# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal SOciety of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'David Dolphin'
_publ_contact_author_email       DAVID.DOLPHIN@QLTINC.COM

_publ_section_title              
;
Conformational Flexibility of Dipyrromethenes:
Supramolecular Assemblies with Hydroquinones
;
loop_
_publ_author_name
'D Dolphin'
"Brian O'Patrick"
'Ji-Young Shin.'

# Attachment 'CIFs.txt'

data_Compound1
_database_code_depnum_ccdc_archive 'CCDC 673445'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 N3 O2'
_chemical_formula_weight         265.27

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.6809(16)
_cell_length_b                   7.4146(9)
_cell_length_c                   24.350(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2650.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6096
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      23.97

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   ?

_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  'Bruker X8 APEX'
_diffrn_measurement_method       'area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            54647
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         27.85
_reflns_number_total             3122
_reflns_number_gt                2243
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0512P)²+0.5503P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3122
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.34074(10) 0.2034(2) 0.13516(6) 0.0519(4) Uani 1 1 d . . .
H1 H 0.3071 0.0973 0.1434 0.062 Uiso 1 1 calc R . .
C2 C 0.31679(11) 0.3320(2) 0.09683(6) 0.0536(4) Uani 1 1 d . . .
H2 H 0.2641 0.3302 0.0742 0.064 Uiso 1 1 calc R . .
C3 C 0.38429(10) 0.4659(2) 0.09730(5) 0.0477(3) Uani 1 1 d . . .
H3 H 0.3855 0.5715 0.0752 0.057 Uiso 1 1 calc R . .
C4 C 0.44968(9) 0.41526(17) 0.13644(5) 0.0391(3) Uani 1 1 d . . .
C5 C 0.53293(9) 0.50252(16) 0.15289(5) 0.0368(3) Uani 1 1 d . . .
C6 C 0.58779(9) 0.44213(17) 0.19552(5) 0.0380(3) Uani 1 1 d . . .
C7 C 0.67783(10) 0.50415(18) 0.21050(5) 0.0435(3) Uani 1 1 d . . .
H7 H 0.7109 0.5998 0.1939 0.052 Uiso 1 1 calc R . .
C8 C 0.70580(10) 0.3988(2) 0.25291(6) 0.0498(4) Uani 1 1 d . . .
H8 H 0.7624 0.4057 0.2717 0.060 Uiso 1 1 calc R . .
C9 C 0.63284(11) 0.2748(2) 0.26370(5) 0.0504(4) Uani 1 1 d . . .
H9 H 0.6346 0.1865 0.2920 0.060 Uiso 1 1 calc R . .
C10 C 0.56087(9) 0.66819(17) 0.12200(5) 0.0378(3) Uani 1 1 d . . .
C11 C 0.57832(9) 0.82897(17) 0.15038(5) 0.0427(3) Uani 1 1 d . . .
H11 H 0.5713 0.8324 0.1891 0.051 Uiso 1 1 calc R . .
C12 C 0.60580(10) 0.98379(18) 0.12253(6) 0.0496(4) Uani 1 1 d . . .
H12 H 0.6188 1.0921 0.1418 0.059 Uiso 1 1 calc R . .
C13 C 0.61371(10) 0.9754(2) 0.06582(6) 0.0516(4) Uani 1 1 d . . .
C14 C 0.59651(11) 0.8195(2) 0.03618(6) 0.0537(4) Uani 1 1 d . . .
H14 H 0.6025 0.8182 -0.0027 0.064 Uiso 1 1 calc R . .
C15 C 0.57040(10) 0.6653(2) 0.06443(5) 0.0465(3) Uani 1 1 d . . .
H15 H 0.5589 0.5569 0.0448 0.056 Uiso 1 1 calc R . .
N1 N 0.42022(8) 0.25340(16) 0.15914(5) 0.0448(3) Uani 1 1 d . . .
N2 N 0.56307(8) 0.29641(15) 0.23023(4) 0.0451(3) Uani 1 1 d . . .
N3 N 0.64200(11) 1.1402(2) 0.03623(8) 0.0759(5) Uani 1 1 d . . .
O1 O 0.67250(13) 1.2687(2) 0.06305(8) 0.1067(6) Uani 1 1 d . . .
O2 O 0.63308(11) 1.1408(2) -0.01446(7) 0.1018(6) Uani 1 1 d . . .
H1N H 0.4498(12) 0.199(2) 0.1880(7) 0.068(5) Uiso 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.357(2) . ?
C1 C2 1.380(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.403(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.4039(19) . ?
C3 H3 0.9500 . ?
C4 N1 1.3903(17) . ?
C4 C5 1.4397(19) . ?
C5 C6 1.3882(18) . ?
C5 C10 1.4977(17) . ?
C6 N2 1.4190(16) . ?
C6 C7 1.446(2) . ?
C7 C8 1.3585(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.436(2) . ?
C8 H8 0.9500 . ?
C9 N2 1.3186(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.4015(18) . ?
C10 C15 1.4090(18) . ?
C11 C12 1.3930(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 N3 1.4781(19) . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N1 H1N 0.920(18) . ?
N3 O1 1.239(2) . ?
N3 O2 1.241(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 C1 C2 108.74(13) . . ?
N1 C1 H1 125.6 . . ?
C2 C1 H1 125.6 . . ?
C1 C2 C3 107.68(13) . . ?
C1 C2 H2 126.2 . . ?
C3 C2 H2 126.2 . . ?
C2 C3 C4 107.41(13) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
N1 C4 C3 106.75(12) . . ?
N1 C4 C5 122.78(12) . . ?
C3 C4 C5 130.47(12) . . ?
C6 C5 C4 123.76(12) . . ?
C6 C5 C10 118.76(12) . . ?
C4 C5 C10 117.48(11) . . ?
C5 C6 N2 122.86(12) . . ?
C5 C6 C7 128.05(12) . . ?
N2 C6 C7 109.01(11) . . ?
C8 C7 C6 106.56(12) . . ?
C8 C7 H7 126.7 . . ?
C6 C7 H7 126.7 . . ?
C7 C8 C9 106.37(13) . . ?
C7 C8 H8 126.8 . . ?
C9 C8 H8 126.8 . . ?
N2 C9 C8 112.86(12) . . ?
N2 C9 H9 123.6 . . ?
C8 C9 H9 123.6 . . ?
C11 C10 C15 119.05(12) . . ?
C11 C10 C5 120.01(10) . . ?
C15 C10 C5 120.95(12) . . ?
C12 C11 C10 120.92(12) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 118.16(13) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C14 C13 C12 122.73(13) . . ?
C14 C13 N3 119.12(14) . . ?
C12 C13 N3 118.15(15) . . ?
C13 C14 C15 118.63(13) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C14 C15 C10 120.50(13) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C1 N1 C4 109.41(12) . . ?
C1 N1 H1N 127.8(11) . . ?
C4 N1 H1N 122.6(11) . . ?
C9 N2 C6 105.19(12) . . ?
O1 N3 O2 124.02(16) . . ?
O1 N3 C13 118.70(17) . . ?
O2 N3 C13 117.28(19) . . ?

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
N1 C1 C2 C3 0.07(16) . . . . ?
C1 C2 C3 C4 0.30(16) . . . . ?
C2 C3 C4 N1 -0.55(15) . . . . ?
C2 C3 C4 C5 179.24(13) . . . . ?
N1 C4 C5 C6 -5.23(19) . . . . ?
C3 C4 C5 C6 175.02(13) . . . . ?
N1 C4 C5 C10 175.02(11) . . . . ?
C3 C4 C5 C10 -4.73(19) . . . . ?
C4 C5 C6 N2 -5.49(19) . . . . ?
C10 C5 C6 N2 174.25(10) . . . . ?
C4 C5 C6 C7 170.87(12) . . . . ?
C10 C5 C6 C7 -9.38(19) . . . . ?
C5 C6 C7 C8 -176.88(13) . . . . ?
N2 C6 C7 C8 -0.11(14) . . . . ?
C6 C7 C8 C9 -0.39(15) . . . . ?
C7 C8 C9 N2 0.82(17) . . . . ?
C6 C5 C10 C11 -54.47(17) . . . . ?
C4 C5 C10 C11 125.29(13) . . . . ?
C6 C5 C10 C15 125.26(13) . . . . ?
C4 C5 C10 C15 -54.98(16) . . . . ?
C15 C10 C11 C12 -0.8(2) . . . . ?
C5 C10 C11 C12 178.96(12) . . . . ?
C10 C11 C12 C13 1.2(2) . . . . ?
C11 C12 C13 C14 -0.8(2) . . . . ?
C11 C12 C13 N3 179.42(13) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
N3 C13 C14 C15 179.69(14) . . . . ?
C13 C14 C15 C10 0.6(2) . . . . ?
C11 C10 C15 C14 -0.2(2) . . . . ?
C5 C10 C15 C14 -179.88(13) . . . . ?
C2 C1 N1 C4 -0.42(15) . . . . ?
C3 C4 N1 C1 0.60(14) . . . . ?
C5 C4 N1 C1 -179.20(12) . . . . ?
C8 C9 N2 C6 -0.86(16) . . . . ?
C5 C6 N2 C9 177.57(12) . . . . ?
C7 C6 N2 C9 0.59(14) . . . . ?
C14 C13 N3 O1 -167.49(16) . . . . ?
C12 C13 N3 O1 12.3(2) . . . . ?
C14 C13 N3 O2 12.8(2) . . . . ?
C12 C13 N3 O2 -167.37(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.85
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.032

#===End
data_compound2
_database_code_depnum_ccdc_archive 'CCDC 673446'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H13 Cl2 N5 O4'
_chemical_formula_weight         494.28

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.508(2)
_cell_length_b                   19.587(3)
_cell_length_c                   11.039(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.970(10)
_cell_angle_gamma                90.00
_cell_volume                     2161.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4965
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      22.98

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   ?

_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  'Bruker X8 APEX'
_diffrn_measurement_method       'area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            34997
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         25.15
_reflns_number_total             3842
_reflns_number_gt                2752
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² 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/[σ²(Fo²)+(0.0702P)²+0.4140P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3842
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1290
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9359(3) 0.08992(13) 0.5275(2) 0.0226(6) Uani 1 1 d . . .
C2 C 0.9642(3) 0.06700(13) 0.6539(2) 0.0241(6) Uani 1 1 d . . .
C3 C 0.8954(3) 0.01659(14) 0.7017(3) 0.0280(6) Uani 1 1 d . . .
H3 H 0.8162 -0.0064 0.6542 0.034 Uiso 1 1 calc R . .
C4 C 0.9635(3) 0.00661(16) 0.8292(3) 0.0358(7) Uani 1 1 d . . .
H4 H 0.9409 -0.0248 0.8849 0.043 Uiso 1 1 calc R . .
C5 C 1.0714(3) 0.05141(16) 0.8602(3) 0.0343(7) Uani 1 1 d . . .
H5 H 1.1346 0.0561 0.9425 0.041 Uiso 1 1 calc R . .
C6 C 1.0299(3) 0.12280(13) 0.4789(2) 0.0238(6) Uani 1 1 d . . .
C7 C 1.1704(3) 0.12706(13) 0.5249(3) 0.0263(6) Uani 1 1 d . . .
H7 H 1.2258 0.1093 0.6036 0.032 Uiso 1 1 calc R . .
C8 C 1.2137(3) 0.16152(15) 0.4357(3) 0.0342(7) Uani 1 1 d . . .
H8 H 1.3039 0.1715 0.4417 0.041 Uiso 1 1 calc R . .
C9 C 1.1009(3) 0.17892(14) 0.3355(3) 0.0351(7) Uani 1 1 d . . .
H9 H 1.1012 0.2032 0.2611 0.042 Uiso 1 1 calc R . .
C10 C 0.7995(3) 0.07586(13) 0.4401(2) 0.0234(6) Uani 1 1 d . . .
C11 C 0.7820(3) 0.04906(13) 0.3180(2) 0.0247(6) Uani 1 1 d . . .
H11 H 0.8583 0.0393 0.2921 0.030 Uiso 1 1 calc R . .
C12 C 0.6558(3) 0.03677(14) 0.2352(3) 0.0279(6) Uani 1 1 d . . .
H12 H 0.6439 0.0181 0.1530 0.034 Uiso 1 1 calc R . .
C13 C 0.5469(3) 0.05257(14) 0.2759(3) 0.0278(6) Uani 1 1 d . . .
C14 C 0.5599(3) 0.07817(14) 0.3958(3) 0.0315(7) Uani 1 1 d . . .
H14 H 0.4832 0.0877 0.4211 0.038 Uiso 1 1 calc R . .
C15 C 0.6869(3) 0.08959(14) 0.4780(3) 0.0300(7) Uani 1 1 d . . .
H15 H 0.6977 0.1069 0.5609 0.036 Uiso 1 1 calc R . .
C16 C 0.4899(3) 0.21268(14) 1.1351(2) 0.0283(7) Uani 1 1 d . . .
C17 C 0.6192(3) 0.19838(13) 1.1296(3) 0.0287(7) Uani 1 1 d . . .
C18 C 0.6314(3) 0.17126(13) 1.0165(3) 0.0277(6) Uani 1 1 d . . .
C19 C 0.5172(3) 0.16100(13) 0.9093(3) 0.0262(6) Uani 1 1 d . . .
C20 C 0.3879(3) 0.17761(13) 0.9130(2) 0.0258(6) Uani 1 1 d . . .
C21 C 0.3776(3) 0.20157(13) 1.0303(3) 0.0270(6) Uani 1 1 d . . .
C22 C 0.7657(3) 0.15692(16) 1.0098(3) 0.0361(7) Uani 1 1 d . . .
C23 C 0.5298(3) 0.13652(15) 0.7889(3) 0.0319(7) Uani 1 1 d . . .
N1 N 1.0730(2) 0.08697(12) 0.7570(2) 0.0263(5) Uani 1 1 d . . .
N2 N 0.9921(3) 0.15597(11) 0.3607(2) 0.0278(6) Uani 1 1 d . . .
N3 N 0.4112(2) 0.04401(13) 0.1843(2) 0.0338(6) Uani 1 1 d . . .
N4 N 0.5360(3) 0.11839(16) 0.6964(3) 0.0547(8) Uani 1 1 d . . .
N5 N 0.8690(3) 0.14867(18) 1.0080(3) 0.0630(9) Uani 1 1 d . . .
O1 O 0.3168(2) 0.06687(12) 0.2148(2) 0.0479(6) Uani 1 1 d . . .
O2 O 0.4000(2) 0.01673(13) 0.0823(2) 0.0517(6) Uani 1 1 d . . .
O3 O 0.72965(19) 0.20807(10) 1.22953(18) 0.0351(5) Uani 1 1 d . . .
O4 O 0.28355(18) 0.17350(9) 0.80962(17) 0.0300(5) Uani 1 1 d . . .
Cl1 Cl 0.47159(8) 0.24573(4) 1.27419(7) 0.0392(2) Uani 1 1 d . . .
Cl2 Cl 0.21988(7) 0.21811(5) 1.04038(7) 0.0430(2) Uani 1 1 d . . .
H3A H 0.739(5) 0.255(2) 1.259(5) 0.109(17) Uiso 1 1 d . . .
H2 H 0.907(3) 0.1623(16) 0.311(3) 0.044(10) Uiso 1 1 d . . .
H1 H 1.133(3) 0.1186(15) 0.760(3) 0.032(8) Uiso 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.407(4) . ?
C1 C6 1.416(4) . ?
C1 C10 1.486(4) . ?
C2 N1 1.398(3) . ?
C2 C3 1.418(4) . ?
C3 C4 1.382(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(4) . ?
C4 H4 0.9500 . ?
C5 N1 1.340(4) . ?
C5 H5 0.9500 . ?
C6 N2 1.400(3) . ?
C6 C7 1.408(4) . ?
C7 C8 1.381(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(4) . ?
C8 H8 0.9500 . ?
C9 N2 1.335(4) . ?
C9 H9 0.9500 . ?
C10 C15 1.398(4) . ?
C10 C11 1.405(4) . ?
C11 C12 1.380(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(4) . ?
C13 N3 1.481(4) . ?
C14 C15 1.381(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.391(4) . ?
C16 C17 1.407(4) . ?
C16 Cl1 1.731(3) . ?
C17 O3 1.346(3) . ?
C17 C18 1.399(4) . ?
C18 C19 1.416(4) . ?
C18 C22 1.463(5) . ?
C19 C20 1.409(4) . ?
C19 C23 1.458(4) . ?
C20 O4 1.319(3) . ?
C20 C21 1.413(4) . ?
C21 Cl2 1.725(3) . ?
C22 N5 1.103(4) . ?
C23 N4 1.102(4) . ?
N1 H1 0.88(3) . ?
N2 H2 0.90(3) . ?
N3 O2 1.219(3) . ?
N3 O1 1.227(3) . ?
O3 H3A 0.97(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 124.2(2) . . ?
C2 C1 C10 116.8(2) . . ?
C6 C1 C10 119.0(2) . . ?
N1 C2 C1 126.0(2) . . ?
N1 C2 C3 105.9(2) . . ?
C1 C2 C3 128.0(2) . . ?
C4 C3 C2 108.3(2) . . ?
C4 C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
C3 C4 C5 106.7(3) . . ?
C3 C4 H4 126.6 . . ?
C5 C4 H4 126.6 . . ?
N1 C5 C4 110.0(2) . . ?
N1 C5 H5 125.0 . . ?
C4 C5 H5 125.0 . . ?
N2 C6 C7 105.9(2) . . ?
N2 C6 C1 122.2(2) . . ?
C7 C6 C1 131.8(2) . . ?
C8 C7 C6 108.1(2) . . ?
C8 C7 H7 125.9 . . ?
C6 C7 H7 125.9 . . ?
C7 C8 C9 107.4(3) . . ?
C7 C8 H8 126.3 . . ?
C9 C8 H8 126.3 . . ?
N2 C9 C8 109.0(3) . . ?
N2 C9 H9 125.5 . . ?
C8 C9 H9 125.5 . . ?
C15 C10 C11 119.1(2) . . ?
C15 C10 C1 120.5(2) . . ?
C11 C10 C1 120.4(2) . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 117.8(3) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C14 C13 C12 122.9(3) . . ?
C14 C13 N3 119.0(3) . . ?
C12 C13 N3 118.0(2) . . ?
C15 C14 C13 118.6(3) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C10 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C21 C16 C17 121.1(3) . . ?
C21 C16 Cl1 119.9(2) . . ?
C17 C16 Cl1 119.1(2) . . ?
O3 C17 C18 119.5(3) . . ?
O3 C17 C16 122.5(3) . . ?
C18 C17 C16 118.0(2) . . ?
C17 C18 C19 120.8(3) . . ?
C17 C18 C22 118.3(2) . . ?
C19 C18 C22 120.9(3) . . ?
C20 C19 C18 121.3(3) . . ?
C20 C19 C23 117.5(2) . . ?
C18 C19 C23 121.1(2) . . ?
O4 C20 C19 120.9(2) . . ?
O4 C20 C21 122.3(2) . . ?
C19 C20 C21 116.8(2) . . ?
C16 C21 C20 121.9(3) . . ?
C16 C21 Cl2 120.1(2) . . ?
C20 C21 Cl2 118.0(2) . . ?
N5 C22 C18 176.8(4) . . ?
N4 C23 C19 178.2(3) . . ?
C5 N1 C2 109.0(2) . . ?
C5 N1 H1 122.4(19) . . ?
C2 N1 H1 128.6(19) . . ?
C9 N2 C6 109.6(3) . . ?
C9 N2 H2 125(2) . . ?
C6 N2 H2 125(2) . . ?
O2 N3 O1 123.9(2) . . ?
O2 N3 C13 118.6(2) . . ?
O1 N3 C13 117.4(2) . . ?
C17 O3 H3A 112(3) . . ?

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
C6 C1 C2 N1 16.9(4) . . . . ?
C10 C1 C2 N1 -165.4(2) . . . . ?
C6 C1 C2 C3 -158.6(3) . . . . ?
C10 C1 C2 C3 19.1(4) . . . . ?
N1 C2 C3 C4 -0.8(3) . . . . ?
C1 C2 C3 C4 175.4(3) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 N1 -1.2(4) . . . . ?
C2 C1 C6 N2 -167.8(2) . . . . ?
C10 C1 C6 N2 14.5(4) . . . . ?
C2 C1 C6 C7 16.6(4) . . . . ?
C10 C1 C6 C7 -161.0(3) . . . . ?
N2 C6 C7 C8 -0.3(3) . . . . ?
C1 C6 C7 C8 175.8(3) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C7 C8 C9 N2 -0.3(3) . . . . ?
C2 C1 C10 C15 47.1(3) . . . . ?
C6 C1 C10 C15 -135.1(3) . . . . ?
C2 C1 C10 C11 -133.4(3) . . . . ?
C6 C1 C10 C11 44.4(3) . . . . ?
C15 C10 C11 C12 0.5(4) . . . . ?
C1 C10 C11 C12 -179.0(2) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C12 C13 C14 -1.7(4) . . . . ?
C11 C12 C13 N3 175.8(2) . . . . ?
C12 C13 C14 C15 1.1(4) . . . . ?
N3 C13 C14 C15 -176.4(2) . . . . ?
C13 C14 C15 C10 0.3(4) . . . . ?
C11 C10 C15 C14 -1.1(4) . . . . ?
C1 C10 C15 C14 178.4(2) . . . . ?
C21 C16 C17 O3 -179.5(2) . . . . ?
Cl1 C16 C17 O3 1.4(4) . . . . ?
C21 C16 C17 C18 -1.3(4) . . . . ?
Cl1 C16 C17 C18 179.6(2) . . . . ?
O3 C17 C18 C19 -179.5(2) . . . . ?
C16 C17 C18 C19 2.3(4) . . . . ?
O3 C17 C18 C22 -2.4(4) . . . . ?
C16 C17 C18 C22 179.4(2) . . . . ?
C17 C18 C19 C20 -0.1(4) . . . . ?
C22 C18 C19 C20 -177.0(3) . . . . ?
C17 C18 C19 C23 176.4(3) . . . . ?
C22 C18 C19 C23 -0.6(4) . . . . ?
C18 C19 C20 O4 174.0(2) . . . . ?
C23 C19 C20 O4 -2.5(4) . . . . ?
C18 C19 C20 C21 -3.1(4) . . . . ?
C23 C19 C20 C21 -179.7(2) . . . . ?
C17 C16 C21 C20 -2.0(4) . . . . ?
Cl1 C16 C21 C20 177.1(2) . . . . ?
C17 C16 C21 Cl2 178.8(2) . . . . ?
Cl1 C16 C21 Cl2 -2.1(3) . . . . ?
O4 C20 C21 C16 -173.0(2) . . . . ?
C19 C20 C21 C16 4.2(4) . . . . ?
O4 C20 C21 Cl2 6.2(4) . . . . ?
C19 C20 C21 Cl2 -176.67(19) . . . . ?
C17 C18 C22 N5 -35(7) . . . . ?
C19 C18 C22 N5 142(6) . . . . ?
C20 C19 C23 N4 7(11) . . . . ?
C18 C19 C23 N4 -169(100) . . . . ?
C4 C5 N1 C2 0.7(3) . . . . ?
C1 C2 N1 C5 -176.2(3) . . . . ?
C3 C2 N1 C5 0.1(3) . . . . ?
C8 C9 N2 C6 0.2(3) . . . . ?
C7 C6 N2 C9 0.1(3) . . . . ?
C1 C6 N2 C9 -176.5(2) . . . . ?
C14 C13 N3 O2 -174.6(3) . . . . ?
C12 C13 N3 O2 7.8(4) . . . . ?
C14 C13 N3 O1 7.5(4) . . . . ?
C12 C13 N3 O1 -170.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.15
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.081


