . ?
C10 C11 H11A 118.8 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 120.5(3) . . ?
N3 C13 C12 116.6(2) . . ?
C14 C13 C12 122.9(3) . . ?
C15 C14 C13 118.3(3) . . ?
C15 C14 H14A 120.8 . . ?
C13 C14 H14A 120.8 . . ?
C16 C15 C14 121.6(3) . . ?
C16 C15 H15A 119.2 . . ?
C14 C15 H15A 119.2 . . ?
C15 C16 C17 118.7(3) . . ?
C15 C16 H16A 120.7 . . ?
C17 C16 H16A 120.7 . . ?
N3 C17 C16 120.7(3) . . ?
N3 C17 C18 115.8(2) . . ?
C16 C17 C18 123.5(3) . . ?
N4 C18 C19 120.8(3) . . ?
N4 C18 C17 115.3(2) . . ?
C19 C18 C17 123.8(2) . . ?
C20 C19 C18 118.2(3) . . ?
C20 C19 H19A 120.9 . . ?
C18 C19 H19A 120.9 . . ?
C19 C20 C21 121.0(3) . . ?
C19 C20 H20A 119.5 . . ?
C21 C20 H20A 119.5 . . ?
C20 C21 C22 118.2(3) . . ?
C20 C21 H21A 120.9 . . ?
C22 C21 H21A 120.9 . . ?
N4 C22 C21 121.8(3) . . ?
N4 C22 H22A 119.1 . . ?
C21 C22 H22A 119.1 . . ?
F15 P1 F13 90.27(10) . . ?
F15 P1 F11 90.14(11) . . ?
F13 P1 F11 179.19(11) . . ?
F15 P1 F14 90.34(11) . . ?
F13 P1 F14 89.73(11) . . ?
F11 P1 F14 90.96(12) . . ?
F15 P1 F10 179.31(11) . . ?
F13 P1 F10 90.25(10) . . ?
F11 P1 F10 89.34(11) . . ?
F14 P1 F10 90.11(11) . . ?
F15 P1 F12 90.60(11) . . ?
F13 P1 F12 89.87(10) . . ?
F11 P1 F12 89.43(11) . . ?
F14 P1 F12 178.98(11) . . ?
F10 P1 F12 88.95(11) . . ?
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full 26.50
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max 0.608
_refine_diff_density_min -0.502
_refine_diff_density_rms 0.062
# Attachment '- ml7.cif'
data_ml7_123k
_database_code_depnum_ccdc_archive 'CCDC 828947'
#TrackingRef '- ml7.cif'
_audit_creation_date 09-05-06
_audit_creation_method CRYSTALS_ver_12.86
_oxford_structure_analysis_title 'ml7_123k_0m in P2/c'
_chemical_name_systematic ?
_chemical_melting_point ?
_cell_length_a 11.6298(5)
_cell_length_b 8.6881(3)
_cell_length_c 13.7113(6)
_cell_angle_alpha 90
_cell_angle_beta 107.915(2)
_cell_angle_gamma 90
_cell_volume 1318.23(9)
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P 2/c '
_symmetry_space_group_name_Hall '-P 2yc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y,-z+1/2
x,-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 0.0033 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'
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'
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'
Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 2
# Given Formula = C28 H20 Cu1 F6 N4 O2 P1
# Dc = 1.65 Fooo = 660.00 Mu = 9.67 M = 326.50
# Found Formula = C28 H20 Cu1 F6 N4 O2 P1
# Dc = 1.65 FOOO = 660.00 Mu = 9.67 M = 326.50
_chemical_formula_sum 'C28 H20 Cu1 F6 N4 O2 P1'
_chemical_formula_moiety 'C28 H20 Cu N4 O2, F6 P'
_chemical_compound_source ?
_chemical_formula_weight 653.00
_cell_measurement_reflns_used 9331
_cell_measurement_theta_min 4
_cell_measurement_theta_max 41
_cell_measurement_temperature 123
_exptl_crystal_description plate
_exptl_crystal_colour red
_exptl_crystal_size_min 0.02
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_max 0.21
_exptl_crystal_density_diffrn 1.645
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 660
_exptl_absorpt_coefficient_mu 0.967
# Sheldrick geometric approximatio 0.89 0.98
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min 0.89
_exptl_absorpt_correction_T_max 0.98
_diffrn_measurement_device 'Bruker Kappa Apex2'
_diffrn_measurement_device_type 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 123
_diffrn_reflns_number 61626
_reflns_number_total 9825
_diffrn_reflns_av_R_equivalents 0.036
# Number of reflections with Friedels Law is 9825
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 9816
_diffrn_reflns_theta_min 2.344
_diffrn_reflns_theta_max 43.106
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 43.106
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min -22
_diffrn_reflns_limit_h_max 22
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -26
_diffrn_reflns_limit_l_max 26
_reflns_limit_h_min -22
_reflns_limit_h_max 21
_reflns_limit_k_min 0
_reflns_limit_k_max 16
_reflns_limit_l_min 0
_reflns_limit_l_max 26
_oxford_diffrn_Wilson_B_factor 1.35
_oxford_diffrn_Wilson_scale 79.49
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.48
_refine_diff_density_max 0.65
# 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 8405
_refine_ls_number_restraints 0
_refine_ls_number_parameters 191
_oxford_refine_ls_R_factor_ref 0.0364
_refine_ls_wR_factor_ref 0.0336
_refine_ls_goodness_of_fit_ref 0.9996
_refine_ls_shift/su_max 0.000670
# The values computed from all data
_oxford_reflns_number_all 9814
_refine_ls_R_factor_all 0.0470
_refine_ls_wR_factor_all 0.0613
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 8892
_refine_ls_R_factor_gt 0.0394
_refine_ls_wR_factor_gt 0.0354
# 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:
0.809E-01 0.336E-01 -0.253E-01 -0.301E-01
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.
Watkin D.J. (1994).
Acta Cryst, A50, 411-437.
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
Bruker Analytical X-ray Systems, Inc., 2006. Apex2,
Version 2 User Manual, M86-E01078, Madison, WI.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.5000 0.392746(14) 0.7500 0.0169 1.0000 Uani S T . . . . .
N1 N 0.36251(6) 0.28536(7) 0.64755(5) 0.0178 1.0000 Uani . . . . . . .
N2 N 0.47558(5) 0.54395(6) 0.62642(4) 0.0138 1.0000 Uani . . . . . . .
C1 C 0.32206(8) 0.14149(9) 0.65184(7) 0.0244 1.0000 Uani . . . . . . .
C2 C 0.22522(9) 0.07965(11) 0.57519(7) 0.0300 1.0000 Uani . . . . . . .
C3 C 0.16482(9) 0.17147(13) 0.49314(7) 0.0317 1.0000 Uani . . . . . . .
C4 C 0.20597(7) 0.32027(11) 0.48744(6) 0.0253 1.0000 Uani . . . . . . .
C5 C 0.30733(6) 0.37227(8) 0.56447(5) 0.0170 1.0000 Uani . . . . . . .
C6 C 0.36398(6) 0.52340(7) 0.55913(5) 0.0159 1.0000 Uani . . . . . . .
C7 C 0.30676(7) 0.63526(9) 0.48765(6) 0.0225 1.0000 Uani . . . . . . .
C8 C 0.36735(8) 0.77161(10) 0.48408(7) 0.0271 1.0000 Uani . . . . . . .
C9 C 0.48272(7) 0.79260(9) 0.55112(6) 0.0240 1.0000 Uani . . . . . . .
C10 C 0.53429(6) 0.67625(7) 0.62147(5) 0.0155 1.0000 Uani . . . . . . .
C11 C 0.65761(6) 0.69205(7) 0.68916(5) 0.0156 1.0000 Uani . . . . . . .
C12 C 0.74247(6) 0.59024(8) 0.74347(5) 0.0179 1.0000 Uani . . . . . . .
C13 C 0.85136(7) 0.67602(9) 0.78589(6) 0.0224 1.0000 Uani . . . . . . .
C14 C 0.82558(7) 0.82331(9) 0.75455(6) 0.0240 1.0000 Uani . . . . . . .
O1 O 0.70739(5) 0.83679(6) 0.69547(5) 0.0207 1.0000 Uani . . . . . . .
P2 P 1.0000 0.24205(3) 0.7500 0.0182 1.0000 Uani S T . . . . .
F1 F 0.97945(6) 0.11105(7) 0.66359(5) 0.0320 1.0000 Uani . . . . . . .
F2 F 0.97947(6) 0.37206(7) 0.66357(5) 0.0333 1.0000 Uani . . . . . . .
F3 F 0.85787(5) 0.24110(7) 0.73551(5) 0.0300 1.0000 Uani . . . . . . .
H11 H 0.3614 0.0830 0.7097 0.0304 1.0000 Uiso R . . . . . .
H121 H 0.7302 0.4867 0.7481 0.0233 1.0000 Uiso R . . . . . .
H71 H 0.2289 0.6200 0.4437 0.0266 1.0000 Uiso R . . . . . .
H41 H 0.1671 0.3829 0.4305 0.0306 1.0000 Uiso R . . . . . .
H31 H 0.0978 0.1325 0.4407 0.0393 1.0000 Uiso R . . . . . .
H91 H 0.5249 0.8813 0.5519 0.0293 1.0000 Uiso R . . . . . .
H141 H 0.8731 0.9101 0.7661 0.0291 1.0000 Uiso R . . . . . .
H81 H 0.3327 0.8491 0.4384 0.0309 1.0000 Uiso R . . . . . .
H131 H 0.9263 0.6403 0.8265 0.0279 1.0000 Uiso R . . . . . .
H21 H 0.2009 -0.0207 0.5812 0.0386 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
Cu1 0.01781(5) 0.01564(4) 0.01518(4) 0.0000 0.00181(3) 0.0000
N1 0.0198(2) 0.01512(19) 0.0189(2) -0.00241(16) 0.00668(17) -0.00299(16)
N2 0.01383(17) 0.01385(17) 0.01317(16) -0.00076(14) 0.00350(14) -0.00038(14)
C1 0.0304(3) 0.0176(2) 0.0274(3) -0.0036(2) 0.0119(3) -0.0075(2)
C2 0.0377(4) 0.0261(3) 0.0300(3) -0.0103(3) 0.0161(3) -0.0178(3)
C3 0.0323(4) 0.0403(4) 0.0236(3) -0.0112(3) 0.0100(3) -0.0218(4)
C4 0.0219(3) 0.0352(4) 0.0175(2) -0.0046(2) 0.0041(2) -0.0121(3)
C5 0.0161(2) 0.0202(2) 0.0150(2) -0.00394(17) 0.00525(17) -0.00397(18)
C6 0.0148(2) 0.0176(2) 0.0143(2) -0.00111(17) 0.00311(16) -0.00030(17)
C7 0.0192(3) 0.0235(3) 0.0202(3) 0.0026(2) -0.0008(2) 0.0023(2)
C8 0.0262(3) 0.0219(3) 0.0270(3) 0.0078(2) -0.0013(3) 0.0037(2)
C9 0.0249(3) 0.0163(2) 0.0266(3) 0.0064(2) 0.0016(2) 0.0000(2)
C10 0.0161(2) 0.01285(19) 0.0166(2) 0.00052(16) 0.00394(17) -0.00024(16)
C11 0.0163(2) 0.01250(19) 0.0176(2) -0.00095(16) 0.00483(17) -0.00196(16)
C12 0.0167(2) 0.0172(2) 0.0187(2) 0.00074(18) 0.00389(18) -0.00081(18)
C13 0.0168(2) 0.0252(3) 0.0230(3) -0.0024(2) 0.0030(2) -0.0027(2)
C14 0.0204(3) 0.0222(3) 0.0284(3) -0.0062(2) 0.0057(2) -0.0068(2)
O1 0.0207(2) 0.01364(17) 0.0270(2) -0.00237(16) 0.00613(17) -0.00379(15)
P2 0.01435(8) 0.01366(8) 0.02342(10) 0.0000 0.00094(7) 0.0000
F1 0.0298(2) 0.0257(2) 0.0343(3) -0.0117(2) 0.0005(2) -0.00158(19)
F2 0.0310(3) 0.0267(2) 0.0360(3) 0.0121(2) 0.0009(2) -0.0055(2)
F3 0.01470(17) 0.0348(3) 0.0377(3) 0.0059(2) 0.00385(18) 0.00155(17)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.11574(8)
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
Cu1 . N2 3_656 2.0932(5) yes
Cu1 . N1 3_656 2.0046(6) yes
Cu1 . N1 . 2.0046(6) yes
Cu1 . N2 . 2.0932(5) yes
N1 . C1 . 1.3432(9) yes
N1 . C5 . 1.3527(9) yes
N2 . C6 . 1.3531(8) yes
N2 . C10 . 1.3492(8) yes
C1 . C2 . 1.3906(12) yes
C1 . H11 . 0.935 no
C2 . C3 . 1.3817(16) yes
C2 . H21 . 0.928 no
C3 . C4 . 1.3891(13) yes
C3 . H31 . 0.945 no
C4 . C5 . 1.3940(9) yes
C4 . H41 . 0.944 no
C5 . C6 . 1.4809(9) yes
C6 . C7 . 1.3952(10) yes
C7 . C8 . 1.3869(12) yes
C7 . H71 . 0.930 no
C8 . C9 . 1.3855(11) yes
C8 . H81 . 0.924 no
C9 . C10 . 1.3986(9) yes
C9 . H91 . 0.912 no
C10 . C11 . 1.4554(9) yes
C11 . C12 . 1.3634(9) yes
C11 . O1 . 1.3759(8) yes
C12 . C13 . 1.4298(10) yes
C12 . H121 . 0.916 no
C13 . C14 . 1.3538(12) yes
C13 . H131 . 0.931 no
C14 . O1 . 1.3690(10) yes
C14 . H141 . 0.920 no
P2 . F1 3_756 1.6069(6) yes
P2 . F3 3_756 1.6031(5) yes
P2 . F2 3_756 1.6010(6) yes
P2 . F1 . 1.6069(6) yes
P2 . F2 . 1.6010(6) yes
P2 . F3 . 1.6031(5) 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
N2 3_656 Cu1 . N1 3_656 81.05(2) yes
N2 3_656 Cu1 . N1 . 137.70(2) yes
N1 3_656 Cu1 . N1 . 124.53(4) yes
N2 3_656 Cu1 . N2 . 102.26(3) yes
N1 3_656 Cu1 . N2 . 137.70(2) yes
N1 . Cu1 . N2 . 81.05(2) yes
Cu1 . N1 . C1 . 128.10(5) yes
Cu1 . N1 . C5 . 113.57(4) yes
C1 . N1 . C5 . 118.33(6) yes
Cu1 . N2 . C6 . 109.39(4) yes
Cu1 . N2 . C10 . 129.10(4) yes
C6 . N2 . C10 . 118.17(5) yes
N1 . C1 . C2 . 122.66(8) yes
N1 . C1 . H11 . 117.1 no
C2 . C1 . H11 . 120.2 no
C1 . C2 . C3 . 118.88(8) yes
C1 . C2 . H21 . 119.6 no
C3 . C2 . H21 . 121.5 no
C2 . C3 . C4 . 119.04(7) yes
C2 . C3 . H31 . 120.4 no
C4 . C3 . H31 . 120.5 no
C3 . C4 . C5 . 118.99(8) yes
C3 . C4 . H41 . 119.8 no
C5 . C4 . H41 . 121.2 no
C4 . C5 . N1 . 121.92(7) yes
C4 . C5 . C6 . 122.36(6) yes
N1 . C5 . C6 . 115.69(5) yes
C5 . C6 . N2 . 115.55(6) yes
C5 . C6 . C7 . 121.94(6) yes
N2 . C6 . C7 . 122.50(6) yes
C6 . C7 . C8 . 118.82(6) yes
C6 . C7 . H71 . 121.0 no
C8 . C7 . H71 . 120.2 no
C7 . C8 . C9 . 119.20(7) yes
C7 . C8 . H81 . 121.8 no
C9 . C8 . H81 . 119.0 no
C8 . C9 . C10 . 119.00(7) yes
C8 . C9 . H91 . 121.8 no
C10 . C9 . H91 . 119.2 no
C9 . C10 . N2 . 122.29(6) yes
C9 . C10 . C11 . 120.07(6) yes
N2 . C10 . C11 . 117.57(5) yes
C10 . C11 . C12 . 133.85(6) yes
C10 . C11 . O1 . 116.06(5) yes
C12 . C11 . O1 . 109.80(6) yes
C11 . C12 . C13 . 106.60(6) yes
C11 . C12 . H121 . 124.9 no
C13 . C12 . H121 . 128.4 no
C12 . C13 . C14 . 106.36(6) yes
C12 . C13 . H131 . 128.2 no
C14 . C13 . H131 . 125.4 no
C13 . C14 . O1 . 110.65(6) yes
C13 . C14 . H141 . 131.1 no
O1 . C14 . H141 . 118.2 no
C11 . O1 . C14 . 106.59(6) yes
F1 3_756 P2 . F3 3_756 89.49(3) yes
F1 3_756 P2 . F2 3_756 89.97(4) yes
F3 3_756 P2 . F2 3_756 89.92(3) yes
F1 3_756 P2 . F1 . 89.81(5) yes
F3 3_756 P2 . F1 . 90.09(3) yes
F2 3_756 P2 . F1 . 179.78(4) yes
F1 3_756 P2 . F2 . 179.78(4) yes
F3 3_756 P2 . F2 . 90.50(3) yes
F2 3_756 P2 . F2 . 90.25(5) yes
F1 . P2 . F2 . 89.97(4) yes
F1 3_756 P2 . F3 . 90.09(3) yes
F3 3_756 P2 . F3 . 179.41(5) yes
F2 3_756 P2 . F3 . 90.50(3) yes
F1 . P2 . F3 . 89.49(3) yes
F2 . P2 . F3 . 89.92(3) yes
# Attachment '- pk162.cif'
data_pk162
_database_code_depnum_ccdc_archive 'CCDC 828948'
#TrackingRef '- pk162.cif'
_audit_creation_date 11-01-25
_audit_creation_method CRYSTALS_ver_14.09
_oxford_structure_analysis_title 'pk162f1_123k_0ma in Pna2(1)'
_chemical_name_systematic ?
_chemical_melting_point ?
_cell_length_a 10.715(5)
_cell_length_b 19.191(8)
_cell_length_c 5.731(3)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_volume 1178.4(9)
_symmetry_cell_setting Orthorhombic
_symmetry_space_group_name_H-M 'P n a 21'
_symmetry_space_group_name_Hall 'P 2c -2n'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,y+1/2,z+1/2
x+1/2,-y+1/2,z
-x,-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 0.0033 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'
Se -0.0929 2.2259 17.0006 2.4098 5.8196 0.2726 3.9731 15.2372 4.3543 43.8163
2.8409 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C14 H10 N2 Se1
# Dc = 1.61 Fooo = 568.00 Mu = 31.62 M = 285.21
# Found Formula = C14 H10 N2 Se1
# Dc = 1.61 FOOO = 568.00 Mu = 31.62 M = 285.21
_chemical_formula_sum 'C14 H10 N2 Se1'
_chemical_formula_moiety 'C14 H10 N2 Se1'
_chemical_compound_source ?
_chemical_formula_weight 285.21
_cell_measurement_reflns_used 777
_cell_measurement_theta_min 4
_cell_measurement_theta_max 19
_cell_measurement_temperature 123
_exptl_crystal_description needle
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.010
_exptl_crystal_size_mid 0.020
_exptl_crystal_size_max 0.210
_exptl_crystal_density_diffrn 1.608
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 568
_exptl_absorpt_coefficient_mu 3.162
# Sheldrick geometric approximatio 0.94 0.97
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min 0.94
_exptl_absorpt_correction_T_max 0.97
_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 123
_diffrn_reflns_number 19837
_reflns_number_total 2811
_diffrn_reflns_av_R_equivalents 0.092
# Number of reflections without Friedels Law is 2811
# Number of reflections with Friedels Law is 1544
# Theoretical number of reflections is about 1400
_diffrn_reflns_theta_min 2.122
_diffrn_reflns_theta_max 27.867
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 27.867
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -25
_diffrn_reflns_limit_k_max 25
_diffrn_reflns_limit_l_min -7
_diffrn_reflns_limit_l_max 7
_reflns_limit_h_min 0
_reflns_limit_h_max 14
_reflns_limit_k_min 0
_reflns_limit_k_max 25
_reflns_limit_l_min -7
_reflns_limit_l_max 7
_oxford_diffrn_Wilson_B_factor 0.00
_oxford_diffrn_Wilson_scale 0.00
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -1.01
_refine_diff_density_max 0.41
# 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 1755
_refine_ls_number_restraints 1
_refine_ls_number_parameters 155
_oxford_refine_ls_R_factor_ref 0.0393
_refine_ls_wR_factor_ref 0.0420
_refine_ls_goodness_of_fit_ref 1.1020
_refine_ls_shift/su_max 0.0003185
_refine_ls_shift/su_mean 0.0000151
# The values computed from all data
_oxford_reflns_number_all 2803
_refine_ls_R_factor_all 0.0774
_refine_ls_wR_factor_all 0.0805
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 1973
_refine_ls_R_factor_gt 0.0458
_refine_ls_wR_factor_gt 0.0421
_refine_ls_abs_structure_Flack 0.03(2)
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
# 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 ad
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment none # 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:
0.293 0.156 0.128
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Bruker Analytical X-ray Systems, Inc., 2006. Apex2,
Version 2 User Manual, M86-E01078, Madison, WI.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.
Watkin D.J. (1994).
Acta Cryst, A50, 411-437.
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached 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 0.5595(6) 0.3167(4) 0.0955(13) 0.0368 1.0000 Uani . . . . . .
C2 C 0.4988(5) 0.2782(3) -0.068(2) 0.0334 1.0000 Uani . . . . . .
C3 C 0.3687(5) 0.2744(3) -0.050(2) 0.0324 1.0000 Uani . . . . . .
C4 C 0.3095(6) 0.3092(3) 0.1245(10) 0.0291 1.0000 Uani . . . . . .
C5 C 0.3800(5) 0.3467(3) 0.2829(10) 0.0255 1.0000 Uani . . . . . .
C6 C 0.3196(5) 0.3860(3) 0.4773(11) 0.0226 1.0000 Uani . . . . . .
C7 C 0.3881(5) 0.4276(3) 0.6276(11) 0.0295 1.0000 Uani . . . . . .
C8 C 0.3263(6) 0.4625(4) 0.8067(12) 0.0326 1.0000 Uani . . . . . .
C9 C 0.1999(6) 0.4547(3) 0.8263(11) 0.0299 1.0000 Uani . . . . . .
C10 C 0.1363(5) 0.4136(3) 0.6671(11) 0.0233 1.0000 Uani . . . . . .
C11 C -0.0015(5) 0.4057(3) 0.6752(11) 0.0249 1.0000 Uani . . . . . .
C12 C -0.0852(6) 0.4319(3) 0.8297(10) 0.0278 1.0000 Uani . . . . . .
C13 C -0.2107(5) 0.4156(3) 0.7818(11) 0.0294 1.0000 Uani . . . . . .
C14 C -0.2293(6) 0.3774(3) 0.5872(11) 0.0329 1.0000 Uani . . . . . .
N1 N 0.5047(5) 0.3505(3) 0.2712(9) 0.0322 1.0000 Uani . . . . . .
N2 N 0.1937(4) 0.3795(3) 0.4964(7) 0.0225 1.0000 Uani . . . . . .
Se1 Se -0.07948(4) 0.35534(3) 0.4384(3) 0.0277 1.0000 Uani . . . . . .
H11 H 0.6469 0.3185 0.0879 0.0402 1.0000 Uiso R . . . . .
H21 H 0.5410 0.2571 -0.1941 0.0381 1.0000 Uiso R . . . . .
H31 H 0.3218 0.2467 -0.1537 0.0395 1.0000 Uiso R . . . . .
H41 H 0.2226 0.3086 0.1370 0.0351 1.0000 Uiso R . . . . .
H71 H 0.4748 0.4323 0.6075 0.0340 1.0000 Uiso R . . . . .
H81 H 0.3722 0.4907 0.9083 0.0361 1.0000 Uiso R . . . . .
H91 H 0.1565 0.4777 0.9456 0.0393 1.0000 Uiso R . . . . .
H121 H -0.0615 0.4590 0.9594 0.0338 1.0000 Uiso R . . . . .
H131 H -0.2763 0.4302 0.8760 0.0371 1.0000 Uiso R . . . . .
H141 H -0.3079 0.3634 0.5337 0.0382 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 0.020(3) 0.036(4) 0.054(4) 0.014(3) 0.009(3) 0.000(3)
C2 0.029(2) 0.037(3) 0.034(3) -0.011(5) 0.007(6) -0.002(2)
C3 0.033(2) 0.035(3) 0.030(3) 0.000(5) -0.005(5) -0.006(2)
C4 0.023(3) 0.039(4) 0.026(3) -0.005(3) 0.009(2) 0.001(2)
C5 0.022(2) 0.027(4) 0.027(3) 0.003(3) -0.001(2) 0.003(2)
C6 0.014(2) 0.030(3) 0.024(5) 0.002(2) 0.002(2) -0.0009(19)
C7 0.021(3) 0.029(4) 0.039(3) -0.001(3) -0.005(2) -0.003(2)
C8 0.025(3) 0.035(4) 0.038(4) -0.014(3) -0.011(3) 0.005(3)
C9 0.025(3) 0.036(4) 0.028(3) -0.001(3) -0.001(2) 0.002(3)
C10 0.017(3) 0.022(3) 0.031(3) 0.004(2) -0.002(2) 0.004(2)
C11 0.016(2) 0.030(4) 0.028(3) 0.005(3) 0.004(2) 0.002(2)
C12 0.024(3) 0.033(3) 0.027(2) -0.003(2) 0.001(3) -0.002(3)
C13 0.017(3) 0.037(4) 0.034(3) 0.006(3) 0.007(2) 0.005(3)
C14 0.024(3) 0.040(4) 0.035(3) 0.008(3) 0.000(3) -0.004(3)
N1 0.019(2) 0.041(3) 0.037(3) 0.002(3) 0.000(2) 0.003(2)
N2 0.0151(18) 0.024(2) 0.028(3) 0.0045(17) 0.0013(16) 0.0040(17)
Se1 0.01992(19) 0.0385(3) 0.0248(2) -0.0043(5) -0.0003(6) -0.0023(3)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.1373(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.359(12) yes
C1 . N1 . 1.333(9) yes
C1 . H11 . 0.938 no
C2 . C3 . 1.401(7) yes
C2 . H21 . 0.943 no
C3 . C4 . 1.361(12) yes
C3 . H31 . 0.942 no
C4 . C5 . 1.382(9) yes
C4 . H41 . 0.934 no
C5 . C6 . 1.493(9) yes
C5 . N1 . 1.340(8) yes
C6 . C7 . 1.385(8) yes
C6 . N2 . 1.359(6) yes
C7 . C8 . 1.393(9) yes
C7 . H71 . 0.941 no
C8 . C9 . 1.367(8) yes
C8 . H81 . 0.934 no
C9 . C10 . 1.385(9) yes
C9 . H91 . 0.937 no
C10 . C11 . 1.485(8) yes
C10 . N2 . 1.328(8) yes
C11 . C12 . 1.357(8) yes
C11 . Se1 . 1.864(7) yes
C12 . C13 . 1.408(9) yes
C12 . H121 . 0.943 no
C13 . C14 . 1.349(9) yes
C13 . H131 . 0.930 no
C14 . Se1 . 1.866(7) yes
C14 . H141 . 0.935 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . N1 . 125.0(6) yes
C2 . C1 . H11 . 117.7 no
N1 . C1 . H11 . 117.2 no
C1 . C2 . C3 . 117.0(9) yes
C1 . C2 . H21 . 122.2 no
C3 . C2 . H21 . 120.7 no
C2 . C3 . C4 . 119.5(9) yes
C2 . C3 . H31 . 121.0 no
C4 . C3 . H31 . 119.5 no
C3 . C4 . C5 . 119.0(6) yes
C3 . C4 . H41 . 120.9 no
C5 . C4 . H41 . 120.1 no
C4 . C5 . C6 . 121.1(5) yes
C4 . C5 . N1 . 122.7(6) yes
C6 . C5 . N1 . 116.2(6) yes
C5 . C6 . C7 . 121.8(5) yes
C5 . C6 . N2 . 116.3(5) yes
C7 . C6 . N2 . 121.9(6) yes
C6 . C7 . C8 . 119.0(5) yes
C6 . C7 . H71 . 120.1 no
C8 . C7 . H71 . 120.9 no
C7 . C8 . C9 . 118.6(6) yes
C7 . C8 . H81 . 119.1 no
C9 . C8 . H81 . 122.3 no
C8 . C9 . C10 . 119.7(6) yes
C8 . C9 . H91 . 119.9 no
C10 . C9 . H91 . 120.4 no
C9 . C10 . C11 . 121.8(6) yes
C9 . C10 . N2 . 122.6(5) yes
C11 . C10 . N2 . 115.7(6) yes
C10 . C11 . C12 . 129.8(6) yes
C10 . C11 . Se1 . 118.4(5) yes
C12 . C11 . Se1 . 111.7(4) yes
C11 . C12 . C13 . 115.0(6) yes
C11 . C12 . H121 . 122.7 no
C13 . C12 . H121 . 122.3 no
C12 . C13 . C14 . 115.0(6) yes
C12 . C13 . H131 . 122.8 no
C14 . C13 . H131 . 122.2 no
C13 . C14 . Se1 . 112.0(5) yes
C13 . C14 . H141 . 124.0 no
Se1 . C14 . H141 . 124.0 no
C5 . N1 . C1 . 116.8(6) yes
C6 . N2 . C10 . 118.3(5) yes
C14 . Se1 . C11 . 86.3(3) 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
C14 . H141 . N1 1_455 160 0.94 2.52 3.416(9) yes
# Attachment '- pk60.cif'
data_pk60
_database_code_depnum_ccdc_archive 'CCDC 828949'
#TrackingRef '- pk60.cif'
_publ_section_exptl_refinement
# Some potentially useful phrases are donated by Bill Clegg:
;
In the absence of significant anomalous scattering, Friedel pairs were
merged.
The absolute configuration was arbitrarily assigned.
The relatively large ratio of minimum to maximum corrections applied
in the multiscan process (1:nnn) reflect changes in the illuminated
volume of the crystal.
Changes in illuminated volume were kept to a minimum, and were
taken into account (G\"orbitz, 1999) by the multi-scan inter-frame
scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).
G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.
The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry
(C---H in the range 0.93--0.98,
N---H in the range 0.86--0.89
N---H to 0.86
O---H = 0.82
\%A)
and
U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom),
after which the positions were refined with riding constraints.
;
_publ_section_exptl_prep
# Brief details or a reference. Include solvent if known
;
?
;
# Hand-made tables can be put in the cif. The number of columns
# is set in the loop header.
# The contants of each column can either be a piece of text
# without any spaces (eg a number) or other text enclosed in " "
# Remove the leading # in the following example
#geom_extra_table_head_A
#;
#Table 2.
#Molecular parameters deviating most from MOGUL averages
#;
#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
#_geom_extra_tableA_col_4
#
#Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d"
#N5-C6-C4 129 124 "7 (\%)"
#C3-O10-C2 105 109 "2 (\%)"
#C6-O7 1.25 1.22 ".02 (\%A)"
#
# End of 'script/refcif-b.dat'
#end of refcif
_cell_length_a 7.1898(2)
_cell_length_b 14.0902(3)
_cell_length_c 14.6598(4)
_cell_angle_alpha 103.270(2)
_cell_angle_beta 99.206(2)
_cell_angle_gamma 98.373(2)
_cell_volume 1400.92(7)
_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'
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'
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'
Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 2
# Given Formula = C28 H20 Cu1 F6 N4 P1 S2
# Dc = 1.62 Fooo = 692.00 Mu = 10.53 M = 685.13
# Found Formula = C28 H20 Cu1 F6 N4 P1 S2
# Dc = 1.62 FOOO = 692.00 Mu = 10.53 M = 685.13
_chemical_formula_sum 'C28 H20 Cu1 F6 N4 P1 S2'
_chemical_formula_moiety 'C28 H20 Cu N4 S2, F6 P'
_chemical_compound_source ?
_chemical_formula_weight 685.13
_cell_measurement_reflns_used 4686
_cell_measurement_theta_min 4
_cell_measurement_theta_max 30
_cell_measurement_temperature 123
_exptl_crystal_description block
_exptl_crystal_colour red
_exptl_crystal_size_min 0.08
_exptl_crystal_size_mid 0.19
_exptl_crystal_size_max 0.31
_exptl_crystal_density_diffrn 1.624
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 692
_exptl_absorpt_coefficient_mu 1.053
# Sheldrick geometric approximatio 0.82 0.92
# No experimental values of Tmin/max available
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min 0.82
_exptl_absorpt_correction_T_max 0.92
_diffrn_measurement_device 'Bruker Kappa Apex2'
_diffrn_measurement_device_type 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 123
_diffrn_reflns_number 22905
_reflns_number_total 7740
_diffrn_reflns_av_R_equivalents 0.046
# Number of reflections with Friedels Law is 7740
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 7860
_diffrn_reflns_theta_min 1.808
_diffrn_reflns_theta_max 29.574
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full 25.434
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -19
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_limit_l_max 20
_reflns_limit_h_min -9
_reflns_limit_h_max 9
_reflns_limit_k_min -19
_reflns_limit_k_max 19
_reflns_limit_l_min 0
_reflns_limit_l_max 20
_oxford_diffrn_Wilson_B_factor 1.66
_oxford_diffrn_Wilson_scale 59.75
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.64
_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>3.0\s(I)
_refine_ls_number_reflns 4821
_refine_ls_number_restraints 114
_refine_ls_number_parameters 404
_oxford_refine_ls_R_factor_ref 0.0404
_refine_ls_wR_factor_ref 0.0389
_refine_ls_goodness_of_fit_ref 1.0610
_refine_ls_shift/su_max 0.024538
# The values computed from all data
_oxford_reflns_number_all 7724
_refine_ls_R_factor_all 0.0770
_refine_ls_wR_factor_all 0.0696
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 5144
_refine_ls_R_factor_gt 0.0434
_refine_ls_wR_factor_gt 0.0403
# 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:
0.244 0.151 0.114
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.
Watkin D.J. (1994).
Acta Cryst, A50, 411-437.
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
Bruker Analytical X-ray Systems, Inc., 2006. Apex2,
Version 2 User Manual, M86-E01078, Madison, WI.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.37744(5) 0.18093(2) 0.12853(2) 0.0206 1.0000 Uani . . . . . . .
N1 N 0.4766(3) 0.27748(17) 0.06058(16) 0.0204 1.0000 Uani . . . . . . .
N2 N 0.6377(3) 0.26098(16) 0.23459(14) 0.0162 1.0000 Uani . . . . . . .
N3 N 0.2615(3) 0.03634(16) 0.07487(16) 0.0191 1.0000 Uani . . . . . . .
N4 N 0.2112(3) 0.16268(16) 0.23056(15) 0.0165 1.0000 Uani . . . . . . .
C1 C 0.4262(4) 0.2728(2) -0.0328(2) 0.0272 1.0000 Uani . . . . . . .
C2 C 0.5128(5) 0.3405(3) -0.0755(2) 0.0381 1.0000 Uani . . . . . . .
C3 C 0.6585(5) 0.4161(3) -0.0194(2) 0.0390 1.0000 Uani . . . . . . .
C4 C 0.7131(4) 0.4223(2) 0.0772(2) 0.0296 1.0000 Uani . . . . . . .
C5 C 0.6206(4) 0.3515(2) 0.11493(18) 0.0203 1.0000 Uani . . . . . . .
C6 C 0.6748(4) 0.35079(19) 0.21664(18) 0.0181 1.0000 Uani . . . . . . .
C7 C 0.7595(4) 0.4375(2) 0.2870(2) 0.0232 1.0000 Uani . . . . . . .
C8 C 0.8114(4) 0.4306(2) 0.3802(2) 0.0253 1.0000 Uani . . . . . . .
C9 C 0.7814(4) 0.3397(2) 0.39974(19) 0.0238 1.0000 Uani . . . . . . .
C10 C 0.6937(4) 0.2548(2) 0.32523(17) 0.0187 1.0000 Uani . . . . . . .
C11 C 0.6663(4) 0.1566(2) 0.34403(19) 0.0216 1.0000 Uani . . . . . . .
C12 C 0.6694(4) 0.1333(2) 0.4319(2) 0.0274 1.0000 Uani . . . . . . .
C13 C 0.6549(5) 0.0317(3) 0.4230(3) 0.0392 1.0000 Uani . . . . . . .
C14 C 0.6393(5) -0.0230(3) 0.3321(3) 0.0365 1.0000 Uani . . . . . . .
S1 S 0.64537(10) 0.05056(5) 0.25408(5) 0.0251 1.0000 Uani . . . . . . .
C21 C 0.2619(4) -0.0219(2) -0.01143(19) 0.0217 1.0000 Uani . . . . . . .
C22 C 0.1839(4) -0.1225(2) -0.0397(2) 0.0250 1.0000 Uani . . . . . . .
C23 C 0.1041(4) -0.1647(2) 0.0252(2) 0.0298 1.0000 Uani . . . . . . .
C24 C 0.1008(4) -0.1051(2) 0.1145(2) 0.0250 1.0000 Uani . . . . . . .
C25 C 0.1791(4) -0.00483(19) 0.13688(18) 0.0174 1.0000 Uani . . . . . . .
C26 C 0.1747(3) 0.06542(19) 0.22903(18) 0.0176 1.0000 Uani . . . . . . .
C27 C 0.1394(4) 0.0334(2) 0.30857(19) 0.0211 1.0000 Uani . . . . . . .
C28 C 0.1362(4) 0.1032(2) 0.39134(19) 0.0225 1.0000 Uani . . . . . . .
C29 C 0.1676(4) 0.2026(2) 0.39306(18) 0.0214 1.0000 Uani . . . . . . .
C30 C 0.2052(3) 0.23095(19) 0.31124(18) 0.0174 1.0000 Uani . . . . . . .
C31 C 0.2392(4) 0.336095(19) 0.31050(3) 0.0239 1.0000 Uani D U . . . . .
C32 C 0.3081(4) 0.41979(3) 0.38996(3) 0.0242 0.869(2) Uani D U P . . . .
C33 C 0.3120(4) 0.50972(3) 0.36160(4) 0.0271 0.869(2) Uani D U P . . . .
C34 C 0.2479(4) 0.49543(2) 0.26668(6) 0.0272 0.869(2) Uani D U P . . . .
S2 S 0.18454(11) 0.37304(3) 0.20767(3) 0.0256 0.869(2) Uani D U P . . . .
C42 C 0.2208(4) 0.37519(3) 0.22933(3) 0.0246 0.131(2) Uani D U P . . . .
C43 C 0.2712(4) 0.48043(3) 0.25634(4) 0.0261 0.131(2) Uani D U P . . . .
C44 C 0.3306(4) 0.51884(2) 0.35179(6) 0.0264 0.131(2) Uani D U P . . . .
S12 S 0.32154(11) 0.42978(3) 0.41294(3) 0.0257 0.131(2) Uani D U P . . . .
P1 P 0.07217(11) 0.26776(5) -0.31105(5) 0.0241 1.0000 Uani . . . . . . .
F1 F 0.1582(3) 0.20659(12) -0.23934(12) 0.0285 1.0000 Uani . . . . . . .
F2 F -0.0111(3) 0.32950(14) -0.38193(14) 0.0470 1.0000 Uani . . . . . . .
F3 F 0.0622(3) 0.35472(14) -0.22115(14) 0.0455 1.0000 Uani . . . . . . .
F4 F 0.2842(3) 0.32070(19) -0.30887(18) 0.0547 1.0000 Uani . . . . . . .
F5 F 0.0782(4) 0.18039(16) -0.39964(14) 0.0551 1.0000 Uani . . . . . . .
F6 F -0.1398(3) 0.21565(17) -0.31035(18) 0.0512 1.0000 Uani . . . . . . .
H11 H 0.3280 0.2208 -0.0706 0.0334 1.0000 Uiso R . . . . . .
H21 H 0.4754 0.3358 -0.1411 0.0449 1.0000 Uiso R . . . . . .
H31 H 0.7209 0.4628 -0.0463 0.0472 1.0000 Uiso R . . . . . .
H41 H 0.8099 0.4728 0.1170 0.0353 1.0000 Uiso R . . . . . .
H71 H 0.7775 0.4977 0.2715 0.0262 1.0000 Uiso R . . . . . .
H81 H 0.8668 0.4874 0.4295 0.0292 1.0000 Uiso R . . . . . .
H91 H 0.8197 0.3335 0.4614 0.0271 1.0000 Uiso R . . . . . .
H121 H 0.6806 0.1814 0.4906 0.0370 1.0000 Uiso R . . . . . .
H131 H 0.6558 0.0037 0.4761 0.0539 1.0000 Uiso R . . . . . .
H141 H 0.6263 -0.0932 0.3142 0.0510 1.0000 Uiso R . . . . . .
H211 H 0.3190 0.0083 -0.0543 0.0260 1.0000 Uiso R . . . . . .
H221 H 0.1870 -0.1602 -0.1008 0.0283 1.0000 Uiso R . . . . . .
H231 H 0.0537 -0.2322 0.0097 0.0343 1.0000 Uiso R . . . . . .
H241 H 0.0468 -0.1320 0.1595 0.0285 1.0000 Uiso R . . . . . .
H271 H 0.1175 -0.0334 0.3056 0.0261 1.0000 Uiso R . . . . . .
H281 H 0.1115 0.0832 0.4458 0.0284 1.0000 Uiso R . . . . . .
H291 H 0.1619 0.2511 0.4479 0.0275 1.0000 Uiso R . . . . . .
H321 H 0.3484 0.4162 0.4539 0.0265 0.8569 Uiso . . . . . . .
H331 H 0.3545 0.5736 0.4050 0.0288 0.8569 Uiso . . . . . . .
H341 H 0.2393 0.5478 0.2362 0.0294 0.8569 Uiso . . . . . . .
H421 H 0.1780 0.3360 0.1652 0.0262 0.1431 Uiso . . . . . . .
H431 H 0.2648 0.5198 0.2117 0.0279 0.1431 Uiso . . . . . . .
H441 H 0.3726 0.5878 0.3816 0.0284 0.1431 Uiso . . . . . . .
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
Cu1 0.02265(17) 0.01882(16) 0.01916(16) 0.00420(12) 0.00606(13) -0.00097(12)
N1 0.0206(11) 0.0226(11) 0.0175(10) 0.0067(8) 0.0006(8) 0.0034(9)
N2 0.0143(10) 0.0203(10) 0.0140(9) 0.0049(8) 0.0016(8) 0.0037(8)
N3 0.0163(10) 0.0205(11) 0.0199(10) 0.0042(8) 0.0036(8) 0.0035(8)
N4 0.0136(10) 0.0194(10) 0.0159(10) 0.0040(8) 0.0015(8) 0.0035(8)
C1 0.0273(14) 0.0313(15) 0.0204(13) 0.0103(11) -0.0019(11) -0.0014(12)
C2 0.0420(18) 0.050(2) 0.0224(14) 0.0214(14) -0.0025(13) -0.0007(15)
C3 0.0430(19) 0.0392(18) 0.0365(18) 0.0239(15) 0.0038(14) -0.0045(15)
C4 0.0320(15) 0.0273(15) 0.0263(14) 0.0124(12) -0.0021(12) -0.0048(12)
C5 0.0213(12) 0.0208(12) 0.0173(12) 0.0045(10) 0.0012(10) 0.0028(10)
C6 0.0146(11) 0.0211(12) 0.0160(11) 0.0014(9) 0.0005(9) 0.0038(9)
C7 0.0210(13) 0.0212(13) 0.0248(13) 0.0033(10) 0.0012(10) 0.0039(10)
C8 0.0205(13) 0.0281(14) 0.0207(13) -0.0031(11) -0.0022(10) 0.0054(11)
C9 0.0169(12) 0.0384(16) 0.0148(12) 0.0051(11) -0.0008(9) 0.0081(11)
C10 0.0147(11) 0.0270(13) 0.0149(11) 0.0056(9) 0.0014(9) 0.0067(10)
C11 0.0157(12) 0.0323(14) 0.0210(12) 0.0132(11) 0.0043(10) 0.0071(10)
C12 0.0200(13) 0.0455(18) 0.0224(13) 0.0147(12) 0.0042(11) 0.0152(12)
C13 0.0305(16) 0.064(2) 0.0430(19) 0.0389(18) 0.0163(14) 0.0212(16)
C14 0.0294(16) 0.0340(17) 0.060(2) 0.0299(16) 0.0145(15) 0.0141(13)
S1 0.0246(3) 0.0260(3) 0.0279(3) 0.0114(3) 0.0048(3) 0.0083(3)
C21 0.0206(12) 0.0267(13) 0.0176(12) 0.0037(10) 0.0054(10) 0.0050(10)
C22 0.0237(14) 0.0248(14) 0.0211(13) -0.0029(10) -0.0007(11) 0.0074(11)
C23 0.0308(16) 0.0218(14) 0.0324(16) 0.0024(11) 0.0028(12) 0.0022(11)
C24 0.0275(14) 0.0194(13) 0.0264(14) 0.0036(10) 0.0058(11) 0.0021(11)
C25 0.0144(11) 0.0207(12) 0.0170(11) 0.0048(9) 0.0020(9) 0.0039(9)
C26 0.0143(11) 0.0212(12) 0.0181(11) 0.0063(9) 0.0035(9) 0.0033(9)
C27 0.0199(12) 0.0235(13) 0.0220(13) 0.0088(10) 0.0044(10) 0.0058(10)
C28 0.0207(13) 0.0329(15) 0.0194(12) 0.0128(11) 0.0064(10) 0.0101(11)
C29 0.0204(12) 0.0297(14) 0.0148(11) 0.0033(10) 0.0045(9) 0.0097(10)
C30 0.0111(11) 0.0226(12) 0.0182(12) 0.0041(9) 0.0016(9) 0.0053(9)
C31 0.0247(6) 0.0229(6) 0.0246(6) 0.0040(5) 0.0055(6) 0.0091(5)
C32 0.0242(7) 0.0234(7) 0.0245(7) 0.0020(6) 0.0057(7) 0.0084(6)
C33 0.0271(7) 0.0240(7) 0.0290(7) 0.0023(6) 0.0064(7) 0.0076(7)
C34 0.0281(7) 0.0240(6) 0.0295(7) 0.0042(6) 0.0061(6) 0.0087(6)
S2 0.0280(4) 0.0237(4) 0.0255(4) 0.0056(3) 0.0044(3) 0.0084(3)
C42 0.0253(8) 0.0233(8) 0.0253(8) 0.0035(7) 0.0058(8) 0.0086(8)
C43 0.0266(8) 0.0237(8) 0.0277(8) 0.0032(8) 0.0063(8) 0.0083(8)
C44 0.0272(8) 0.0239(7) 0.0279(8) 0.0038(7) 0.0060(8) 0.0083(7)
S12 0.0265(7) 0.0240(7) 0.0262(7) 0.0037(6) 0.0054(7) 0.0082(7)
P1 0.0360(4) 0.0175(3) 0.0167(3) 0.0051(3) -0.0018(3) 0.0051(3)
F1 0.0373(9) 0.0255(8) 0.0234(8) 0.0122(7) 0.0005(7) 0.0049(7)
F2 0.0737(15) 0.0304(10) 0.0317(10) 0.0133(8) -0.0152(10) 0.0137(10)
F3 0.0746(15) 0.0269(10) 0.0294(10) -0.0014(8) 0.0012(10) 0.0156(10)
F4 0.0440(12) 0.0683(16) 0.0631(15) 0.0436(13) 0.0123(11) 0.0018(11)
F5 0.107(2) 0.0411(12) 0.0198(9) 0.0032(8) 0.0072(11) 0.0344(12)
F6 0.0353(11) 0.0463(13) 0.0682(15) 0.0219(11) -0.0036(10) -0.0005(9)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.13181(16)
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
Cu1 . N1 . 1.980(2) yes
Cu1 . N2 . 2.200(2) yes
Cu1 . N3 . 2.006(2) yes
Cu1 . N4 . 2.095(2) yes
N1 . C1 . 1.343(3) yes
N1 . C5 . 1.354(3) yes
N2 . C6 . 1.349(3) yes
N2 . C10 . 1.352(3) yes
N3 . C21 . 1.341(3) yes
N3 . C25 . 1.352(3) yes
N4 . C26 . 1.352(3) yes
N4 . C30 . 1.354(3) yes
C1 . C2 . 1.383(4) yes
C1 . H11 . 0.938 no
C2 . C3 . 1.380(5) yes
C2 . H21 . 0.941 no
C3 . C4 . 1.387(4) yes
C3 . H31 . 0.938 no
C4 . C5 . 1.387(4) yes
C4 . H41 . 0.931 no
C5 . C6 . 1.482(4) yes
C6 . C7 . 1.390(4) yes
C7 . C8 . 1.387(4) yes
C7 . H71 . 0.924 no
C8 . C9 . 1.371(4) yes
C8 . H81 . 0.933 no
C9 . C10 . 1.408(4) yes
C9 . H91 . 0.929 no
C10 . C11 . 1.464(4) yes
C11 . C12 . 1.398(4) yes
C11 . S1 . 1.720(3) yes
C12 . C13 . 1.395(5) yes
C12 . H121 . 0.950 no
C13 . C14 . 1.355(5) yes
C13 . H131 . 0.950 no
C14 . S1 . 1.712(3) yes
C14 . H141 . 0.950 no
C21 . C22 . 1.386(4) yes
C21 . H211 . 0.948 no
C22 . C23 . 1.386(4) yes
C22 . H221 . 0.936 no
C23 . C24 . 1.390(4) yes
C23 . H231 . 0.928 no
C24 . C25 . 1.384(4) yes
C24 . H241 . 0.940 no
C25 . C26 . 1.488(4) yes
C26 . C27 . 1.389(4) yes
C27 . C28 . 1.381(4) yes
C27 . H271 . 0.922 no
C28 . C29 . 1.380(4) yes
C28 . H281 . 0.939 no
C29 . C30 . 1.401(4) yes
C29 . H291 . 0.939 no
C30 . C31 . 1.469(3) yes
C31 . C32 . 1.4168(6) yes
C31 . S2 . 1.7111(6) yes
C31 . C42 . 1.4172(6) yes
C31 . S12 . 1.7107(6) yes
C32 . C33 . 1.4192(5) yes
C32 . H321 . 0.951 no
C33 . C34 . 1.3523(5) yes
C33 . H331 . 0.951 no
C34 . S2 . 1.7001(4) yes
C34 . H341 . 0.951 no
C42 . C43 . 1.4195(4) yes
C42 . H421 . 0.951 no
C43 . C44 . 1.3516(5) yes
C43 . H431 . 0.950 no
C44 . S12 . 1.7011(5) yes
C44 . H441 . 0.951 no
P1 . F1 . 1.6105(17) yes
P1 . F2 . 1.6009(19) yes
P1 . F3 . 1.599(2) yes
P1 . F4 . 1.589(2) yes
P1 . F5 . 1.582(2) yes
P1 . F6 . 1.595(2) 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
N1 . Cu1 . N2 . 80.41(8) yes
N1 . Cu1 . N3 . 128.44(9) yes
N2 . Cu1 . N3 . 133.10(8) yes
N1 . Cu1 . N4 . 143.07(9) yes
N2 . Cu1 . N4 . 94.74(8) yes
N3 . Cu1 . N4 . 80.97(9) yes
Cu1 . N1 . C1 . 127.17(19) yes
Cu1 . N1 . C5 . 114.53(17) yes
C1 . N1 . C5 . 118.1(2) yes
Cu1 . N2 . C6 . 104.80(15) yes
Cu1 . N2 . C10 . 128.89(17) yes
C6 . N2 . C10 . 118.0(2) yes
Cu1 . N3 . C21 . 128.00(19) yes
Cu1 . N3 . C25 . 113.50(17) yes
C21 . N3 . C25 . 118.5(2) yes
Cu1 . N4 . C26 . 108.79(16) yes
Cu1 . N4 . C30 . 127.21(17) yes
C26 . N4 . C30 . 118.7(2) yes
N1 . C1 . C2 . 123.1(3) yes
N1 . C1 . H11 . 118.0 no
C2 . C1 . H11 . 118.9 no
C1 . C2 . C3 . 118.4(3) yes
C1 . C2 . H21 . 121.8 no
C3 . C2 . H21 . 119.8 no
C2 . C3 . C4 . 119.5(3) yes
C2 . C3 . H31 . 120.5 no
C4 . C3 . H31 . 120.0 no
C3 . C4 . C5 . 118.9(3) yes
C3 . C4 . H41 . 121.5 no
C5 . C4 . H41 . 119.5 no
C4 . C5 . N1 . 121.9(2) yes
C4 . C5 . C6 . 122.3(2) yes
N1 . C5 . C6 . 115.8(2) yes
C5 . C6 . N2 . 115.3(2) yes
C5 . C6 . C7 . 121.3(2) yes
N2 . C6 . C7 . 123.4(2) yes
C6 . C7 . C8 . 118.0(3) yes
C6 . C7 . H71 . 120.1 no
C8 . C7 . H71 . 121.8 no
C7 . C8 . C9 . 119.6(3) yes
C7 . C8 . H81 . 120.5 no
C9 . C8 . H81 . 119.9 no
C8 . C9 . C10 . 119.5(2) yes
C8 . C9 . H91 . 120.7 no
C10 . C9 . H91 . 119.8 no
C9 . C10 . N2 . 121.4(2) yes
C9 . C10 . C11 . 120.3(2) yes
N2 . C10 . C11 . 118.3(2) yes
C10 . C11 . C12 . 128.3(3) yes
C10 . C11 . S1 . 121.10(19) yes
C12 . C11 . S1 . 110.3(2) yes
C11 . C12 . C13 . 112.1(3) yes
C11 . C12 . H121 . 123.6 no
C13 . C12 . H121 . 124.3 no
C12 . C13 . C14 . 113.9(3) yes
C12 . C13 . H131 . 122.6 no
C14 . C13 . H131 . 123.4 no
C13 . C14 . S1 . 111.4(3) yes
C13 . C14 . H141 . 124.1 no
S1 . C14 . H141 . 124.5 no
C11 . S1 . C14 . 92.14(16) yes
N3 . C21 . C22 . 123.1(3) yes
N3 . C21 . H211 . 117.4 no
C22 . C21 . H211 . 119.5 no
C21 . C22 . C23 . 118.1(3) yes
C21 . C22 . H221 . 120.1 no
C23 . C22 . H221 . 121.8 no
C22 . C23 . C24 . 119.4(3) yes
C22 . C23 . H231 . 120.8 no
C24 . C23 . H231 . 119.8 no
C23 . C24 . C25 . 119.0(3) yes
C23 . C24 . H241 . 120.9 no
C25 . C24 . H241 . 120.1 no
C24 . C25 . N3 . 121.8(2) yes
C24 . C25 . C26 . 122.8(2) yes
N3 . C25 . C26 . 115.3(2) yes
C25 . C26 . N4 . 115.3(2) yes
C25 . C26 . C27 . 122.4(2) yes
N4 . C26 . C27 . 122.3(2) yes
C26 . C27 . C28 . 118.9(3) yes
C26 . C27 . H271 . 120.2 no
C28 . C27 . H271 . 120.9 no
C27 . C28 . C29 . 119.4(2) yes
C27 . C28 . H281 . 120.3 no
C29 . C28 . H281 . 120.3 no
C28 . C29 . C30 . 119.3(2) yes
C28 . C29 . H291 . 120.8 no
C30 . C29 . H291 . 119.9 no
C29 . C30 . N4 . 121.3(2) yes
C29 . C30 . C31 . 120.8(2) yes
N4 . C30 . C31 . 117.9(2) yes
C30 . C31 . C32 . 127.56(10) yes
C30 . C31 . S2 . 121.95(10) yes
C32 . C31 . S2 . 110.405(9) yes
C30 . C31 . C42 . 127.18(10) yes
C32 . C31 . C42 . 105.16(2) yes
C30 . C31 . S12 . 122.34(10) yes
S2 . C31 . S12 . 115.59(2) yes
C42 . C31 . S12 . 110.399(9) yes
C31 . C32 . C33 . 111.263(9) yes
C31 . C32 . H321 . 124.4 no
C33 . C32 . H321 . 124.3 no
C32 . C33 . C34 . 113.245(9) yes
C32 . C33 . H331 . 123.4 no
C34 . C33 . H331 . 123.4 no
C33 . C34 . S2 . 112.387(9) yes
C33 . C34 . H341 . 124.0 no
S2 . C34 . H341 . 123.6 no
C31 . S2 . C34 . 92.690(9) yes
C31 . C42 . C43 . 111.261(9) yes
C31 . C42 . H421 . 124.3 no
C43 . C42 . H421 . 124.4 no
C42 . C43 . C44 . 113.239(9) yes
C42 . C43 . H431 . 123.3 no
C44 . C43 . H431 . 123.4 no
C43 . C44 . S12 . 112.383(9) yes
C43 . C44 . H441 . 124.0 no
S12 . C44 . H441 . 123.7 no
C31 . S12 . C44 . 92.684(9) yes
F1 . P1 . F2 . 179.33(12) yes
F1 . P1 . F3 . 89.72(10) yes
F2 . P1 . F3 . 90.03(11) yes
F1 . P1 . F4 . 89.44(11) yes
F2 . P1 . F4 . 89.93(12) yes
F3 . P1 . F4 . 89.38(14) yes
F1 . P1 . F5 . 89.99(10) yes
F2 . P1 . F5 . 90.27(11) yes
F3 . P1 . F5 . 178.82(14) yes
F4 . P1 . F5 . 91.75(15) yes
F1 . P1 . F6 . 89.78(11) yes
F2 . P1 . F6 . 90.84(13) yes
F3 . P1 . F6 . 89.38(13) yes
F4 . P1 . F6 . 178.54(14) yes
F5 . P1 . F6 . 89.48(14) yes
# Attachment '- pk64.cif'
data_pk64
_database_code_depnum_ccdc_archive 'CCDC 828950'
#TrackingRef '- pk64.cif'
_publ_section_exptl_refinement
# Some potentially useful phrases are donated by Bill Clegg:
;
In the absence of significant anomalous scattering, Friedel pairs were
merged.
The absolute configuration was arbitrarily assigned.
The relatively large ratio of minimum to maximum corrections applied
in the multiscan process (1:nnn) reflect changes in the illuminated
volume of the crystal.
Changes in illuminated volume were kept to a minimum, and were
taken into account (G\"orbitz, 1999) by the multi-scan inter-frame
scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).
G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.
The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry
(C---H in the range 0.93--0.98,
N---H in the range 0.86--0.89
N---H to 0.86
O---H = 0.82
\%A)
and
U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom),
after which the positions were refined with riding constraints.
;
_publ_section_exptl_prep
# Brief details or a reference. Include solvent if known
;
?
;
# Hand-made tables can be put in the cif. The number of columns
# is set in the loop header.
# The contants of each column can either be a piece of text
# without any spaces (eg a number) or other text enclosed in " "
# Remove the leading # in the following example
#geom_extra_table_head_A
#;
#Table 2.
#Molecular parameters deviating most from MOGUL averages
#;
#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
#_geom_extra_tableA_col_4
#
#Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d"
#N5-C6-C4 129 124 "7 (\%)"
#C3-O10-C2 105 109 "2 (\%)"
#C6-O7 1.25 1.22 ".02 (\%A)"
#
# End of 'script/refcif-b.dat'
#end of refcif
_cell_length_a 15.5702(6)
_cell_length_b 12.5528(5)
_cell_length_c 15.1905(6)
_cell_angle_alpha 90
_cell_angle_beta 102.575(2)
_cell_angle_gamma 90
_cell_volume 2897.8(2)
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'C 2/c'
_symmetry_space_group_name_Hall '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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'
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'
Cu 0.3201 1.2651 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C30 H24 Cu1 F6 N6 P1
# Dc = 1.55 Fooo = 1384.00 Mu = 8.80 M = 338.53
# Found Formula = C30 H26 Cu1 F6 N6 P1
# Dc = 1.56 FOOO = 1384.00 Mu = 8.80 M = 339.54
_chemical_formula_sum 'C30 H26 Cu1 F6 N6 P1'
_chemical_formula_moiety 'C30 H26 Cu N6, F6 P'
_chemical_compound_source ?
_chemical_formula_weight 679.08
_cell_measurement_reflns_used 9776
_cell_measurement_theta_min 3
_cell_measurement_theta_max 38
_cell_measurement_temperature 123
_exptl_crystal_description block
_exptl_crystal_colour red
_exptl_crystal_size_min 0.09
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_max 0.19
_exptl_crystal_density_diffrn 1.556
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 1384
_exptl_absorpt_coefficient_mu 0.880
# Sheldrick geometric approximatio 0.90 0.92
# No experimental values of Tmin/max available
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min 0.90
_exptl_absorpt_correction_T_max 0.92
_diffrn_measurement_device 'Bruker Kappa Apex2'
_diffrn_measurement_device_type 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 123
_diffrn_reflns_number 79592
_reflns_number_total 7731
_diffrn_reflns_av_R_equivalents 0.040
# Number of reflections with Friedels Law is 7731
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 7758
_diffrn_reflns_theta_min 2.104
_diffrn_reflns_theta_max 37.750
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 37.750
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min -26
_diffrn_reflns_limit_h_max 26
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_l_min -26
_diffrn_reflns_limit_l_max 26
_reflns_limit_h_min -26
_reflns_limit_h_max 26
_reflns_limit_k_min 0
_reflns_limit_k_max 21
_reflns_limit_l_min 0
_reflns_limit_l_max 26
_oxford_diffrn_Wilson_B_factor 1.22
_oxford_diffrn_Wilson_scale 204.32
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.72
_refine_diff_density_max 0.65
# 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 6961
_refine_ls_number_restraints 0
_refine_ls_number_parameters 200
_oxford_refine_ls_R_factor_ref 0.0304
_refine_ls_wR_factor_ref 0.0327
_refine_ls_goodness_of_fit_ref 1.0580
_refine_ls_shift/su_max 0.001295
# The values computed from all data
_oxford_reflns_number_all 7722
_refine_ls_R_factor_all 0.0345
_refine_ls_wR_factor_all 0.0466
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 7325
_refine_ls_R_factor_gt 0.0319
_refine_ls_wR_factor_gt 0.0339
# 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:
0.134 0.114 0.366E-01
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.
Watkin D.J. (1994).
Acta Cryst, A50, 411-437.
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
Bruker Analytical X-ray Systems, Inc., 2006. Apex2,
Version 2 User Manual, M86-E01078, Madison, WI.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
Cu1 Cu 0.5000 0.119920(10) 0.7500 0.0149 1.0000 Uani S T . . . . .
N1 N 0.55974(4) 0.05856(5) 0.65822(4) 0.0150 1.0000 Uani . . . . . . .
N2 N 0.45175(4) 0.22422(5) 0.64481(4) 0.0145 1.0000 Uani . . . . . . .
N3 N 0.30102(4) 0.24440(5) 0.74327(5) 0.0191 1.0000 Uani . . . . . . .
C1 C 0.60754(5) -0.03150(6) 0.66579(5) 0.0185 1.0000 Uani . . . . . . .
C2 C 0.65021(5) -0.06562(7) 0.59944(6) 0.0224 1.0000 Uani . . . . . . .
C3 C 0.64269(6) -0.00435(7) 0.52216(6) 0.0237 1.0000 Uani . . . . . . .
C4 C 0.59265(5) 0.08830(7) 0.51297(5) 0.0203 1.0000 Uani . . . . . . .
C5 C 0.55161(4) 0.11774(5) 0.58241(4) 0.0150 1.0000 Uani . . . . . . .
C6 C 0.49629(4) 0.21468(5) 0.57829(4) 0.0151 1.0000 Uani . . . . . . .
C7 C 0.49160(5) 0.29156(6) 0.51123(5) 0.0199 1.0000 Uani . . . . . . .
C8 C 0.43960(6) 0.38116(6) 0.51344(5) 0.0220 1.0000 Uani . . . . . . .
C9 C 0.39475(5) 0.39221(6) 0.58259(5) 0.0202 1.0000 Uani . . . . . . .
C10 C 0.40193(4) 0.31175(5) 0.64766(5) 0.0161 1.0000 Uani . . . . . . .
C11 C 0.35656(5) 0.32165(6) 0.72265(5) 0.0169 1.0000 Uani . . . . . . .
C12 C 0.36106(5) 0.40375(6) 0.78417(6) 0.0214 1.0000 Uani . . . . . . .
C13 C 0.30670(6) 0.37482(7) 0.84412(6) 0.0246 1.0000 Uani . . . . . . .
C14 C 0.27008(5) 0.27725(7) 0.81671(6) 0.0230 1.0000 Uani . . . . . . .
C15 C 0.26911(5) 0.15116(7) 0.68898(6) 0.0239 1.0000 Uani . . . . . . .
P1 P 0.5000 0.70157(2) 0.7500 0.0187 1.0000 Uani S T . . . . .
F1 F 0.45061(10) 0.61322(8) 0.68266(6) 0.0693 1.0000 Uani . . . . . . .
F2 F 0.57771(4) 0.70339(8) 0.69667(4) 0.0454 1.0000 Uani . . . . . . .
F3 F 0.45075(5) 0.79188(6) 0.68360(4) 0.0346 1.0000 Uani . . . . . . .
H11 H 0.6115 -0.0718 0.7195 0.0230 1.0000 Uiso R . . . . . .
H21 H 0.6839 -0.1295 0.6083 0.0286 1.0000 Uiso R . . . . . .
H31 H 0.6709 -0.0253 0.4751 0.0302 1.0000 Uiso R . . . . . .
H41 H 0.5867 0.1300 0.4600 0.0269 1.0000 Uiso R . . . . . .
H71 H 0.5231 0.2835 0.4654 0.0250 1.0000 Uiso R . . . . . .
H81 H 0.4352 0.4339 0.4682 0.0271 1.0000 Uiso R . . . . . .
H91 H 0.3597 0.4515 0.5857 0.0247 1.0000 Uiso R . . . . . .
H121 H 0.3954 0.4666 0.7859 0.0275 1.0000 Uiso R . . . . . .
H131 H 0.2974 0.4141 0.8942 0.0307 1.0000 Uiso R . . . . . .
H141 H 0.2299 0.2374 0.8406 0.0294 1.0000 Uiso R . . . . . .
H152 H 0.2356 0.1085 0.7201 0.0372 1.0000 Uiso R . . . . . .
H151 H 0.3179 0.1087 0.6783 0.0348 1.0000 Uiso R . . . . . .
H153 H 0.2322 0.1741 0.6328 0.0365 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
Cu1 0.01609(5) 0.01672(5) 0.01243(5) 0.0000 0.00411(3) 0.0000
N1 0.0155(2) 0.0149(2) 0.0148(2) 0.00008(16) 0.00379(16) 0.00059(17)
N2 0.0144(2) 0.0144(2) 0.0143(2) 0.00032(16) 0.00228(16) 0.00071(16)
N3 0.0157(2) 0.0176(2) 0.0245(3) -0.0015(2) 0.00521(19) 0.00029(18)
C1 0.0185(3) 0.0170(3) 0.0202(3) 0.0003(2) 0.0045(2) 0.0027(2)
C2 0.0205(3) 0.0221(3) 0.0256(3) -0.0030(2) 0.0069(2) 0.0050(2)
C3 0.0230(3) 0.0274(3) 0.0229(3) -0.0041(3) 0.0099(2) 0.0032(3)
C4 0.0220(3) 0.0241(3) 0.0164(2) -0.0008(2) 0.0077(2) 0.0012(2)
C5 0.0156(2) 0.0161(2) 0.0133(2) -0.00051(18) 0.00335(18) -0.00061(19)
C6 0.0160(2) 0.0153(2) 0.0135(2) 0.00054(18) 0.00233(18) -0.00056(19)
C7 0.0242(3) 0.0196(3) 0.0158(2) 0.0033(2) 0.0043(2) -0.0006(2)
C8 0.0262(3) 0.0185(3) 0.0200(3) 0.0049(2) 0.0021(2) -0.0006(2)
C9 0.0221(3) 0.0152(3) 0.0221(3) 0.0028(2) 0.0018(2) 0.0019(2)
C10 0.0154(2) 0.0142(2) 0.0178(2) -0.00022(19) 0.00171(19) 0.00060(19)
C11 0.0153(2) 0.0147(2) 0.0204(3) -0.0009(2) 0.0032(2) 0.00184(19)
C12 0.0217(3) 0.0175(3) 0.0250(3) -0.0041(2) 0.0051(2) 0.0021(2)
C13 0.0236(3) 0.0264(3) 0.0248(3) -0.0047(3) 0.0072(3) 0.0046(3)
C14 0.0189(3) 0.0255(3) 0.0262(3) 0.0004(3) 0.0082(2) 0.0033(2)
C15 0.0173(3) 0.0196(3) 0.0340(4) -0.0046(3) 0.0039(3) -0.0020(2)
P1 0.02364(12) 0.01748(11) 0.01463(9) 0.0000 0.00333(8) 0.0000
F1 0.1299(10) 0.0463(5) 0.0293(3) -0.0125(3) 0.0117(5) -0.0530(6)
F2 0.0278(3) 0.0876(6) 0.0225(2) -0.0074(3) 0.0090(2) 0.0207(3)
F3 0.0398(3) 0.0442(4) 0.0219(2) 0.0120(2) 0.0113(2) 0.0203(3)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.07413(6)
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
Cu1 . N2 5_656 2.0758(6) yes
Cu1 . N1 5_656 1.9918(6) yes
Cu1 . N1 . 1.9918(6) yes
Cu1 . N2 . 2.0758(6) yes
N1 . C1 . 1.3445(9) yes
N1 . C5 . 1.3529(9) yes
N2 . C6 . 1.3497(9) yes
N2 . C10 . 1.3511(9) yes
N3 . C11 . 1.3800(10) yes
N3 . C14 . 1.3713(11) yes
N3 . C15 . 1.4554(11) yes
C1 . C2 . 1.3899(11) yes
C1 . H11 . 0.951 no
C2 . C3 . 1.3869(12) yes
C2 . H21 . 0.952 no
C3 . C4 . 1.3899(12) yes
C3 . H31 . 0.954 no
C4 . C5 . 1.3968(10) yes
C4 . H41 . 0.948 no
C5 . C6 . 1.4844(10) yes
C6 . C7 . 1.3936(10) yes
C7 . C8 . 1.3906(12) yes
C7 . H71 . 0.939 no
C8 . C9 . 1.3890(12) yes
C8 . H81 . 0.946 no
C9 . C10 . 1.4006(10) yes
C9 . H91 . 0.930 no
C10 . C11 . 1.4705(10) yes
C11 . C12 . 1.3826(10) yes
C12 . C13 . 1.4190(12) yes
C12 . H121 . 0.950 no
C13 . C14 . 1.3766(13) yes
C13 . H131 . 0.944 no
C14 . H141 . 0.934 no
C15 . H152 . 0.944 no
C15 . H151 . 0.970 no
C15 . H153 . 0.963 no
P1 . F3 5_656 1.5981(6) yes
P1 . F2 5_656 1.5961(6) yes
P1 . F1 5_656 1.5891(7) yes
P1 . F1 . 1.5891(7) yes
P1 . F2 . 1.5961(6) yes
P1 . F3 . 1.5981(6) 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
N2 5_656 Cu1 . N1 5_656 81.43(2) yes
N2 5_656 Cu1 . N1 . 129.55(2) yes
N1 5_656 Cu1 . N1 . 134.50(4) yes
N2 5_656 Cu1 . N2 . 101.79(3) yes
N1 5_656 Cu1 . N2 . 129.55(2) yes
N1 . Cu1 . N2 . 81.43(2) yes
Cu1 . N1 . C1 . 126.83(5) yes
Cu1 . N1 . C5 . 114.33(5) yes
C1 . N1 . C5 . 118.81(6) yes
Cu1 . N2 . C6 . 111.19(4) yes
Cu1 . N2 . C10 . 127.04(5) yes
C6 . N2 . C10 . 119.23(6) yes
C11 . N3 . C14 . 108.77(7) yes
C11 . N3 . C15 . 126.15(7) yes
C14 . N3 . C15 . 124.45(7) yes
N1 . C1 . C2 . 122.69(7) yes
N1 . C1 . H11 . 116.9 no
C2 . C1 . H11 . 120.4 no
C1 . C2 . C3 . 118.51(7) yes
C1 . C2 . H21 . 119.6 no
C3 . C2 . H21 . 121.9 no
C2 . C3 . C4 . 119.41(7) yes
C2 . C3 . H31 . 120.9 no
C4 . C3 . H31 . 119.7 no
C3 . C4 . C5 . 118.96(7) yes
C3 . C4 . H41 . 119.8 no
C5 . C4 . H41 . 121.3 no
C4 . C5 . N1 . 121.61(7) yes
C4 . C5 . C6 . 122.80(6) yes
N1 . C5 . C6 . 115.59(6) yes
C5 . C6 . N2 . 115.42(6) yes
C5 . C6 . C7 . 122.42(6) yes
N2 . C6 . C7 . 122.16(6) yes
C6 . C7 . C8 . 118.72(7) yes
C6 . C7 . H71 . 120.9 no
C8 . C7 . H71 . 120.4 no
C7 . C8 . C9 . 119.36(7) yes
C7 . C8 . H81 . 119.9 no
C9 . C8 . H81 . 120.8 no
C8 . C9 . C10 . 119.06(7) yes
C8 . C9 . H91 . 121.0 no
C10 . C9 . H91 . 119.9 no
C9 . C10 . N2 . 121.46(7) yes
C9 . C10 . C11 . 120.52(6) yes
N2 . C10 . C11 . 118.01(6) yes
C10 . C11 . N3 . 123.15(6) yes
C10 . C11 . C12 . 128.63(7) yes
N3 . C11 . C12 . 108.20(7) yes
C11 . C12 . C13 . 107.07(7) yes
C11 . C12 . H121 . 125.7 no
C13 . C12 . H121 . 127.3 no
C12 . C13 . C14 . 107.41(7) yes
C12 . C13 . H131 . 127.0 no
C14 . C13 . H131 . 125.6 no
C13 . C14 . N3 . 108.54(7) yes
C13 . C14 . H141 . 128.9 no
N3 . C14 . H141 . 122.6 no
N3 . C15 . H152 . 109.3 no
N3 . C15 . H151 . 110.7 no
H152 . C15 . H151 . 108.1 no
N3 . C15 . H153 . 109.0 no
H152 . C15 . H153 . 109.0 no
H151 . C15 . H153 . 110.7 no
F3 5_656 P1 . F2 5_656 88.97(4) yes
F3 5_656 P1 . F1 5_656 89.44(5) yes
F2 5_656 P1 . F1 5_656 89.85(6) yes
F3 5_656 P1 . F1 . 179.04(5) yes
F2 5_656 P1 . F1 . 91.29(6) yes
F1 5_656 P1 . F1 . 91.48(9) yes
F3 5_656 P1 . F2 . 89.86(4) yes
F2 5_656 P1 . F2 . 178.36(8) yes
F1 5_656 P1 . F2 . 91.29(6) yes
F1 . P1 . F2 . 89.85(6) yes
F3 5_656 P1 . F3 . 89.63(6) yes
F2 5_656 P1 . F3 . 89.86(4) yes
F1 5_656 P1 . F3 . 179.04(5) yes
F1 . P1 . F3 . 89.45(5) yes
F2 . P1 . F3 . 88.97(4) yes
# Attachment '- pk65.cif'
data_pk65
_database_code_depnum_ccdc_archive 'CCDC 828951'
#TrackingRef '- pk65.cif'
_publ_section_exptl_refinement
# Some potentially useful phrases are donated by Bill Clegg:
;
In the absence of significant anomalous scattering, Friedel pairs were
merged.
The absolute configuration was arbitrarily assigned.
The relatively large ratio of minimum to maximum corrections applied
in the multiscan process (1:nnn) reflect changes in the illuminated
volume of the crystal.
Changes in illuminated volume were kept to a minimum, and were
taken into account (G\"orbitz, 1999) by the multi-scan inter-frame
scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997).
G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098.
The H atoms were all located in a difference map, but those
attached to carbon atoms were repositioned geometrically.
The H atoms were initially refined with soft restraints on the
bond lengths and angles to regularise their geometry
(C---H in the range 0.93--0.98,
N---H in the range 0.86--0.89
N---H to 0.86
O---H = 0.82
\%A)
and
U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom),
after which the positions were refined with riding constraints.
;
_publ_section_exptl_prep
# Brief details or a reference. Include solvent if known
;
?
;
# Hand-made tables can be put in the cif. The number of columns
# is set in the loop header.
# The contants of each column can either be a piece of text
# without any spaces (eg a number) or other text enclosed in " "
# Remove the leading # in the following example
#geom_extra_table_head_A
#;
#Table 2.
#Molecular parameters deviating most from MOGUL averages
#;
#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
#_geom_extra_tableA_col_4
#
#Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d"
#N5-C6-C4 129 124 "7 (\%)"
#C3-O10-C2 105 109 "2 (\%)"
#C6-O7 1.25 1.22 ".02 (\%A)"
#
# End of 'script/refcif-b.dat'
#end of refcif
_cell_length_a 8.9873(7)
_cell_length_b 10.3479(7)
_cell_length_c 12.9086(10)
_cell_angle_alpha 98.400(4)
_cell_angle_beta 99.933(4)
_cell_angle_gamma 90.639(4)
_cell_volume 1169.00(15)
_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'
_cell_formula_units_Z 4
# Given Formula = C15 H13 N3
# Dc = 1.34 Fooo = 496.00 Mu = 0.82 M = 470.58
# Found Formula = C15 H13 N3
# Dc = 1.34 FOOO = 496.00 Mu = 0.82 M = 470.58
_chemical_formula_sum 'C15 H13 N3'
_chemical_formula_moiety 'C15 H13 N3'
_chemical_compound_source ?
_chemical_formula_weight 235.29
_cell_measurement_reflns_used 9964
_cell_measurement_theta_min 4
_cell_measurement_theta_max 32
_cell_measurement_temperature 123
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.09
_exptl_crystal_size_mid 0.17
_exptl_crystal_size_max 0.34
_exptl_crystal_density_diffrn 1.337
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 496
_exptl_absorpt_coefficient_mu 0.082
# Sheldrick geometric approximatio 0.99 0.99
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min 0.99
_exptl_absorpt_correction_T_max 0.99
_diffrn_measurement_device 'Bruker Kappa Apex2'
_diffrn_measurement_device_type 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 123
_diffrn_reflns_number 32162
_reflns_number_total 7705
_diffrn_reflns_av_R_equivalents 0.033
# Number of reflections with Friedels Law is 7705
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 7852
_diffrn_reflns_theta_min 1.991
_diffrn_reflns_theta_max 31.605
_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full 27.496
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 19
_reflns_limit_h_min -13
_reflns_limit_h_max 13
_reflns_limit_k_min -15
_reflns_limit_k_max 15
_reflns_limit_l_min 0
_reflns_limit_l_max 19
_oxford_diffrn_Wilson_B_factor 1.66
_oxford_diffrn_Wilson_scale 38.26
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.41
_refine_diff_density_max 0.70
# 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 6116
_refine_ls_number_restraints 0
_refine_ls_number_parameters 325
_oxford_refine_ls_R_factor_ref 0.0785
_refine_ls_wR_factor_ref 0.0748
_refine_ls_goodness_of_fit_ref 0.9314
_refine_ls_shift/su_max 0.000357
# The values computed from all data
_oxford_reflns_number_all 7687
_refine_ls_R_factor_all 0.0923
_refine_ls_wR_factor_all 0.1079
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 6837
_refine_ls_R_factor_gt 0.0832
_refine_ls_wR_factor_gt 0.0787
# 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:
0.379 0.392 0.134
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.
Watkin D.J. (1994).
Acta Cryst, A50, 411-437.
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
Bruker Analytical X-ray Systems, Inc., 2006. Apex2,
Version 2 User Manual, M86-E01078, Madison, WI.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
N1 N 0.79286(17) 0.48105(14) 0.53926(12) 0.0246 1.0000 Uani . . . . . . .
N2 N 0.67638(15) 0.14586(13) 0.43729(10) 0.0183 1.0000 Uani . . . . . . .
N3 N 0.64688(15) -0.13504(13) 0.43752(11) 0.0199 1.0000 Uani . . . . . . .
C1 C 0.9029(2) 0.54882(17) 0.60999(14) 0.0277 1.0000 Uani . . . . . . .
C2 C 1.0256(2) 0.49368(17) 0.66487(14) 0.0263 1.0000 Uani . . . . . . .
C3 C 1.03515(19) 0.35826(17) 0.64634(14) 0.0241 1.0000 Uani . . . . . . .
C4 C 0.92160(18) 0.28557(16) 0.57397(13) 0.0220 1.0000 Uani . . . . . . .
C5 C 0.80285(18) 0.35013(15) 0.52106(12) 0.0193 1.0000 Uani . . . . . . .
C6 C 0.68225(17) 0.27638(15) 0.44010(12) 0.0189 1.0000 Uani . . . . . . .
C7 C 0.5834(2) 0.34006(17) 0.37063(14) 0.0261 1.0000 Uani . . . . . . .
C8 C 0.4745(2) 0.26516(18) 0.29609(15) 0.0297 1.0000 Uani . . . . . . .
C9 C 0.4651(2) 0.13154(17) 0.29391(14) 0.0255 1.0000 Uani . . . . . . .
C10 C 0.56821(17) 0.07400(15) 0.36732(12) 0.0183 1.0000 Uani . . . . . . .
C11 C 0.55648(17) -0.06695(15) 0.36733(12) 0.0184 1.0000 Uani . . . . . . .
C12 C 0.45338(19) -0.15756(16) 0.30131(13) 0.0228 1.0000 Uani . . . . . . .
C13 C 0.4821(2) -0.28126(17) 0.33181(14) 0.0256 1.0000 Uani . . . . . . .
C14 C 0.60132(19) -0.26456(16) 0.41587(14) 0.0241 1.0000 Uani . . . . . . .
C15 C 0.76860(19) -0.08480(16) 0.52493(13) 0.0238 1.0000 Uani . . . . . . .
N4 N 0.88668(16) 1.03713(14) 0.85593(12) 0.0232 1.0000 Uani . . . . . . .
N5 N 0.80842(15) 0.73910(13) 0.95437(10) 0.0188 1.0000 Uani . . . . . . .
N6 N 0.78289(16) 0.45866(14) 0.96211(11) 0.0230 1.0000 Uani . . . . . . .
C16 C 0.9697(2) 1.07891(17) 0.78979(14) 0.0266 1.0000 Uani . . . . . . .
C17 C 1.0657(2) 1.00122(18) 0.73681(13) 0.0257 1.0000 Uani . . . . . . .
C18 C 1.0770(2) 0.87191(17) 0.75346(14) 0.0260 1.0000 Uani . . . . . . .
C19 C 0.99247(19) 0.82648(16) 0.82220(13) 0.0222 1.0000 Uani . . . . . . .
C20 C 0.89860(17) 0.91163(14) 0.87198(12) 0.0178 1.0000 Uani . . . . . . .
C21 C 0.80575(17) 0.86762(15) 0.94644(12) 0.0184 1.0000 Uani . . . . . . .
C22 C 0.72261(18) 0.95539(16) 1.00283(13) 0.0223 1.0000 Uani . . . . . . .
C23 C 0.63915(19) 0.90862(17) 1.07213(14) 0.0254 1.0000 Uani . . . . . . .
C24 C 0.64042(19) 0.77715(17) 1.08093(14) 0.0252 1.0000 Uani . . . . . . .
C25 C 0.72657(17) 0.69385(15) 1.02018(12) 0.0196 1.0000 Uani . . . . . . .
C26 C 0.72644(18) 0.55499(16) 1.02908(13) 0.0207 1.0000 Uani . . . . . . .
C27 C 0.6701(2) 0.49383(18) 1.10407(14) 0.0265 1.0000 Uani . . . . . . .
C28 C 0.6928(2) 0.35875(18) 1.08151(15) 0.0303 1.0000 Uani . . . . . . .
C29 C 0.7621(2) 0.33951(17) 0.99397(15) 0.0289 1.0000 Uani . . . . . . .
C30 C 0.8533(2) 0.47113(17) 0.87037(15) 0.0282 1.0000 Uani . . . . . . .
H11 H 0.8958 0.6411 0.6214 0.0355 1.0000 Uiso R . . . . . .
H21 H 1.1003 0.5447 0.7139 0.0356 1.0000 Uiso R . . . . . .
H31 H 1.1175 0.3188 0.6843 0.0341 1.0000 Uiso R . . . . . .
H41 H 0.9239 0.1922 0.5619 0.0288 1.0000 Uiso R . . . . . .
H71 H 0.5887 0.4319 0.3757 0.0323 1.0000 Uiso R . . . . . .
H81 H 0.4101 0.3081 0.2469 0.0381 1.0000 Uiso R . . . . . .
H91 H 0.3912 0.0780 0.2443 0.0346 1.0000 Uiso R . . . . . .
H121 H 0.3783 -0.1397 0.2463 0.0297 1.0000 Uiso R . . . . . .
H131 H 0.4340 -0.3628 0.3011 0.0339 1.0000 Uiso R . . . . . .
H141 H 0.6485 -0.3328 0.4515 0.0325 1.0000 Uiso R . . . . . .
H152 H 0.8053 -0.1592 0.5600 0.0398 1.0000 Uiso R . . . . . .
H151 H 0.7274 -0.0196 0.5731 0.0397 1.0000 Uiso R . . . . . .
H153 H 0.8493 -0.0435 0.4992 0.0402 1.0000 Uiso R . . . . . .
H161 H 0.9613 1.1655 0.7784 0.0344 1.0000 Uiso R . . . . . .
H171 H 1.1214 1.0367 0.6918 0.0331 1.0000 Uiso R . . . . . .
H181 H 1.1407 0.8143 0.7186 0.0360 1.0000 Uiso R . . . . . .
H191 H 0.9945 0.7365 0.8313 0.0292 1.0000 Uiso R . . . . . .
H221 H 0.7243 1.0462 0.9963 0.0255 1.0000 Uiso R . . . . . .
H231 H 0.5836 0.9650 1.1140 0.0330 1.0000 Uiso R . . . . . .
H241 H 0.5832 0.7416 1.1276 0.0348 1.0000 Uiso R . . . . . .
H271 H 0.6236 0.5380 1.1588 0.0351 1.0000 Uiso R . . . . . .
H281 H 0.6644 0.2884 1.1174 0.0380 1.0000 Uiso R . . . . . .
H291 H 0.7915 0.2561 0.9598 0.0352 1.0000 Uiso R . . . . . .
H302 H 0.8764 0.3847 0.8358 0.0476 1.0000 Uiso R . . . . . .
H301 H 0.7878 0.5150 0.8195 0.0480 1.0000 Uiso R . . . . . .
H303 H 0.9485 0.5217 0.8905 0.0485 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 0.0311(7) 0.0171(6) 0.0246(7) 0.0030(5) 0.0029(6) 0.0016(5)
N2 0.0192(6) 0.0186(6) 0.0184(6) 0.0041(5) 0.0054(5) 0.0025(5)
N3 0.0198(6) 0.0173(6) 0.0220(6) 0.0017(5) 0.0032(5) 0.0030(5)
C1 0.0380(9) 0.0176(7) 0.0261(8) 0.0014(6) 0.0040(7) -0.0014(6)
C2 0.0305(8) 0.0242(8) 0.0239(7) 0.0030(6) 0.0048(6) -0.0043(6)
C3 0.0221(7) 0.0261(8) 0.0251(7) 0.0064(6) 0.0044(6) 0.0000(6)
C4 0.0233(7) 0.0181(7) 0.0250(7) 0.0045(6) 0.0045(6) -0.0001(5)
C5 0.0224(7) 0.0167(6) 0.0201(7) 0.0046(5) 0.0060(5) 0.0006(5)
C6 0.0207(7) 0.0193(7) 0.0181(6) 0.0044(5) 0.0063(5) 0.0029(5)
C7 0.0314(8) 0.0210(7) 0.0260(8) 0.0083(6) 0.0014(6) 0.0033(6)
C8 0.0307(9) 0.0280(8) 0.0291(8) 0.0097(7) -0.0029(7) 0.0055(7)
C9 0.0250(8) 0.0261(8) 0.0237(7) 0.0057(6) -0.0021(6) 0.0016(6)
C10 0.0187(6) 0.0184(6) 0.0192(6) 0.0035(5) 0.0064(5) 0.0029(5)
C11 0.0178(6) 0.0195(6) 0.0185(6) 0.0027(5) 0.0050(5) 0.0029(5)
C12 0.0220(7) 0.0242(7) 0.0215(7) 0.0005(6) 0.0044(6) 0.0011(6)
C13 0.0255(8) 0.0208(7) 0.0305(8) -0.0013(6) 0.0092(6) -0.0016(6)
C14 0.0263(8) 0.0177(7) 0.0303(8) 0.0032(6) 0.0105(6) 0.0037(6)
C15 0.0230(7) 0.0211(7) 0.0262(8) 0.0056(6) -0.0009(6) 0.0016(6)
N4 0.0244(6) 0.0197(6) 0.0276(7) 0.0086(5) 0.0061(5) 0.0030(5)
N5 0.0189(6) 0.0177(6) 0.0198(6) 0.0035(5) 0.0032(5) 0.0003(5)
N6 0.0264(7) 0.0182(6) 0.0245(6) 0.0040(5) 0.0041(5) -0.0001(5)
C16 0.0290(8) 0.0222(7) 0.0313(8) 0.0118(7) 0.0065(7) 0.0014(6)
C17 0.0263(8) 0.0300(8) 0.0228(7) 0.0095(6) 0.0052(6) -0.0021(6)
C18 0.0284(8) 0.0262(8) 0.0254(8) 0.0031(6) 0.0112(6) 0.0014(6)
C19 0.0249(7) 0.0186(7) 0.0238(7) 0.0026(6) 0.0070(6) -0.0003(6)
C20 0.0190(6) 0.0163(6) 0.0174(6) 0.0025(5) 0.0013(5) 0.0002(5)
C21 0.0177(6) 0.0184(6) 0.0185(6) 0.0035(5) 0.0007(5) 0.0010(5)
C22 0.0229(7) 0.0199(7) 0.0237(7) 0.0022(6) 0.0040(6) 0.0034(6)
C23 0.0247(8) 0.0246(8) 0.0285(8) 0.0017(6) 0.0107(6) 0.0049(6)
C24 0.0251(8) 0.0255(8) 0.0269(8) 0.0041(6) 0.0095(6) 0.0018(6)
C25 0.0180(6) 0.0203(7) 0.0200(7) 0.0039(5) 0.0011(5) -0.0014(5)
C26 0.0199(7) 0.0203(7) 0.0220(7) 0.0040(6) 0.0032(5) -0.0010(5)
C27 0.0252(8) 0.0285(8) 0.0282(8) 0.0092(7) 0.0071(6) -0.0008(6)
C28 0.0340(9) 0.0253(8) 0.0333(9) 0.0123(7) 0.0044(7) -0.0042(7)
C29 0.0354(9) 0.0184(7) 0.0317(9) 0.0054(6) 0.0014(7) -0.0022(6)
C30 0.0384(9) 0.0195(7) 0.0286(8) 0.0020(6) 0.0127(7) -0.0001(7)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.1697(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C1 . 1.338(2) yes
N1 . C5 . 1.347(2) yes
N2 . C6 . 1.3460(19) yes
N2 . C10 . 1.341(2) yes
N3 . C11 . 1.3866(19) yes
N3 . C14 . 1.372(2) yes
N3 . C15 . 1.460(2) yes
C1 . C2 . 1.381(3) yes
C1 . H11 . 0.949 no
C2 . C3 . 1.393(2) yes
C2 . H21 . 0.937 no
C3 . C4 . 1.389(2) yes
C3 . H31 . 0.946 no
C4 . C5 . 1.396(2) yes
C4 . H41 . 0.957 no
C5 . C6 . 1.486(2) yes
C6 . C7 . 1.392(2) yes
C7 . C8 . 1.387(3) yes
C7 . H71 . 0.943 no
C8 . C9 . 1.380(2) yes
C8 . H81 . 0.947 no
C9 . C10 . 1.409(2) yes
C9 . H91 . 0.949 no
C10 . C11 . 1.461(2) yes
C11 . C12 . 1.392(2) yes
C12 . C13 . 1.407(2) yes
C12 . H121 . 0.933 no
C13 . C14 . 1.376(3) yes
C13 . H131 . 0.944 no
C14 . H141 . 0.962 no
C15 . H152 . 0.981 no
C15 . H151 . 0.971 no
C15 . H153 . 0.968 no
N4 . C16 . 1.339(2) yes
N4 . C20 . 1.3472(19) yes
N5 . C21 . 1.3489(19) yes
N5 . C25 . 1.3439(19) yes
N6 . C26 . 1.382(2) yes
N6 . C29 . 1.376(2) yes
N6 . C30 . 1.456(2) yes
C16 . C17 . 1.385(3) yes
C16 . H161 . 0.931 no
C17 . C18 . 1.388(2) yes
C17 . H171 . 0.939 no
C18 . C19 . 1.390(2) yes
C18 . H181 . 0.951 no
C19 . C20 . 1.393(2) yes
C19 . H191 . 0.956 no
C20 . C21 . 1.491(2) yes
C21 . C22 . 1.387(2) yes
C22 . C23 . 1.395(2) yes
C22 . H221 . 0.956 no
C23 . C24 . 1.382(2) yes
C23 . H231 . 0.943 no
C24 . C25 . 1.409(2) yes
C24 . H241 . 0.965 no
C25 . C26 . 1.458(2) yes
C26 . C27 . 1.391(2) yes
C27 . C28 . 1.410(3) yes
C27 . H271 . 0.945 no
C28 . C29 . 1.373(3) yes
C28 . H281 . 0.972 no
C29 . H291 . 0.971 no
C30 . H302 . 0.980 no
C30 . H301 . 0.972 no
C30 . H303 . 0.973 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . N1 . C5 . 117.45(15) yes
C6 . N2 . C10 . 119.07(13) yes
C11 . N3 . C14 . 109.00(13) yes
C11 . N3 . C15 . 128.76(13) yes
C14 . N3 . C15 . 122.20(14) yes
N1 . C1 . C2 . 124.42(16) yes
N1 . C1 . H11 . 116.8 no
C2 . C1 . H11 . 118.7 no
C1 . C2 . C3 . 118.00(16) yes
C1 . C2 . H21 . 121.8 no
C3 . C2 . H21 . 120.2 no
C2 . C3 . C4 . 118.70(16) yes
C2 . C3 . H31 . 119.0 no
C4 . C3 . H31 . 122.2 no
C3 . C4 . C5 . 119.24(15) yes
C3 . C4 . H41 . 120.1 no
C5 . C4 . H41 . 120.6 no
C4 . C5 . N1 . 122.19(15) yes
C4 . C5 . C6 . 120.90(14) yes
N1 . C5 . C6 . 116.90(14) yes
C5 . C6 . N2 . 116.19(13) yes
C5 . C6 . C7 . 121.16(14) yes
N2 . C6 . C7 . 122.64(15) yes
C6 . C7 . C8 . 118.22(15) yes
C6 . C7 . H71 . 120.7 no
C8 . C7 . H71 . 121.1 no
C7 . C8 . C9 . 119.72(15) yes
C7 . C8 . H81 . 118.2 no
C9 . C8 . H81 . 122.1 no
C8 . C9 . C10 . 118.88(16) yes
C8 . C9 . H91 . 121.5 no
C10 . C9 . H91 . 119.6 no
C9 . C10 . N2 . 121.42(14) yes
C9 . C10 . C11 . 119.19(14) yes
N2 . C10 . C11 . 119.39(13) yes
C10 . C11 . N3 . 125.06(14) yes
C10 . C11 . C12 . 127.98(14) yes
N3 . C11 . C12 . 106.94(13) yes
C11 . C12 . C13 . 108.15(15) yes
C11 . C12 . H121 . 126.1 no
C13 . C12 . H121 . 125.8 no
C12 . C13 . C14 . 107.10(15) yes
C12 . C13 . H131 . 128.7 no
C14 . C13 . H131 . 124.2 no
C13 . C14 . N3 . 108.82(15) yes
C13 . C14 . H141 . 125.9 no
N3 . C14 . H141 . 125.2 no
N3 . C15 . H152 . 107.1 no
N3 . C15 . H151 . 108.0 no
H152 . C15 . H151 . 111.4 no
N3 . C15 . H153 . 111.0 no
H152 . C15 . H153 . 110.9 no
H151 . C15 . H153 . 108.4 no
C16 . N4 . C20 . 117.54(15) yes
C21 . N5 . C25 . 118.42(14) yes
C26 . N6 . C29 . 109.15(14) yes
C26 . N6 . C30 . 128.93(14) yes
C29 . N6 . C30 . 121.92(15) yes
N4 . C16 . C17 . 124.15(15) yes
N4 . C16 . H161 . 117.6 no
C17 . C16 . H161 . 118.2 no
C16 . C17 . C18 . 117.98(15) yes
C16 . C17 . H171 . 119.9 no
C18 . C17 . H171 . 122.1 no
C17 . C18 . C19 . 118.90(16) yes
C17 . C18 . H181 . 121.3 no
C19 . C18 . H181 . 119.8 no
C18 . C19 . C20 . 119.17(15) yes
C18 . C19 . H191 . 119.9 no
C20 . C19 . H191 . 120.8 no
C19 . C20 . N4 . 122.26(14) yes
C19 . C20 . C21 . 121.20(13) yes
N4 . C20 . C21 . 116.54(14) yes
C20 . C21 . N5 . 115.82(13) yes
C20 . C21 . C22 . 120.97(14) yes
N5 . C21 . C22 . 123.21(14) yes
C21 . C22 . C23 . 118.32(15) yes
C21 . C22 . H221 . 121.2 no
C23 . C22 . H221 . 120.5 no
C22 . C23 . C24 . 119.15(15) yes
C22 . C23 . H231 . 121.5 no
C24 . C23 . H231 . 119.4 no
C23 . C24 . C25 . 119.19(15) yes
C23 . C24 . H241 . 121.2 no
C25 . C24 . H241 . 119.6 no
C24 . C25 . N5 . 121.70(14) yes
C24 . C25 . C26 . 118.96(14) yes
N5 . C25 . C26 . 119.34(14) yes
C25 . C26 . N6 . 125.35(14) yes
C25 . C26 . C27 . 127.58(15) yes
N6 . C26 . C27 . 107.07(14) yes
C26 . C27 . C28 . 107.93(16) yes
C26 . C27 . H271 . 124.1 no
C28 . C27 . H271 . 127.9 no
C27 . C28 . C29 . 107.33(15) yes
C27 . C28 . H281 . 129.0 no
C29 . C28 . H281 . 123.6 no
N6 . C29 . C28 . 108.51(16) yes
N6 . C29 . H291 . 125.4 no
C28 . C29 . H291 . 126.1 no
N6 . C30 . H302 . 110.3 no
N6 . C30 . H301 . 110.8 no
H302 . C30 . H301 . 109.6 no
N6 . C30 . H303 . 111.9 no
H302 . C30 . H303 . 106.8 no
H301 . C30 . H303 . 107.3 no