# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
#
data_I
_audit_creation_date 2013-05-28T22:13:43-00:00
_audit_creation_method 'WinGX routine CIF_UPDATE'
#==============================================================================
# CHEMICAL DATA
_chemical_name_systematic ?
_chemical_formula_moiety 'C45 H48 N6 O6, C1 H1 Cl3'
_chemical_formula_sum 'C46 H49 Cl3 N6 O6'
_chemical_formula_weight 888.26
#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system triclinic
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
_symmetry_Int_Tables_number 2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 12.2119(3)
_cell_length_b 14.9841(3)
_cell_length_c 15.3037(3)
_cell_angle_alpha 63.9270(10)
_cell_angle_beta 73.1140(10)
_cell_angle_gamma 69.0890(10)
_cell_volume 2319.72(9)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 9254
_cell_measurement_theta_min 2.528
_cell_measurement_theta_max 31.755
_cell_measurement_temperature 100(2)
_exptl_crystal_description block
_exptl_crystal_colour 'dark green'
_exptl_crystal_size_max 0.38
_exptl_crystal_size_mid 0.31
_exptl_crystal_size_min 0.23
_exptl_crystal_density_diffrn 1.272
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 932
_exptl_absorpt_coefficient_mu 0.251
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'Apex2 v2013.2-0 (Bruker, 2013)'
_exptl_absorpt_correction_T_min 0.7105
_exptl_absorpt_correction_T_max 0.7463
#==============================================================================
# EXPERIMENTAL DATA
_exptl_special_details ?
_diffrn_ambient_temperature 100(2)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Bruker APEX-II CCD diffractometer'
_diffrn_measurement_method '\f and \w scans'
_diffrn_reflns_number 92328
_diffrn_reflns_av_R_equivalents 0.0202
_diffrn_reflns_theta_min 1.501
_diffrn_reflns_theta_max 31.81
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_ful 1
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 22
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_limit_l_max 22
_diffrn_standards_number 0
_diffrn_standards_decay_% 0
#==============================================================================
# REFINEMENT DATA
_refine_special_details ?
_reflns_number_total 15250
_reflns_number_gt 12861
_reflns_threshold_expression 'I > 2\s(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0621
_refine_ls_R_factor_gt 0.0542
_refine_ls_wR_factor_ref 0.1564
_refine_ls_goodness_of_fit_ref 1.077
_refine_ls_restrained_S_all 1.08
_refine_ls_number_reflns 15250
_refine_ls_number_parameters 589
_refine_ls_number_restraints 1
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0821P)^2^+1.1311P]
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0
_refine_diff_density_max 0.931
_refine_diff_density_min -1.097
_refine_diff_density_rms 0.065
_refine_ls_extinction_method none
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'APEX2 (Bruker, 2013)'
_computing_cell_refinement 'APEX2 & SAINT (Bruker, 2013)'
_computing_data_reduction SAINT
_computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement
;
SHELXL-2013 (Sheldrick, 2013; Sheldrick, 2008)
;
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 1997) and Mercury CSD (Macrae et
al., 2008)
;
_computing_publication_material
;
WinGX (Farrugia, 1999) and publCIF (Westrip, 2010)
;
#==============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N21 0.70997(9) 0.91903(7) 0.42027(7) 0.01467(17) Uani d 1 . . N
N22 0.81110(10) 1.00477(8) 0.49974(8) 0.01821(19) Uani d 1 . . N
N23 0.88530(9) 0.80204(8) 0.64183(8) 0.01895(19) Uani d 1 . . N
N24 0.82982(9) 0.70790(7) 0.53291(7) 0.01474(17) Uani d 1 . . N
N26 0.56313(9) 0.78386(7) 0.58354(7) 0.01454(17) Uani d 1 . . N
N37 0.81510(9) 0.78568(7) 0.29766(7) 0.01497(17) Uani d 1 . . N
C1 0.64478(10) 0.86530(8) 0.40128(8) 0.01413(18) Uani d 1 . . C
C2 0.59715(10) 0.93924(9) 0.30575(8) 0.0170(2) Uani d 1 . . C
C2A 0.51399(13) 0.91987(11) 0.26540(10) 0.0253(3) Uani d 1 . . C
H2A1 0.434 0.9329 0.3031 0.038 Uiso calc 1 . . H
H2A2 0.5408 0.8481 0.2705 0.038 Uiso calc 1 . . H
H2A3 0.5126 0.9659 0.1961 0.038 Uiso calc 1 . . H
C3 0.63886(11) 1.02233(9) 0.27100(8) 0.0177(2) Uani d 1 . . C
C3A 0.63099(12) 1.11149(11) 0.17440(9) 0.0248(2) Uani d 1 . . C
H3A1 0.7099 1.1079 0.1339 0.037 Uiso calc 1 . . H
H3A2 0.6016 1.1761 0.1858 0.037 Uiso calc 1 . . H
H3A3 0.5764 1.1089 0.1402 0.037 Uiso calc 1 . . H
C4 0.70176(10) 1.00932(8) 0.34683(8) 0.01559(19) Uani d 1 . . C
C5 0.73910(11) 1.09199(9) 0.34241(9) 0.0180(2) Uani d 1 . . C
H5 0.7331 1.1525 0.2842 0.022 Uiso calc 1 . . H
C6 0.78278(10) 1.08942(9) 0.41647(9) 0.0171(2) Uani d 1 . . C
C7 0.80243(11) 1.17557(9) 0.42529(9) 0.0191(2) Uani d 1 . . C
C7A 0.77943(12) 1.28294(10) 0.35007(10) 0.0239(2) Uani d 1 . . C
H7A1 0.787 1.3295 0.3759 0.036 Uiso calc 1 . . H
H7A2 0.699 1.3047 0.3351 0.036 Uiso calc 1 . . H
H7A3 0.8372 1.2851 0.2899 0.036 Uiso calc 1 . . H
C8 0.84001(12) 1.14014(10) 0.51274(10) 0.0224(2) Uani d 1 . . C
C8A 0.86428(15) 1.19989(11) 0.55841(12) 0.0313(3) Uani d 1 . . C
H8A1 0.8882 1.2611 0.5059 0.038 Uiso calc 1 . . H
H8A2 0.9308 1.1564 0.596 0.038 Uiso calc 1 . . H
C8B 0.7550(2) 1.23443(14) 0.62704(13) 0.0416(4) Uani d 1 . . C
H8B1 0.6889 1.277 0.59 0.062 Uiso calc 1 . . H
H8B2 0.7727 1.2748 0.6546 0.062 Uiso calc 1 . . H
H8B3 0.7333 1.1738 0.6806 0.062 Uiso calc 1 . . H
C9 0.84766(12) 1.03005(10) 0.56094(10) 0.0213(2) Uani d 1 . . C
C10 0.88295(14) 0.96295(10) 0.64932(11) 0.0264(3) Uani d 1 . . C
H10 0.9001 0.9907 0.6874 0.032 Uiso calc 1 . . H
C11 0.89634(12) 0.85418(10) 0.68936(10) 0.0220(2) Uani d 1 . . C
C12 0.92841(13) 0.78678(11) 0.78757(10) 0.0255(3) Uani d 1 . . C
C12A 0.93560(17) 0.82335(13) 0.86227(12) 0.0358(3) Uani d 0.587(5) A 1 C
H12A 0.9688 0.7632 0.9187 0.043 Uiso calc 0.587(5) A 1 H
H12B 0.9899 0.8686 0.8322 0.043 Uiso calc 0.587(5) A 1 H
C12B 0.8252(4) 0.8769(3) 0.8959(2) 0.0503(10) Uani d 0.587(5) A 1 C
H12C 0.7912 0.9355 0.8399 0.075 Uiso calc 0.587(5) A 1 H
H12D 0.8334 0.9022 0.9422 0.075 Uiso calc 0.587(5) A 1 H
H12E 0.7726 0.8311 0.9292 0.075 Uiso calc 0.587(5) A 1 H
C12C 0.93560(17) 0.82335(13) 0.86227(12) 0.0358(3) Uani d 0.413(5) A 2 C
H12F 0.8694 0.8861 0.8591 0.043 Uiso calc 0.413(5) A 2 H
H12G 0.9212 0.7699 0.9284 0.043 Uiso calc 0.413(5) A 2 H
C12D 1.0451(3) 0.8471(3) 0.8551(2) 0.0222(8) Uani d 0.413(5) A 2 C
H12H 1.1116 0.7851 0.8616 0.033 Uiso calc 0.413(5) A 2 H
H12I 1.0366 0.8705 0.9078 0.033 Uiso calc 0.413(5) A 2 H
H12J 1.0602 0.9015 0.791 0.033 Uiso calc 0.413(5) A 2 H
C13 0.94191(11) 0.68938(10) 0.79624(9) 0.0213(2) Uani d 1 . . C
C13A 0.97411(14) 0.59069(11) 0.88143(10) 0.0284(3) Uani d 1 . . C
H13A 0.9946 0.6042 0.931 0.043 Uiso calc 1 . . H
H13B 1.0424 0.5425 0.8586 0.043 Uiso calc 1 . . H
H13C 0.9065 0.5605 0.9106 0.043 Uiso calc 1 . . H
C14 0.91470(10) 0.69853(9) 0.70539(9) 0.0179(2) Uani d 1 . . C
C15 0.91580(10) 0.61707(9) 0.68642(9) 0.0175(2) Uani d 1 . . C
H15 0.9453 0.5506 0.7334 0.021 Uiso calc 1 . . H
C16 0.87874(10) 0.61876(8) 0.60588(8) 0.01586(19) Uani d 1 . . C
C17 0.87213(10) 0.53567(9) 0.58977(9) 0.0172(2) Uani d 1 . . C
C17A 0.91133(12) 0.42338(9) 0.65147(10) 0.0229(2) Uani d 1 . . C
H17A 0.9694 0.4126 0.6902 0.034 Uiso calc 1 . . H
H17B 0.9477 0.384 0.6086 0.034 Uiso calc 1 . . H
H17C 0.8425 0.4001 0.696 0.034 Uiso calc 1 . . H
C18 0.81592(10) 0.57684(8) 0.50671(8) 0.0161(2) Uani d 1 . . C
C18A 0.79108(12) 0.51595(9) 0.46249(10) 0.0215(2) Uani d 1 . . C
H18A 0.7309 0.5606 0.4196 0.032 Uiso calc 1 . . H
H18B 0.7618 0.4585 0.5152 0.032 Uiso calc 1 . . H
H18C 0.8643 0.4889 0.4237 0.032 Uiso calc 1 . . H
C19 0.78850(10) 0.68402(8) 0.47432(8) 0.01446(19) Uani d 1 . . C
C20 0.72644(10) 0.76254(8) 0.38942(8) 0.01419(18) Uani d 1 . . C
H20 0.6745 0.7298 0.3801 0.017 Uiso calc 1 . . H
C25 0.53614(10) 0.84911(9) 0.48398(8) 0.01572(19) Uani d 1 . . C
H25A 0.4856 0.9175 0.4841 0.019 Uiso calc 1 . . H
H25B 0.4889 0.8185 0.4676 0.019 Uiso calc 1 . . H
C27 0.56220(10) 0.68072(9) 0.63576(8) 0.01502(19) Uani d 1 . . C
C28 0.59337(10) 0.64910(9) 0.72624(8) 0.0171(2) Uani d 1 . . C
H28 0.5994 0.5825 0.7769 0.021 Uiso calc 1 . . H
C29 0.61479(10) 0.73430(9) 0.72986(8) 0.0169(2) Uani d 1 . . C
C30 0.59495(10) 0.81562(9) 0.64040(8) 0.0164(2) Uani d 1 . . C
H30 0.6025 0.8827 0.6222 0.02 Uiso calc 1 . . H
C31 0.53151(10) 0.62050(9) 0.59715(9) 0.0174(2) Uani d 1 . . C
O32 0.50649(9) 0.64960(7) 0.51630(7) 0.02194(18) Uani d 1 . . O
O33 0.53371(10) 0.52580(7) 0.66590(7) 0.0254(2) Uani d 1 . . O
C34 0.49624(15) 0.46103(11) 0.63929(12) 0.0315(3) Uani d 1 . . C
H34A 0.4141 0.4934 0.6269 0.047 Uiso calc 1 . . H
H34B 0.5013 0.3935 0.6933 0.047 Uiso calc 1 . . H
H34C 0.548 0.4523 0.5797 0.047 Uiso calc 1 . . H
C35 0.65111(11) 0.73914(10) 0.80924(9) 0.0204(2) Uani d 1 . . C
H35 0.6658 0.8016 0.7984 0.024 Uiso calc 1 . . H
O36 0.66434(9) 0.66883(8) 0.88935(7) 0.0264(2) Uani d 1 . . O
C38 0.82546(11) 0.76704(10) 0.21351(9) 0.0194(2) Uani d 1 . . C
C39 0.91770(13) 0.80331(12) 0.14612(10) 0.0269(3) Uani d 1 . . C
H39 0.9444 0.8012 0.0821 0.032 Uiso calc 1 . . H
C40 0.96525(12) 0.84420(11) 0.18959(10) 0.0229(2) Uani d 1 . . C
C41 0.90065(10) 0.83054(9) 0.28324(9) 0.0171(2) Uani d 1 . . C
H41 0.9143 0.8496 0.3299 0.021 Uiso calc 1 . . H
C42 0.75290(12) 0.71418(10) 0.20273(9) 0.0215(2) Uani d 1 . . C
O43 0.66661(10) 0.68992(9) 0.25844(8) 0.0275(2) Uani d 1 . . O
O44 0.79614(12) 0.69403(12) 0.12047(9) 0.0418(3) Uani d 1 . . O
C45 0.73003(19) 0.6436(2) 0.10148(15) 0.0493(5) Uani d 1 . . C
H45A 0.7293 0.5769 0.1557 0.074 Uiso calc 1 . . H
H45B 0.7675 0.6327 0.0397 0.074 Uiso calc 1 . . H
H45C 0.6484 0.6868 0.0961 0.074 Uiso calc 1 . . H
C46A 1.06300(15) 0.89208(15) 0.14581(12) 0.0365(4) Uani d 0.668(4) B 1 C
H46A 1.0965 0.9024 0.0789 0.044 Uiso calc 0.668(4) B 1 H
O47A 1.10462(16) 0.91996(15) 0.19050(13) 0.0347(5) Uani d 0.668(4) B 1 O
C46B 1.06300(15) 0.89208(15) 0.14581(12) 0.0365(4) Uani d 0.332(4) B 2 C
H46B 1.1047 0.8947 0.1879 0.044 Uiso calc 0.332(4) B 2 H
O47B 1.0951(5) 0.9313(5) 0.0513(3) 0.0604(17) Uani d 0.332(4) B 2 O
H22 0.8105(19) 0.9472(18) 0.5093(16) 0.036(5) Uiso d 1 . . H
H24 0.8202(16) 0.7665(15) 0.5293(14) 0.023(4) Uiso d 1 . . H
C1S 0.30459(17) 0.57146(14) 0.01659(13) 0.0383(4) Uani d 1 C 2 C
H1S 0.3249 0.4948 0.0514 0.046 Uiso calc 1 C 2 H
Cl1 0.16719(6) 0.62496(5) 0.07528(4) 0.06145(16) Uani d 1 C 2 Cl
Cl2 0.29793(7) 0.60167(5) -0.10615(4) 0.06313(16) Uani d 1 C 2 Cl
Cl3 0.41664(7) 0.61621(5) 0.01980(7) 0.0864(3) Uani d 1 C 2 Cl
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N21 0.0183(4) 0.0123(4) 0.0139(4) -0.0043(3) -0.0027(3) -0.0052(3)
N22 0.0242(5) 0.0125(4) 0.0198(5) -0.0075(4) -0.0062(4) -0.0039(3)
N23 0.0210(5) 0.0162(4) 0.0191(4) -0.0073(4) -0.0071(4) -0.0019(4)
N24 0.0182(4) 0.0107(4) 0.0143(4) -0.0034(3) -0.0038(3) -0.0035(3)
N26 0.0168(4) 0.0145(4) 0.0126(4) -0.0047(3) -0.0018(3) -0.0053(3)
N37 0.0178(4) 0.0150(4) 0.0134(4) -0.0059(3) -0.0009(3) -0.0063(3)
C1 0.0171(5) 0.0129(4) 0.0126(4) -0.0040(4) -0.0032(3) -0.0045(3)
C2 0.0193(5) 0.0175(5) 0.0134(4) -0.0032(4) -0.0044(4) -0.0054(4)
C2A 0.0299(6) 0.0283(6) 0.0207(6) -0.0090(5) -0.0112(5) -0.0065(5)
C3 0.0194(5) 0.0169(5) 0.0133(4) -0.0031(4) -0.0032(4) -0.0037(4)
C3A 0.0275(6) 0.0234(6) 0.0156(5) -0.0067(5) -0.0056(4) 0.0009(4)
C4 0.0173(5) 0.0134(4) 0.0145(4) -0.0033(4) -0.0019(4) -0.0048(4)
C5 0.0222(5) 0.0126(4) 0.0168(5) -0.0054(4) -0.0025(4) -0.0031(4)
C6 0.0179(5) 0.0132(4) 0.0192(5) -0.0054(4) -0.0008(4) -0.0056(4)
C7 0.0198(5) 0.0139(5) 0.0235(5) -0.0077(4) -0.0010(4) -0.0062(4)
C7A 0.0263(6) 0.0145(5) 0.0280(6) -0.0093(4) -0.0017(5) -0.0040(4)
C8 0.0263(6) 0.0173(5) 0.0276(6) -0.0111(4) -0.0054(5) -0.0072(4)
C8A 0.0453(8) 0.0225(6) 0.0359(7) -0.0186(6) -0.0150(6) -0.0067(5)
C8B 0.0716(12) 0.0355(8) 0.0324(8) -0.0283(8) -0.0042(8) -0.0171(7)
C9 0.0257(6) 0.0175(5) 0.0245(6) -0.0099(4) -0.0076(4) -0.0059(4)
C10 0.0362(7) 0.0210(6) 0.0287(6) -0.0133(5) -0.0153(5) -0.0047(5)
C11 0.0262(6) 0.0200(5) 0.0221(5) -0.0104(4) -0.0105(5) -0.0025(4)
C12 0.0318(6) 0.0252(6) 0.0233(6) -0.0112(5) -0.0145(5) -0.0033(5)
C12A 0.0530(10) 0.0321(7) 0.0327(7) -0.0139(7) -0.0236(7) -0.0090(6)
C12B 0.070(2) 0.0501(19) 0.0313(15) -0.0004(16) -0.0138(14) -0.0239(14)
C12C 0.0530(10) 0.0321(7) 0.0327(7) -0.0139(7) -0.0236(7) -0.0090(6)
C12D 0.0230(14) 0.0296(16) 0.0193(14) -0.0114(12) -0.0048(10) -0.0096(11)
C13 0.0227(5) 0.0225(5) 0.0178(5) -0.0080(4) -0.0087(4) -0.0017(4)
C13A 0.0348(7) 0.0256(6) 0.0209(6) -0.0077(5) -0.0129(5) -0.0003(5)
C14 0.0172(5) 0.0181(5) 0.0163(5) -0.0065(4) -0.0050(4) -0.0018(4)
C15 0.0166(5) 0.0150(5) 0.0161(5) -0.0036(4) -0.0039(4) -0.0015(4)
C16 0.0161(5) 0.0124(4) 0.0154(5) -0.0033(4) -0.0028(4) -0.0023(4)
C17 0.0167(5) 0.0121(4) 0.0190(5) -0.0038(4) -0.0002(4) -0.0041(4)
C17A 0.0238(6) 0.0126(5) 0.0255(6) -0.0043(4) -0.0038(4) -0.0018(4)
C18 0.0170(5) 0.0126(4) 0.0177(5) -0.0049(4) 0.0009(4) -0.0064(4)
C18A 0.0244(6) 0.0162(5) 0.0268(6) -0.0067(4) -0.0008(4) -0.0117(4)
C19 0.0165(4) 0.0127(4) 0.0138(4) -0.0043(4) -0.0014(3) -0.0049(4)
C20 0.0171(5) 0.0135(4) 0.0127(4) -0.0050(4) -0.0011(3) -0.0057(4)
C25 0.0169(5) 0.0154(5) 0.0134(4) -0.0033(4) -0.0027(4) -0.0047(4)
C27 0.0160(5) 0.0150(5) 0.0148(4) -0.0061(4) -0.0009(4) -0.0057(4)
C28 0.0189(5) 0.0172(5) 0.0144(5) -0.0069(4) -0.0019(4) -0.0041(4)
C29 0.0188(5) 0.0193(5) 0.0143(5) -0.0071(4) -0.0009(4) -0.0072(4)
C30 0.0191(5) 0.0168(5) 0.0149(5) -0.0058(4) -0.0013(4) -0.0075(4)
C31 0.0164(5) 0.0179(5) 0.0198(5) -0.0075(4) 0.0004(4) -0.0087(4)
O32 0.0262(4) 0.0234(4) 0.0212(4) -0.0091(3) -0.0053(3) -0.0100(3)
O33 0.0367(5) 0.0194(4) 0.0248(4) -0.0162(4) -0.0059(4) -0.0049(4)
C34 0.0401(8) 0.0243(6) 0.0389(8) -0.0189(6) -0.0066(6) -0.0115(6)
C35 0.0225(5) 0.0257(6) 0.0162(5) -0.0095(4) -0.0016(4) -0.0093(4)
O36 0.0314(5) 0.0332(5) 0.0158(4) -0.0128(4) -0.0052(3) -0.0060(4)
C38 0.0233(5) 0.0241(5) 0.0148(5) -0.0101(4) -0.0002(4) -0.0097(4)
C39 0.0309(7) 0.0385(7) 0.0178(5) -0.0186(6) 0.0040(5) -0.0138(5)
C40 0.0239(6) 0.0277(6) 0.0202(5) -0.0133(5) 0.0018(4) -0.0098(5)
C41 0.0178(5) 0.0167(5) 0.0182(5) -0.0055(4) -0.0019(4) -0.0077(4)
C42 0.0274(6) 0.0249(6) 0.0180(5) -0.0101(5) -0.0023(4) -0.0113(4)
O43 0.0325(5) 0.0363(5) 0.0251(5) -0.0200(4) 0.0027(4) -0.0175(4)
O44 0.0471(7) 0.0732(9) 0.0307(6) -0.0358(7) 0.0107(5) -0.0368(6)
C45 0.0539(11) 0.0801(15) 0.0472(10) -0.0346(10) 0.0045(8) -0.0477(11)
C46A 0.0356(8) 0.0552(10) 0.0297(7) -0.0307(7) 0.0090(6) -0.0197(7)
O47A 0.0396(10) 0.0407(10) 0.0331(9) -0.0255(8) 0.0020(7) -0.0152(7)
C46B 0.0356(8) 0.0552(10) 0.0297(7) -0.0307(7) 0.0090(6) -0.0197(7)
O47B 0.065(3) 0.108(4) 0.0250(19) -0.069(3) 0.0102(17) -0.014(2)
C1S 0.0424(9) 0.0333(8) 0.0329(8) -0.0168(7) -0.0090(7) 0.0004(6)
Cl1 0.0686(4) 0.0502(3) 0.0472(3) -0.0186(3) 0.0152(2) -0.0153(2)
Cl2 0.0836(4) 0.0633(3) 0.0309(2) -0.0203(3) -0.0069(2) -0.0084(2)
Cl3 0.0740(4) 0.0522(3) 0.1267(7) -0.0317(3) -0.0600(5) 0.0109(4)
#==============================================================================
# MOLECULAR GEOMETRY
_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N21 C4 . 1.3174(14) ?
N21 C1 . 1.4710(14) ?
N22 C6 . 1.3691(15) ?
N22 C9 . 1.3769(16) ?
N22 H22 . 0.81(2) ?
N23 C11 . 1.3376(16) ?
N23 C14 . 1.3999(15) ?
N24 C19 . 1.3641(14) ?
N24 C16 . 1.3765(14) ?
N24 H24 . 0.821(19) ?
N26 C30 . 1.3516(14) ?
N26 C27 . 1.3960(14) ?
N26 C25 . 1.4623(14) ?
N37 C41 . 1.3523(15) ?
N37 C38 . 1.3961(14) ?
N37 C20 . 1.4903(14) ?
C1 C2 . 1.5210(15) ?
C1 C25 . 1.5509(16) ?
C1 C20 . 1.5629(15) ?
C2 C3 . 1.3437(17) ?
C2 C2A . 1.4931(17) ?
C2A H2A1 . 0.98 ?
C2A H2A2 . 0.98 ?
C2A H2A3 . 0.98 ?
C3 C4 . 1.4788(16) ?
C3 C3A . 1.4948(16) ?
C3A H3A1 . 0.98 ?
C3A H3A2 . 0.98 ?
C3A H3A3 . 0.98 ?
C4 C5 . 1.4348(16) ?
C5 C6 . 1.3670(17) ?
C5 H5 . 0.95 ?
C6 C7 . 1.4614(16) ?
C7 C8 . 1.3572(18) ?
C7 C7A . 1.4932(17) ?
C7A H7A1 . 0.98 ?
C7A H7A2 . 0.98 ?
C7A H7A3 . 0.98 ?
C8 C9 . 1.4609(17) ?
C8 C8A . 1.4958(18) ?
C8A C8B . 1.524(3) ?
C8A H8A1 . 0.99 ?
C8A H8A2 . 0.99 ?
C8B H8B1 . 0.98 ?
C8B H8B2 . 0.98 ?
C8B H8B3 . 0.98 ?
C9 C10 . 1.3638(18) ?
C10 C11 . 1.4314(18) ?
C10 H10 . 0.95 ?
C11 C12 . 1.4688(18) ?
C12 C13 . 1.3584(19) ?
C12 C12A . 1.503(2) ?
C12A C12B . 1.384(4) ?
C12A H12A . 0.99 ?
C12A H12B . 0.99 ?
C12B H12C . 0.98 ?
C12B H12D . 0.98 ?
C12B H12E . 0.98 ?
C12D H12H . 0.98 ?
C12D H12I . 0.98 ?
C12D H12J . 0.98 ?
C13 C14 . 1.4597(17) ?
C13 C13A . 1.4931(18) ?
C13A H13A . 0.98 ?
C13A H13B . 0.98 ?
C13A H13C . 0.98 ?
C14 C15 . 1.3683(17) ?
C15 C16 . 1.4188(16) ?
C15 H15 . 0.95 ?
C16 C17 . 1.4038(16) ?
C17 C18 . 1.4081(17) ?
C17 C17A . 1.4977(16) ?
C17A H17A . 0.98 ?
C17A H17B . 0.98 ?
C17A H17C . 0.98 ?
C18 C19 . 1.3963(15) ?
C18 C18A . 1.4972(16) ?
C18A H18A . 0.98 ?
C18A H18B . 0.98 ?
C18A H18C . 0.98 ?
C19 C20 . 1.4962(15) ?
C20 H20 . 1 ?
C25 H25A . 0.99 ?
C25 H25B . 0.99 ?
C27 C28 . 1.3738(15) ?
C27 C31 . 1.4637(15) ?
C28 C29 . 1.4178(16) ?
C28 H28 . 0.95 ?
C29 C30 . 1.3905(16) ?
C29 C35 . 1.4462(16) ?
C30 H30 . 0.95 ?
C31 O32 . 1.2103(15) ?
C31 O33 . 1.3409(15) ?
O33 C34 . 1.4456(16) ?
C34 H34A . 0.98 ?
C34 H34B . 0.98 ?
C34 H34C . 0.98 ?
C35 O36 . 1.2236(16) ?
C35 H35 . 0.95 ?
C38 C39 . 1.3773(17) ?
C38 C42 . 1.4630(17) ?
C39 C40 . 1.4114(18) ?
C39 H39 . 0.95 ?
C40 C41 . 1.3853(17) ?
C40 C46A . 1.4535(19) ?
C41 H41 . 0.95 ?
C42 O43 . 1.2035(17) ?
C42 O44 . 1.3375(15) ?
O44 C45 . 1.440(2) ?
C45 H45A . 0.98 ?
C45 H45B . 0.98 ?
C45 H45C . 0.98 ?
C46A O47A . 1.227(2) ?
C46A H46A . 0.95 ?
C1S Cl3 . 1.7456(19) ?
C1S Cl2 . 1.7479(19) ?
C1S Cl1 . 1.750(2) ?
C1S H1S . 1 ?
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
C4 N21 C1 106.34(9) . . ?
C6 N22 C9 110.54(10) . . ?
C6 N22 H22 124.1(16) . . ?
C9 N22 H22 125.2(16) . . ?
C11 N23 C14 104.79(10) . . ?
C19 N24 C16 109.57(9) . . ?
C19 N24 H24 125.3(13) . . ?
C16 N24 H24 124.8(13) . . ?
C30 N26 C27 108.45(9) . . ?
C30 N26 C25 124.13(10) . . ?
C27 N26 C25 127.41(9) . . ?
C41 N37 C38 108.45(10) . . ?
C41 N37 C20 123.73(9) . . ?
C38 N37 C20 127.82(10) . . ?
N21 C1 C2 105.86(9) . . ?
N21 C1 C25 108.83(9) . . ?
C2 C1 C25 107.26(9) . . ?
N21 C1 C20 112.18(9) . . ?
C2 C1 C20 109.63(9) . . ?
C25 C1 C20 112.74(9) . . ?
C3 C2 C2A 128.87(11) . . ?
C3 C2 C1 107.60(10) . . ?
C2A C2 C1 123.46(10) . . ?
C2 C2A H2A1 109.5 . . ?
C2 C2A H2A2 109.5 . . ?
H2A1 C2A H2A2 109.5 . . ?
C2 C2A H2A3 109.5 . . ?
H2A1 C2A H2A3 109.5 . . ?
H2A2 C2A H2A3 109.5 . . ?
C2 C3 C4 106.70(10) . . ?
C2 C3 C3A 129.43(11) . . ?
C4 C3 C3A 123.84(11) . . ?
C3 C3A H3A1 109.5 . . ?
C3 C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 109.5 . . ?
C3 C3A H3A3 109.5 . . ?
H3A1 C3A H3A3 109.5 . . ?
H3A2 C3A H3A3 109.5 . . ?
N21 C4 C5 124.96(11) . . ?
N21 C4 C3 113.13(10) . . ?
C5 C4 C3 121.68(10) . . ?
C6 C5 C4 124.33(11) . . ?
C6 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
C5 C6 N22 125.59(11) . . ?
C5 C6 C7 127.44(11) . . ?
N22 C6 C7 106.90(10) . . ?
C8 C7 C6 107.93(10) . . ?
C8 C7 C7A 128.25(11) . . ?
C6 C7 C7A 123.79(11) . . ?
C7 C7A H7A1 109.5 . . ?
C7 C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C7 C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C7 C8 C9 107.93(11) . . ?
C7 C8 C8A 128.30(12) . . ?
C9 C8 C8A 123.69(12) . . ?
C8 C8A C8B 111.15(13) . . ?
C8 C8A H8A1 109.4 . . ?
C8B C8A H8A1 109.4 . . ?
C8 C8A H8A2 109.4 . . ?
C8B C8A H8A2 109.4 . . ?
H8A1 C8A H8A2 108 . . ?
C8A C8B H8B1 109.5 . . ?
C8A C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
C8A C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
C10 C9 N22 125.13(11) . . ?
C10 C9 C8 128.18(12) . . ?
N22 C9 C8 106.69(11) . . ?
C9 C10 C11 125.36(12) . . ?
C9 C10 H10 117.3 . . ?
C11 C10 H10 117.3 . . ?
N23 C11 C10 124.73(11) . . ?
N23 C11 C12 112.52(11) . . ?
C10 C11 C12 122.72(12) . . ?
C13 C12 C11 105.66(11) . . ?
C13 C12 C12A 129.20(12) . . ?
C11 C12 C12A 125.03(13) . . ?
C12B C12A C12 111.54(19) . . ?
C12B C12A H12A 109.3 . . ?
C12 C12A H12A 109.3 . . ?
C12B C12A H12B 109.3 . . ?
C12 C12A H12B 109.3 . . ?
H12A C12A H12B 108 . . ?
C12A C12B H12C 109.5 . . ?
C12A C12B H12D 109.5 . . ?
H12C C12B H12D 109.5 . . ?
C12A C12B H12E 109.5 . . ?
H12C C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12H C12D H12I 109.5 . . ?
H12H C12D H12J 109.5 . . ?
H12I C12D H12J 109.5 . . ?
C12 C13 C14 106.47(11) . . ?
C12 C13 C13A 128.39(12) . . ?
C14 C13 C13A 125.12(12) . . ?
C13 C13A H13A 109.5 . . ?
C13 C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C13 C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C15 C14 N23 125.10(11) . . ?
C15 C14 C13 124.40(11) . . ?
N23 C14 C13 110.49(11) . . ?
C14 C15 C16 128.54(11) . . ?
C14 C15 H15 115.7 . . ?
C16 C15 H15 115.7 . . ?
N24 C16 C17 107.38(10) . . ?
N24 C16 C15 123.72(10) . . ?
C17 C16 C15 128.59(10) . . ?
C16 C17 C18 107.54(10) . . ?
C16 C17 C17A 127.11(11) . . ?
C18 C17 C17A 125.28(11) . . ?
C17 C17A H17A 109.5 . . ?
C17 C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C17 C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C19 C18 C17 106.98(10) . . ?
C19 C18 C18A 127.15(11) . . ?
C17 C18 C18A 125.87(10) . . ?
C18 C18A H18A 109.5 . . ?
C18 C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C18 C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
N24 C19 C18 108.46(10) . . ?
N24 C19 C20 123.95(10) . . ?
C18 C19 C20 127.59(10) . . ?
N37 C20 C19 109.63(9) . . ?
N37 C20 C1 109.77(9) . . ?
C19 C20 C1 116.61(9) . . ?
N37 C20 H20 106.8 . . ?
C19 C20 H20 106.8 . . ?
C1 C20 H20 106.8 . . ?
N26 C25 C1 115.89(9) . . ?
N26 C25 H25A 108.3 . . ?
C1 C25 H25A 108.3 . . ?
N26 C25 H25B 108.3 . . ?
C1 C25 H25B 108.3 . . ?
H25A C25 H25B 107.4 . . ?
C28 C27 N26 108.33(10) . . ?
C28 C27 C31 127.88(11) . . ?
N26 C27 C31 123.79(10) . . ?
C27 C28 C29 107.24(10) . . ?
C27 C28 H28 126.4 . . ?
C29 C28 H28 126.4 . . ?
C30 C29 C28 106.90(10) . . ?
C30 C29 C35 124.90(11) . . ?
C28 C29 C35 128.19(11) . . ?
N26 C30 C29 109.07(10) . . ?
N26 C30 H30 125.5 . . ?
C29 C30 H30 125.5 . . ?
O32 C31 O33 123.66(11) . . ?
O32 C31 C27 126.62(11) . . ?
O33 C31 C27 109.72(10) . . ?
C31 O33 C34 115.07(11) . . ?
O33 C34 H34A 109.5 . . ?
O33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O36 C35 C29 124.93(12) . . ?
O36 C35 H35 117.5 . . ?
C29 C35 H35 117.5 . . ?
C39 C38 N37 107.89(11) . . ?
C39 C38 C42 127.18(11) . . ?
N37 C38 C42 124.88(11) . . ?
C38 C39 C40 107.51(11) . . ?
C38 C39 H39 126.2 . . ?
C40 C39 H39 126.2 . . ?
C41 C40 C39 106.96(11) . . ?
C41 C40 C46A 125.71(12) . . ?
C39 C40 C46A 127.33(12) . . ?
N37 C41 C40 109.16(10) . . ?
N37 C41 H41 125.4 . . ?
C40 C41 H41 125.4 . . ?
O43 C42 O44 122.75(12) . . ?
O43 C42 C38 126.79(11) . . ?
O44 C42 C38 110.46(11) . . ?
C42 O44 C45 115.20(13) . . ?
O44 C45 H45A 109.5 . . ?
O44 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
O44 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
O47A C46A C40 123.62(15) . . ?
O47A C46A H46A 118.2 . . ?
C40 C46A H46A 118.2 . . ?
Cl3 C1S Cl2 108.93(10) . . ?
Cl3 C1S Cl1 111.30(12) . . ?
Cl2 C1S Cl1 110.50(10) . . ?
Cl3 C1S H1S 108.7 . . ?
Cl2 C1S H1S 108.7 . . ?
Cl1 C1S H1S 108.7 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N21 C1 C2 -0.37(11) . . . . ?
C4 N21 C1 C25 -115.38(10) . . . . ?
C4 N21 C1 C20 119.16(10) . . . . ?
N21 C1 C2 C3 4.18(12) . . . . ?
C25 C1 C2 C3 120.27(10) . . . . ?
C20 C1 C2 C3 -117.01(11) . . . . ?
N21 C1 C2 C2A -172.91(11) . . . . ?
C25 C1 C2 C2A -56.83(14) . . . . ?
C20 C1 C2 C2A 65.90(14) . . . . ?
C2A C2 C3 C4 170.95(12) . . . . ?
C1 C2 C3 C4 -5.93(13) . . . . ?
C2A C2 C3 C3A -11.1(2) . . . . ?
C1 C2 C3 C3A 171.99(12) . . . . ?
C1 N21 C4 C5 171.24(11) . . . . ?
C1 N21 C4 C3 -3.34(13) . . . . ?
C2 C3 C4 N21 6.20(14) . . . . ?
C3A C3 C4 N21 -171.87(11) . . . . ?
C2 C3 C4 C5 -168.59(11) . . . . ?
C3A C3 C4 C5 13.35(18) . . . . ?
N21 C4 C5 C6 -3.43(19) . . . . ?
C3 C4 C5 C6 170.71(11) . . . . ?
C4 C5 C6 N22 8.5(2) . . . . ?
C4 C5 C6 C7 -168.07(11) . . . . ?
C9 N22 C6 C5 -177.33(12) . . . . ?
C9 N22 C6 C7 -0.18(14) . . . . ?
C5 C6 C7 C8 176.43(12) . . . . ?
N22 C6 C7 C8 -0.65(14) . . . . ?
C5 C6 C7 C7A -1.7(2) . . . . ?
N22 C6 C7 C7A -178.75(11) . . . . ?
C6 C7 C8 C9 1.17(14) . . . . ?
C7A C7 C8 C9 179.16(12) . . . . ?
C6 C7 C8 C8A -175.67(14) . . . . ?
C7A C7 C8 C8A 2.3(2) . . . . ?
C7 C8 C8A C8B 92.82(18) . . . . ?
C9 C8 C8A C8B -83.57(18) . . . . ?
C6 N22 C9 C10 -179.44(14) . . . . ?
C6 N22 C9 C8 0.89(14) . . . . ?
C7 C8 C9 C10 179.05(15) . . . . ?
C8A C8 C9 C10 -3.9(2) . . . . ?
C7 C8 C9 N22 -1.29(15) . . . . ?
C8A C8 C9 N22 175.74(13) . . . . ?
N22 C9 C10 C11 5.0(2) . . . . ?
C8 C9 C10 C11 -175.38(14) . . . . ?
C14 N23 C11 C10 175.46(13) . . . . ?
C14 N23 C11 C12 -2.47(15) . . . . ?
C9 C10 C11 N23 5.7(2) . . . . ?
C9 C10 C11 C12 -176.54(14) . . . . ?
N23 C11 C12 C13 2.72(16) . . . . ?
C10 C11 C12 C13 -175.26(13) . . . . ?
N23 C11 C12 C12A -173.76(14) . . . . ?
C10 C11 C12 C12A 8.3(2) . . . . ?
C13 C12 C12A C12B -109.4(2) . . . . ?
C11 C12 C12A C12B 66.2(3) . . . . ?
C11 C12 C13 C14 -1.66(15) . . . . ?
C12A C12 C13 C14 174.62(15) . . . . ?
C11 C12 C13 C13A -179.83(13) . . . . ?
C12A C12 C13 C13A -3.5(3) . . . . ?
C11 N23 C14 C15 -179.80(12) . . . . ?
C11 N23 C14 C13 1.37(14) . . . . ?
C12 C13 C14 C15 -178.56(12) . . . . ?
C13A C13 C14 C15 -0.3(2) . . . . ?
C12 C13 C14 N23 0.28(15) . . . . ?
C13A C13 C14 N23 178.53(12) . . . . ?
N23 C14 C15 C16 -6.1(2) . . . . ?
C13 C14 C15 C16 172.57(12) . . . . ?
C19 N24 C16 C17 2.50(13) . . . . ?
C19 N24 C16 C15 -171.54(11) . . . . ?
C14 C15 C16 N24 -2.4(2) . . . . ?
C14 C15 C16 C17 -175.15(12) . . . . ?
N24 C16 C17 C18 -1.20(13) . . . . ?
C15 C16 C17 C18 172.45(11) . . . . ?
N24 C16 C17 C17A -178.34(11) . . . . ?
C15 C16 C17 C17A -4.7(2) . . . . ?
C16 C17 C18 C19 -0.48(13) . . . . ?
C17A C17 C18 C19 176.72(11) . . . . ?
C16 C17 C18 C18A 179.48(11) . . . . ?
C17A C17 C18 C18A -3.32(19) . . . . ?
C16 N24 C19 C18 -2.83(13) . . . . ?
C16 N24 C19 C20 178.06(10) . . . . ?
C17 C18 C19 N24 2.01(13) . . . . ?
C18A C18 C19 N24 -177.95(11) . . . . ?
C17 C18 C19 C20 -178.92(11) . . . . ?
C18A C18 C19 C20 1.12(19) . . . . ?
C41 N37 C20 C19 -64.66(13) . . . . ?
C38 N37 C20 C19 115.80(12) . . . . ?
C41 N37 C20 C1 64.65(13) . . . . ?
C38 N37 C20 C1 -114.89(12) . . . . ?
N24 C19 C20 N37 90.52(12) . . . . ?
C18 C19 C20 N37 -88.41(13) . . . . ?
N24 C19 C20 C1 -34.96(15) . . . . ?
C18 C19 C20 C1 146.11(11) . . . . ?
N21 C1 C20 N37 -67.32(11) . . . . ?
C2 C1 C20 N37 49.98(12) . . . . ?
C25 C1 C20 N37 169.39(9) . . . . ?
N21 C1 C20 C19 58.10(12) . . . . ?
C2 C1 C20 C19 175.40(9) . . . . ?
C25 C1 C20 C19 -65.20(12) . . . . ?
C30 N26 C25 C1 78.06(14) . . . . ?
C27 N26 C25 C1 -101.29(13) . . . . ?
N21 C1 C25 N26 -62.96(12) . . . . ?
C2 C1 C25 N26 -177.06(9) . . . . ?
C20 C1 C25 N26 62.17(12) . . . . ?
C30 N26 C27 C28 0.32(13) . . . . ?
C25 N26 C27 C28 179.75(10) . . . . ?
C30 N26 C27 C31 179.87(10) . . . . ?
C25 N26 C27 C31 -0.69(17) . . . . ?
N26 C27 C28 C29 -0.37(13) . . . . ?
C31 C27 C28 C29 -179.91(11) . . . . ?
C27 C28 C29 C30 0.30(13) . . . . ?
C27 C28 C29 C35 -179.32(12) . . . . ?
C27 N26 C30 C29 -0.13(13) . . . . ?
C25 N26 C30 C29 -179.59(10) . . . . ?
C28 C29 C30 N26 -0.10(13) . . . . ?
C35 C29 C30 N26 179.53(11) . . . . ?
C28 C27 C31 O32 -178.49(12) . . . . ?
N26 C27 C31 O32 2.05(19) . . . . ?
C28 C27 C31 O33 2.13(17) . . . . ?
N26 C27 C31 O33 -177.34(10) . . . . ?
O32 C31 O33 C34 -3.81(18) . . . . ?
C27 C31 O33 C34 175.60(11) . . . . ?
C30 C29 C35 O36 177.15(13) . . . . ?
C28 C29 C35 O36 -3.3(2) . . . . ?
C41 N37 C38 C39 -1.22(15) . . . . ?
C20 N37 C38 C39 178.38(11) . . . . ?
C41 N37 C38 C42 176.47(12) . . . . ?
C20 N37 C38 C42 -3.9(2) . . . . ?
N37 C38 C39 C40 0.38(16) . . . . ?
C42 C38 C39 C40 -177.24(13) . . . . ?
C38 C39 C40 C41 0.56(17) . . . . ?
C38 C39 C40 C46A -179.28(16) . . . . ?
C38 N37 C41 C40 1.59(14) . . . . ?
C20 N37 C41 C40 -178.03(11) . . . . ?
C39 C40 C41 N37 -1.33(15) . . . . ?
C46A C40 C41 N37 178.52(15) . . . . ?
C39 C38 C42 O43 -173.69(15) . . . . ?
N37 C38 C42 O43 9.1(2) . . . . ?
C39 C38 C42 O44 6.9(2) . . . . ?
N37 C38 C42 O44 -170.30(13) . . . . ?
O43 C42 O44 C45 1.7(2) . . . . ?
C38 C42 O44 C45 -178.92(16) . . . . ?
C41 C40 C46A O47A 5.1(3) . . . . ?
C39 C40 C46A O47A -175.08(19) . . . . ?
_shelxl_version_number 0.000002012
_iucr_refine_instructions_details
;
TITL gmf13036
CELL 0.71073 12.2119 14.9841 15.3037 63.927 73.114 69.089
ZERR 2.00 0.0003 0.0003 0.0003 0.001 0.001 0.001
LATT 1
SFAC C H CL N O
UNIT 92 98 6 12 12
MERG 2
OMIT -1 1 1
OMIT -2 0 2
OMIT -3 0 1
EXYZ C12A C12C
EADP C12A C12C
EXYZ C46A C46B
EADP C46A C46B
DFIX 1.200 0.010 C46A O47B
FMAP 2
PLAN 20
SIZE 0.23 0.31 0.38
ACTA
BOND $H
CONF
LIST 4
L.S. 16
TEMP -173.00
WGHT 0.082100 1.131100
FVAR 1.69210 0.58720 0.66768
MOLE 1
N21 4 0.709972 0.919028 0.420266 11.00000 0.01830 0.01232 =
0.01388 -0.00516 -0.00265 -0.00425
N22 4 0.811096 1.004770 0.499739 11.00000 0.02417 0.01246 =
0.01978 -0.00393 -0.00622 -0.00746
N23 4 0.885296 0.802043 0.641829 11.00000 0.02098 0.01624 =
0.01911 -0.00192 -0.00713 -0.00729
N24 4 0.829822 0.707904 0.532914 11.00000 0.01821 0.01074 =
0.01434 -0.00352 -0.00375 -0.00341
N26 4 0.563133 0.783860 0.583538 11.00000 0.01684 0.01449 =
0.01259 -0.00528 -0.00177 -0.00474
N37 4 0.815102 0.785682 0.297662 11.00000 0.01779 0.01504 =
0.01337 -0.00632 -0.00087 -0.00587
C1 1 0.644780 0.865302 0.401280 11.00000 0.01708 0.01290 =
0.01261 -0.00447 -0.00318 -0.00399
C2 1 0.597148 0.939243 0.305746 11.00000 0.01933 0.01754 =
0.01336 -0.00538 -0.00441 -0.00319
C2A 1 0.513987 0.919865 0.265398 11.00000 0.02994 0.02829 =
0.02069 -0.00645 -0.01118 -0.00897
AFIX 137
H2A1 2 0.434011 0.932895 0.303098 11.00000 -1.50000
H2A2 2 0.540794 0.848053 0.270528 11.00000 -1.50000
H2A3 2 0.512573 0.965928 0.196087 11.00000 -1.50000
AFIX 0
C3 1 0.638856 1.022327 0.271003 11.00000 0.01941 0.01694 =
0.01332 -0.00371 -0.00318 -0.00307
C3A 1 0.630991 1.111489 0.174401 11.00000 0.02748 0.02344 =
0.01557 0.00088 -0.00558 -0.00669
AFIX 137
H3A1 2 0.709863 1.107941 0.133891 11.00000 -1.50000
H3A2 2 0.601598 1.176094 0.185798 11.00000 -1.50000
H3A3 2 0.576357 1.108886 0.140182 11.00000 -1.50000
AFIX 0
C4 1 0.701759 1.009315 0.346833 11.00000 0.01730 0.01335 =
0.01449 -0.00484 -0.00188 -0.00327
C5 1 0.739100 1.091987 0.342410 11.00000 0.02219 0.01260 =
0.01675 -0.00315 -0.00250 -0.00540
AFIX 43
H5 2 0.733071 1.152518 0.284158 11.00000 -1.20000
AFIX 0
C6 1 0.782777 1.089418 0.416469 11.00000 0.01791 0.01321 =
0.01915 -0.00556 -0.00080 -0.00535
C7 1 0.802430 1.175575 0.425287 11.00000 0.01980 0.01394 =
0.02354 -0.00616 -0.00105 -0.00768
C7A 1 0.779429 1.282939 0.350069 11.00000 0.02630 0.01446 =
0.02802 -0.00398 -0.00174 -0.00927
AFIX 137
H7A1 2 0.787021 1.329479 0.375875 11.00000 -1.50000
H7A2 2 0.698972 1.304713 0.335111 11.00000 -1.50000
H7A3 2 0.837199 1.285091 0.289852 11.00000 -1.50000
AFIX 0
C8 1 0.840010 1.140137 0.512744 11.00000 0.02631 0.01731 =
0.02763 -0.00718 -0.00542 -0.01111
C8A 1 0.864285 1.199886 0.558405 11.00000 0.04531 0.02250 =
0.03595 -0.00666 -0.01504 -0.01864
AFIX 23
H8A1 2 0.888224 1.261110 0.505861 11.00000 -1.20000
H8A2 2 0.930828 1.156438 0.596012 11.00000 -1.20000
AFIX 0
C8B 1 0.755046 1.234434 0.627038 11.00000 0.07161 0.03547 =
0.03242 -0.01707 -0.00422 -0.02833
AFIX 137
H8B1 2 0.688915 1.276951 0.590010 11.00000 -1.50000
H8B2 2 0.772709 1.274798 0.654597 11.00000 -1.50000
H8B3 2 0.733256 1.173774 0.680647 11.00000 -1.50000
AFIX 0
C9 1 0.847662 1.030053 0.560941 11.00000 0.02573 0.01749 =
0.02451 -0.00590 -0.00757 -0.00989
C10 1 0.882954 0.962955 0.649324 11.00000 0.03624 0.02105 =
0.02874 -0.00465 -0.01531 -0.01326
AFIX 43
H10 2 0.900057 0.990685 0.687448 11.00000 -1.20000
AFIX 0
C11 1 0.896338 0.854177 0.689358 11.00000 0.02621 0.02002 =
0.02212 -0.00252 -0.01046 -0.01038
C12 1 0.928410 0.786780 0.787566 11.00000 0.03183 0.02518 =
0.02334 -0.00333 -0.01445 -0.01120
PART 1
C12A 1 0.935597 0.823352 0.862267 21.00000 0.05298 0.03212 =
0.03269 -0.00897 -0.02364 -0.01387
AFIX 23
H12A 2 0.968818 0.763244 0.918673 21.00000 -1.20000
H12B 2 0.989913 0.868565 0.832182 21.00000 -1.20000
AFIX 0
C12B 1 0.825172 0.876942 0.895862 21.00000 0.06952 0.05011 =
0.03130 -0.02394 -0.01383 -0.00045
AFIX 137
H12C 2 0.791242 0.935515 0.839948 21.00000 -1.50000
H12D 2 0.833438 0.902175 0.942195 21.00000 -1.50000
H12E 2 0.772632 0.831091 0.929235 21.00000 -1.50000
AFIX 0
PART 2
C12C 1 0.935597 0.823352 0.862267 -21.00000 0.05298 0.03212 =
0.03269 -0.00897 -0.02364 -0.01387
AFIX 23
H12F 2 0.869443 0.886136 0.859080 -21.00000 -1.20000
H12G 2 0.921188 0.769943 0.928362 -21.00000 -1.20000
AFIX 0
C12D 1 1.045070 0.847065 0.855051 -21.00000 0.02297 0.02959 =
0.01935 -0.00963 -0.00479 -0.01139
AFIX 137
H12H 2 1.111620 0.785052 0.861578 -21.00000 -1.50000
H12I 2 1.036642 0.870517 0.907779 -21.00000 -1.50000
H12J 2 1.060210 0.901497 0.790967 -21.00000 -1.50000
AFIX 0
PART 0
C13 1 0.941914 0.689383 0.796243 11.00000 0.02266 0.02245 =
0.01778 -0.00175 -0.00871 -0.00803
C13A 1 0.974113 0.590689 0.881433 11.00000 0.03477 0.02555 =
0.02086 -0.00029 -0.01295 -0.00766
AFIX 137
H13A 2 0.994607 0.604247 0.930966 11.00000 -1.50000
H13B 2 1.042363 0.542529 0.858620 11.00000 -1.50000
H13C 2 0.906501 0.560513 0.910629 11.00000 -1.50000
AFIX 0
C14 1 0.914703 0.698535 0.705387 11.00000 0.01724 0.01806 =
0.01632 -0.00182 -0.00498 -0.00648
C15 1 0.915798 0.617068 0.686416 11.00000 0.01656 0.01502 =
0.01613 -0.00147 -0.00388 -0.00355
AFIX 43
H15 2 0.945253 0.550619 0.733354 11.00000 -1.20000
AFIX 0
C16 1 0.878738 0.618763 0.605878 11.00000 0.01614 0.01241 =
0.01541 -0.00225 -0.00280 -0.00332
C17 1 0.872126 0.535672 0.589768 11.00000 0.01667 0.01207 =
0.01900 -0.00407 -0.00017 -0.00380
C17A 1 0.911328 0.423376 0.651471 11.00000 0.02385 0.01257 =
0.02545 -0.00183 -0.00379 -0.00428
AFIX 137
H17A 2 0.969442 0.412602 0.690243 11.00000 -1.50000
H17B 2 0.947699 0.383994 0.608579 11.00000 -1.50000
H17C 2 0.842494 0.400053 0.695967 11.00000 -1.50000
AFIX 0
C18 1 0.815916 0.576839 0.506708 11.00000 0.01703 0.01265 =
0.01770 -0.00642 0.00088 -0.00486
C18A 1 0.791083 0.515954 0.462491 11.00000 0.02437 0.01624 =
0.02681 -0.01171 -0.00076 -0.00666
AFIX 137
H18A 2 0.730931 0.560594 0.419650 11.00000 -1.50000
H18B 2 0.761796 0.458545 0.515175 11.00000 -1.50000
H18C 2 0.864267 0.488872 0.423705 11.00000 -1.50000
AFIX 0
C19 1 0.788496 0.684016 0.474321 11.00000 0.01647 0.01265 =
0.01382 -0.00491 -0.00143 -0.00427
C20 1 0.726444 0.762544 0.389419 11.00000 0.01711 0.01349 =
0.01269 -0.00567 -0.00107 -0.00497
AFIX 13
H20 2 0.674506 0.729769 0.380118 11.00000 -1.20000
AFIX 0
C25 1 0.536136 0.849110 0.483978 11.00000 0.01691 0.01540 =
0.01342 -0.00474 -0.00267 -0.00334
AFIX 23
H25A 2 0.485607 0.917497 0.484059 11.00000 -1.20000
H25B 2 0.488929 0.818466 0.467598 11.00000 -1.20000
AFIX 0
C27 1 0.562201 0.680721 0.635760 11.00000 0.01602 0.01503 =
0.01477 -0.00569 -0.00089 -0.00612
C28 1 0.593367 0.649104 0.726238 11.00000 0.01892 0.01723 =
0.01443 -0.00413 -0.00190 -0.00695
AFIX 43
H28 2 0.599433 0.582549 0.776936 11.00000 -1.20000
AFIX 0
C29 1 0.614790 0.734296 0.729861 11.00000 0.01877 0.01931 =
0.01429 -0.00719 -0.00088 -0.00711
C30 1 0.594950 0.815617 0.640396 11.00000 0.01911 0.01676 =
0.01492 -0.00749 -0.00132 -0.00584
AFIX 43
H30 2 0.602540 0.882727 0.622161 11.00000 -1.20000
AFIX 0
C31 1 0.531513 0.620499 0.597155 11.00000 0.01643 0.01792 =
0.01980 -0.00867 0.00037 -0.00746
O32 5 0.506494 0.649605 0.516299 11.00000 0.02624 0.02345 =
0.02124 -0.00996 -0.00528 -0.00913
O33 5 0.533713 0.525798 0.665895 11.00000 0.03666 0.01939 =
0.02477 -0.00493 -0.00591 -0.01618
C34 1 0.496244 0.461025 0.639287 11.00000 0.04014 0.02434 =
0.03889 -0.01147 -0.00662 -0.01892
AFIX 137
H34A 2 0.414084 0.493396 0.626870 11.00000 -1.50000
H34B 2 0.501281 0.393517 0.693300 11.00000 -1.50000
H34C 2 0.547968 0.452253 0.579654 11.00000 -1.50000
AFIX 0
C35 1 0.651114 0.739142 0.809242 11.00000 0.02250 0.02572 =
0.01622 -0.00926 -0.00157 -0.00954
AFIX 43
H35 2 0.665817 0.801634 0.798374 11.00000 -1.20000
AFIX 0
O36 5 0.664339 0.668828 0.889346 11.00000 0.03137 0.03324 =
0.01584 -0.00604 -0.00524 -0.01280
C38 1 0.825461 0.767036 0.213506 11.00000 0.02328 0.02412 =
0.01477 -0.00972 -0.00016 -0.01007
C39 1 0.917696 0.803306 0.146116 11.00000 0.03090 0.03855 =
0.01776 -0.01383 0.00403 -0.01860
AFIX 43
H39 2 0.944426 0.801185 0.082065 11.00000 -1.20000
AFIX 0
C40 1 0.965250 0.844198 0.189586 11.00000 0.02391 0.02766 =
0.02020 -0.00985 0.00179 -0.01333
C41 1 0.900647 0.830537 0.283244 11.00000 0.01782 0.01669 =
0.01817 -0.00767 -0.00186 -0.00548
AFIX 43
H41 2 0.914273 0.849641 0.329914 11.00000 -1.20000
AFIX 0
C42 1 0.752899 0.714180 0.202730 11.00000 0.02741 0.02486 =
0.01801 -0.01134 -0.00233 -0.01010
O43 5 0.666613 0.689918 0.258443 11.00000 0.03254 0.03626 =
0.02510 -0.01753 0.00274 -0.02001
O44 5 0.796138 0.694033 0.120465 11.00000 0.04711 0.07318 =
0.03067 -0.03677 0.01066 -0.03585
C45 1 0.730033 0.643552 0.101484 11.00000 0.05390 0.08009 =
0.04716 -0.04771 0.00453 -0.03456
AFIX 137
H45A 2 0.729255 0.576880 0.155724 11.00000 -1.50000
H45B 2 0.767485 0.632668 0.039718 11.00000 -1.50000
H45C 2 0.648370 0.686752 0.096093 11.00000 -1.50000
AFIX 0
PART 1
C46A 1 1.062999 0.892082 0.145814 31.00000 0.03559 0.05516 =
0.02966 -0.01973 0.00904 -0.03065
AFIX 43
H46A 2 1.096502 0.902360 0.078908 31.00000 -1.20000
AFIX 0
O47A 5 1.104624 0.919955 0.190502 31.00000 0.03961 0.04068 =
0.03312 -0.01518 0.00199 -0.02554
PART 2
C46B 1 1.062999 0.892082 0.145814 -31.00000 0.03559 0.05516 =
0.02966 -0.01973 0.00904 -0.03065
AFIX 43
H46B 2 1.104728 0.894715 0.187863 -31.00000 -1.20000
AFIX 0
O47B 5 1.095072 0.931309 0.051253 -31.00000 0.06474 0.10778 =
0.02499 -0.01437 0.01022 -0.06860
PART 0
H22 2 0.810517 0.947241 0.509319 11.00000 0.03590
H24 2 0.820245 0.766479 0.529276 11.00000 0.02254
MOLE 2
PART 2
C1S 1 0.304587 0.571463 0.016594 11.00000 0.04235 0.03327 =
0.03292 0.00035 -0.00901 -0.01682
AFIX 13
H1S 2 0.324890 0.494809 0.051366 11.00000 -1.20000
AFIX 0
CL1 3 0.167188 0.624958 0.075278 11.00000 0.06855 0.05025 =
0.04723 -0.01530 0.01524 -0.01863
CL2 3 0.297926 0.601669 -0.106151 11.00000 0.08363 0.06325 =
0.03089 -0.00836 -0.00688 -0.02031
CL3 3 0.416641 0.616205 0.019796 11.00000 0.07400 0.05215 =
0.12673 0.01094 -0.06000 -0.03167
HKLF 4
REM gmf13036
REM R1 = 0.0542 for 12861 Fo > 4sig(Fo) and 0.0621 for all 15250 data
REM 589 parameters refined using 1 restraints
END
WGHT 0.0821 1.1312
REM Highest difference peak 0.931, deepest hole -1.097, 1-sigma level 0.065
Q1 1 0.2350 0.6338 -0.1068 11.00000 0.05 0.93
Q2 1 0.2060 0.6000 0.1197 11.00000 0.05 0.80
Q3 1 0.3583 0.6415 0.0415 11.00000 0.05 0.79
Q4 1 0.3347 0.6189 -0.0932 11.00000 0.05 0.66
Q5 1 0.4230 0.6094 -0.0145 11.00000 0.05 0.56
Q6 1 0.7605 1.0901 0.3794 11.00000 0.05 0.53
Q7 1 0.5717 0.6624 0.6783 11.00000 0.05 0.51
Q8 1 0.6741 1.0182 0.3014 11.00000 0.05 0.49
Q9 1 0.9002 0.6192 0.6431 11.00000 0.05 0.47
Q10 1 0.8431 0.5528 0.5493 11.00000 0.05 0.47
Q11 1 0.5398 0.6515 0.6161 11.00000 0.05 0.46
Q12 1 0.6308 0.7315 0.7651 11.00000 0.05 0.46
Q13 1 0.7992 1.1367 0.4125 11.00000 0.05 0.46
Q14 1 0.8231 1.1589 0.4677 11.00000 0.05 0.45
Q15 1 0.5759 0.8014 0.6074 11.00000 0.05 0.44
Q16 1 0.7941 0.7347 0.2100 11.00000 0.05 0.44
Q17 1 0.9300 0.6902 0.7500 11.00000 0.05 0.44
Q18 1 0.8775 0.7815 0.1794 11.00000 0.05 0.44
Q19 1 0.2913 0.5488 -0.0829 11.00000 0.05 0.43
Q20 1 0.6226 0.9032 0.3519 11.00000 0.05 0.43
;
# start Validation Reply Form
_vrf_PLAT601_I
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of . 183 Ang3
RESPONSE: All significant residual electron dnsity is near assigned atoms. The
VOID lacks electron density. (It was not removed with, for example, SQUEEZE.
;
# end Validation Reply Form
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./
# END of CIF
_database_code_depnum_ccdc_archive 'CCDC 941797'