# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2005

data_global

_journal_coden_Cambridge         182
_journal_volume                  ?
_journal_year                    ?
_journal_page_first              ?

_publ_requested_journal          'Chemical Communications'

loop_
_publ_author_name
'Graeme Cooke'
'Alan S. F. Boyd'
'Josepth B. Carroll'
'James F Garety'
B.J.Jordan
'Suhil Mabruk'
'Georgina Rosair'
V.M.Rotello

_publ_contact_author_name        'Graeme Cooke'
_publ_contact_author_address     
;
Centre for Biomimetic Design & Synthesis
Heriot-Watt University
William H Perkin Building
School of Engineering
Riccarton
Edinburgh
EH14 4AS
UNITED KINGDOM
;

_publ_contact_author_email       G.COOKE@HW.AC.UK

_publ_section_title              
;Model systems for flavoenzyme activity: anelectrochemically
tuneable intramolecularly hydrogen bonded flavin-diamidopyridine complex
;

data_x80314
_database_code_depnum_ccdc_archive 'CCDC 259130'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H43 N7 O6, Cl2 C H2'
_chemical_formula_sum            'C35 H45 Cl2 N7 O6'
_chemical_formula_weight         730.68

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1226(12)
_cell_length_b                   13.640(2)
_cell_length_c                   15.435(2)
_cell_angle_alpha                71.272(4)
_cell_angle_beta                 76.201(6)
_cell_angle_gamma                81.735(4)
_cell_volume                     1761.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1189
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      25.33

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             772
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            51896
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         28.00
_reflns_number_total             8351
_reflns_number_gt                5710
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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^)+(0.1000P)^2^+0.4825P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8351
_refine_ls_number_parameters     468
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1754
_refine_ls_wR_factor_gt          0.1479
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
N1 N 0.71356(18) -0.11074(12) 1.06868(11) 0.0175(4) Uani 1 1 d . . .
C2 C 0.6359(2) -0.14085(15) 1.01572(14) 0.0175(4) Uani 1 1 d . . .
C3 C 0.5678(2) -0.23538(15) 1.04649(14) 0.0198(4) Uani 1 1 d . . .
H3 H 0.5707 -0.2806 1.1075 0.024 Uiso 1 1 calc R . .
C4 C 0.4969(2) -0.26357(15) 0.98988(15) 0.0213(4) Uani 1 1 d . . .
C5 C 0.4880(2) -0.19584(16) 0.89907(15) 0.0208(4) Uani 1 1 d . . .
C6 C 0.5523(2) -0.10278(15) 0.86883(14) 0.0195(4) Uani 1 1 d . . .
H6 H 0.5474 -0.0576 0.8081 0.023 Uiso 1 1 calc R . .
C7 C 0.6256(2) -0.07249(15) 0.92585(14) 0.0179(4) Uani 1 1 d . . .
N8 N 0.68317(18) 0.02256(13) 0.89217(12) 0.0183(4) Uani 1 1 d . . .
C9 C 0.7511(2) 0.04862(15) 0.94573(13) 0.0163(4) Uani 1 1 d . . .
C10 C 0.8143(2) 0.15201(14) 0.91144(14) 0.0173(4) Uani 1 1 d . . .
O10 O 0.80603(17) 0.21518(11) 0.83549(10) 0.0233(3) Uani 1 1 d . . .
H11 H 0.915(3) 0.231(2) 0.9583(19) 0.037(7) Uiso 1 1 d . . .
N11 N 0.88322(19) 0.17130(13) 0.97249(12) 0.0188(4) Uani 1 1 d . . .
C12 C 0.9069(2) 0.10149(15) 1.05776(14) 0.0179(4) Uani 1 1 d . . .
O12 O 0.98099(17) 0.12860(11) 1.10172(10) 0.0239(3) Uani 1 1 d . . .
N13 N 0.84884(19) 0.00693(13) 1.08950(12) 0.0186(4) Uani 1 1 d . . .
C14 C 0.7733(2) -0.01625(15) 1.03647(14) 0.0171(4) Uani 1 1 d . . .
C15 C 0.7408(2) -0.18055(15) 1.16012(14) 0.0198(4) Uani 1 1 d . . .
H15A H 0.8460 -0.1757 1.1643 0.024 Uiso 1 1 calc R . .
H15B H 0.7307 -0.2530 1.1634 0.024 Uiso 1 1 calc R . .
C16 C 0.6330(2) -0.15569(16) 1.24338(14) 0.0208(4) Uani 1 1 d . . .
H16A H 0.5290 -0.1704 1.2451 0.025 Uiso 1 1 calc R . .
H16B H 0.6327 -0.0810 1.2368 0.025 Uiso 1 1 calc R . .
C17 C 0.6813(2) -0.22070(17) 1.33422(15) 0.0242(5) Uani 1 1 d . . .
H17A H 0.6845 -0.2950 1.3387 0.029 Uiso 1 1 calc R . .
H17B H 0.6034 -0.2087 1.3874 0.029 Uiso 1 1 calc R . .
C18 C 0.8351(2) -0.19796(16) 1.34386(15) 0.0237(5) Uani 1 1 d . . .
H18A H 0.8604 -0.2480 1.4018 0.028 Uiso 1 1 calc R . .
H18B H 0.9129 -0.2099 1.2906 0.028 Uiso 1 1 calc R . .
C19 C 0.8440(2) -0.08855(17) 1.34694(16) 0.0252(5) Uani 1 1 d . . .
H19A H 0.8168 -0.0375 1.2900 0.030 Uiso 1 1 calc R . .
H19B H 0.7703 -0.0767 1.4018 0.030 Uiso 1 1 calc R . .
C20 C 1.0009(2) -0.07229(17) 1.35301(16) 0.0254(5) Uani 1 1 d . . .
H20A H 1.0364 -0.1296 1.4035 0.031 Uiso 1 1 calc R . .
H20B H 1.0727 -0.0703 1.2933 0.031 Uiso 1 1 calc R . .
O20 O 0.99214(16) 0.02563(12) 1.37251(11) 0.0261(3) Uani 1 1 d . . .
C21 C 1.1231(2) 0.05813(18) 1.37406(14) 0.0251(5) Uani 1 1 d . . .
O21 O 1.24283(18) 0.00827(13) 1.36343(12) 0.0328(4) Uani 1 1 d . . .
C22 C 1.1022(3) 0.16458(17) 1.38679(15) 0.0259(5) Uani 1 1 d . . .
H22A H 1.1550 0.1645 1.4359 0.031 Uiso 1 1 calc R . .
H22B H 0.9932 0.1827 1.4074 0.031 Uiso 1 1 calc R . .
C23 C 1.1654(2) 0.24565(17) 1.29516(15) 0.0244(5) Uani 1 1 d . . .
H23A H 1.1475 0.3152 1.3046 0.029 Uiso 1 1 calc R . .
H23B H 1.2762 0.2307 1.2780 0.029 Uiso 1 1 calc R . .
C24 C 1.0941(2) 0.24708(16) 1.21577(15) 0.0232(4) Uani 1 1 d . . .
H24A H 0.9826 0.2557 1.2353 0.028 Uiso 1 1 calc R . .
H24B H 1.1198 0.1795 1.2027 0.028 Uiso 1 1 calc R . .
C25 C 1.1454(2) 0.33308(16) 1.12697(15) 0.0212(4) Uani 1 1 d . . .
O25 O 1.22565(17) 0.39869(12) 1.12302(11) 0.0267(3) Uani 1 1 d . . .
H26 H 1.043(3) 0.270(2) 1.0648(18) 0.030(7) Uiso 1 1 d . . .
N26 N 1.0906(2) 0.32819(13) 1.05291(12) 0.0199(4) Uani 1 1 d . . .
C27 C 1.1108(2) 0.39645(15) 0.96207(14) 0.0181(4) Uani 1 1 d . . .
C28 C 1.2013(2) 0.47984(16) 0.93229(15) 0.0219(4) Uani 1 1 d . . .
H28 H 1.2502 0.4951 0.9739 0.026 Uiso 1 1 calc R . .
C29 C 1.2171(2) 0.53935(16) 0.84002(15) 0.0237(5) Uani 1 1 d . . .
H29 H 1.2792 0.5962 0.8172 0.028 Uiso 1 1 calc R . .
C30 C 1.1444(2) 0.51781(16) 0.78048(15) 0.0230(4) Uani 1 1 d . . .
H30 H 1.1562 0.5583 0.7167 0.028 Uiso 1 1 calc R . .
C31 C 1.0529(2) 0.43457(15) 0.81687(14) 0.0183(4) Uani 1 1 d . . .
N32 N 1.03718(19) 0.37343(13) 0.90612(12) 0.0188(4) Uani 1 1 d . . .
H33 H 0.918(3) 0.351(2) 0.7935(18) 0.033(7) Uiso 1 1 d . . .
N33 N 0.9720(2) 0.40639(13) 0.76301(12) 0.0205(4) Uani 1 1 d . . .
C34 C 0.9641(2) 0.45555(16) 0.67075(14) 0.0208(4) Uani 1 1 d . . .
O34 O 1.03197(19) 0.53170(12) 0.62273(11) 0.0306(4) Uani 1 1 d . . .
C35 C 0.8636(2) 0.40795(16) 0.63302(15) 0.0239(5) Uani 1 1 d . . .
H35A H 0.8468 0.3364 0.6743 0.029 Uiso 1 1 calc R . .
H35B H 0.9169 0.4033 0.5704 0.029 Uiso 1 1 calc R . .
C36 C 0.7084(2) 0.46841(18) 0.62488(15) 0.0279(5) Uani 1 1 d . . .
C37 C 0.6209(3) 0.4075(2) 0.5900(2) 0.0520(8) Uani 1 1 d . . .
H37A H 0.5203 0.4427 0.5852 0.078 Uiso 1 1 calc R . .
H37B H 0.6102 0.3375 0.6340 0.078 Uiso 1 1 calc R . .
H37C H 0.6755 0.4029 0.5284 0.078 Uiso 1 1 calc R . .
C38 C 0.6239(3) 0.4760(3) 0.72102(18) 0.0475(7) Uani 1 1 d . . .
H38A H 0.5237 0.5120 0.7163 0.071 Uiso 1 1 calc R . .
H38B H 0.6814 0.5149 0.7435 0.071 Uiso 1 1 calc R . .
H38C H 0.6123 0.4061 0.7650 0.071 Uiso 1 1 calc R . .
C39 C 0.7258(3) 0.57669(18) 0.55547(17) 0.0326(5) Uani 1 1 d . . .
H39A H 0.7794 0.5710 0.4940 0.049 Uiso 1 1 calc R . .
H39B H 0.7836 0.6162 0.5770 0.049 Uiso 1 1 calc R . .
H39C H 0.6255 0.6124 0.5508 0.049 Uiso 1 1 calc R . .
C41 C 0.4301(2) -0.36680(16) 1.02254(16) 0.0254(5) Uani 1 1 d . . .
H41A H 0.4555 -0.4073 1.0828 0.038 Uiso 1 1 calc R . .
H41B H 0.4714 -0.4044 0.9765 0.038 Uiso 1 1 calc R . .
H41C H 0.3199 -0.3561 1.0296 0.038 Uiso 1 1 calc R . .
C51 C 0.4109(3) -0.22697(18) 0.83715(16) 0.0277(5) Uani 1 1 d . . .
H51A H 0.4030 -0.1682 0.7813 0.042 Uiso 1 1 calc R . .
H51B H 0.3094 -0.2475 0.8712 0.042 Uiso 1 1 calc R . .
H51C H 0.4701 -0.2855 0.8186 0.042 Uiso 1 1 calc R . .
C1S C 0.6440(3) 0.1372(2) 0.4493(2) 0.0385(6) Uani 1 1 d . . .
H1S1 H 0.6277 0.1146 0.5183 0.046 Uiso 1 1 calc R . .
H1S2 H 0.7318 0.0945 0.4253 0.046 Uiso 1 1 calc R . .
Cl1 Cl 0.68397(9) 0.26764(6) 0.40638(7) 0.0677(3) Uani 1 1 d . . .
Cl2 Cl 0.48247(8) 0.11712(7) 0.41569(5) 0.0591(3) 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
N1 0.0179(8) 0.0149(8) 0.0180(8) -0.0034(7) -0.0016(7) -0.0028(6)
C2 0.0147(9) 0.0173(9) 0.0201(10) -0.0068(8) -0.0015(8) -0.0007(7)
C3 0.0193(10) 0.0176(10) 0.0203(10) -0.0046(8) -0.0011(8) -0.0018(8)
C4 0.0176(10) 0.0183(10) 0.0267(11) -0.0089(8) 0.0011(8) -0.0017(8)
C5 0.0177(10) 0.0218(10) 0.0248(11) -0.0116(8) -0.0018(8) -0.0010(8)
C6 0.0183(10) 0.0201(10) 0.0208(10) -0.0069(8) -0.0047(8) -0.0001(8)
C7 0.0155(9) 0.0160(9) 0.0204(10) -0.0049(8) -0.0013(8) -0.0003(7)
N8 0.0168(8) 0.0177(8) 0.0196(9) -0.0050(7) -0.0027(7) -0.0019(7)
C9 0.0146(9) 0.0156(9) 0.0175(10) -0.0044(8) -0.0009(7) -0.0023(7)
C10 0.0165(9) 0.0153(9) 0.0190(10) -0.0038(8) -0.0024(8) -0.0029(7)
O10 0.0280(8) 0.0205(7) 0.0203(7) -0.0007(6) -0.0065(6) -0.0080(6)
N11 0.0199(9) 0.0158(8) 0.0193(9) -0.0030(7) -0.0024(7) -0.0048(7)
C12 0.0162(9) 0.0173(9) 0.0190(10) -0.0049(8) -0.0022(8) -0.0008(7)
O12 0.0264(8) 0.0225(7) 0.0249(8) -0.0057(6) -0.0085(6) -0.0059(6)
N13 0.0194(8) 0.0181(8) 0.0185(8) -0.0054(7) -0.0035(7) -0.0024(7)
C14 0.0143(9) 0.0159(9) 0.0186(10) -0.0041(8) 0.0000(8) -0.0014(7)
C15 0.0215(10) 0.0171(9) 0.0184(10) -0.0012(8) -0.0046(8) -0.0024(8)
C16 0.0186(10) 0.0224(10) 0.0196(10) -0.0044(8) -0.0028(8) -0.0022(8)
C17 0.0248(11) 0.0251(11) 0.0201(10) -0.0011(8) -0.0041(9) -0.0074(9)
C18 0.0244(11) 0.0235(11) 0.0216(11) -0.0027(8) -0.0064(9) -0.0027(8)
C19 0.0232(11) 0.0261(11) 0.0252(11) -0.0046(9) -0.0059(9) -0.0040(9)
C20 0.0238(11) 0.0279(11) 0.0250(11) -0.0078(9) -0.0044(9) -0.0042(9)
O20 0.0214(8) 0.0303(8) 0.0280(8) -0.0093(7) -0.0048(6) -0.0055(6)
C21 0.0242(11) 0.0330(12) 0.0168(10) -0.0022(9) -0.0068(8) -0.0055(9)
O21 0.0240(8) 0.0339(9) 0.0401(10) -0.0074(7) -0.0112(7) -0.0013(7)
C22 0.0249(11) 0.0329(12) 0.0221(11) -0.0090(9) -0.0067(9) -0.0047(9)
C23 0.0255(11) 0.0275(11) 0.0227(11) -0.0079(9) -0.0075(9) -0.0044(9)
C24 0.0230(11) 0.0230(11) 0.0251(11) -0.0084(9) -0.0060(9) -0.0017(8)
C25 0.0184(10) 0.0215(10) 0.0258(11) -0.0103(8) -0.0062(8) 0.0016(8)
O25 0.0284(8) 0.0269(8) 0.0288(8) -0.0105(7) -0.0078(7) -0.0069(7)
N26 0.0211(9) 0.0185(9) 0.0217(9) -0.0058(7) -0.0063(7) -0.0039(7)
C27 0.0175(9) 0.0162(9) 0.0209(10) -0.0069(8) -0.0040(8) 0.0009(7)
C28 0.0204(10) 0.0216(10) 0.0268(11) -0.0096(9) -0.0058(9) -0.0044(8)
C29 0.0215(10) 0.0193(10) 0.0307(12) -0.0075(9) -0.0041(9) -0.0052(8)
C30 0.0242(11) 0.0198(10) 0.0232(11) -0.0034(8) -0.0035(9) -0.0050(8)
C31 0.0184(10) 0.0170(9) 0.0203(10) -0.0066(8) -0.0042(8) -0.0008(8)
N32 0.0181(8) 0.0172(8) 0.0204(9) -0.0052(7) -0.0035(7) -0.0011(6)
N33 0.0225(9) 0.0176(8) 0.0204(9) -0.0020(7) -0.0046(7) -0.0066(7)
C34 0.0214(10) 0.0195(10) 0.0203(10) -0.0046(8) -0.0037(8) -0.0018(8)
O34 0.0371(9) 0.0299(8) 0.0224(8) 0.0019(7) -0.0066(7) -0.0163(7)
C35 0.0307(12) 0.0197(10) 0.0207(11) -0.0014(8) -0.0074(9) -0.0067(9)
C36 0.0240(11) 0.0320(12) 0.0227(11) 0.0016(9) -0.0059(9) -0.0071(9)
C37 0.0490(17) 0.0508(17) 0.0557(18) 0.0083(14) -0.0317(15) -0.0234(14)
C38 0.0251(13) 0.074(2) 0.0285(13) -0.0012(13) -0.0004(11) 0.0013(13)
C39 0.0308(12) 0.0313(12) 0.0288(12) -0.0011(10) -0.0071(10) 0.0025(10)
C41 0.0247(11) 0.0207(10) 0.0308(12) -0.0086(9) -0.0018(9) -0.0062(9)
C51 0.0283(12) 0.0275(11) 0.0316(12) -0.0127(10) -0.0058(10) -0.0073(9)
C1S 0.0276(12) 0.0346(14) 0.0498(16) -0.0044(12) -0.0127(11) -0.0022(10)
Cl1 0.0487(4) 0.0311(4) 0.1049(7) -0.0124(4) 0.0076(4) -0.0024(3)
Cl2 0.0319(4) 0.0941(6) 0.0409(4) 0.0046(4) -0.0135(3) -0.0188(4)

_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
N1 C14 1.366(2) . ?
N1 C2 1.384(3) . ?
N1 C15 1.482(2) . ?
C2 C3 1.404(3) . ?
C2 C7 1.417(3) . ?
C3 C4 1.374(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.423(3) . ?
C4 C41 1.501(3) . ?
C5 C6 1.370(3) . ?
C5 C51 1.501(3) . ?
C6 C7 1.409(3) . ?
C6 H6 0.9500 . ?
C7 N8 1.364(3) . ?
N8 C9 1.300(3) . ?
C9 C14 1.440(3) . ?
C9 C10 1.487(3) . ?
C10 O10 1.224(2) . ?
C10 N11 1.357(3) . ?
N11 C12 1.399(3) . ?
N11 H11 0.84(3) . ?
C12 O12 1.227(2) . ?
C12 N13 1.360(3) . ?
N13 C14 1.320(3) . ?
C15 C16 1.521(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.526(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.531(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.522(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.508(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O20 1.448(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
O20 C21 1.340(3) . ?
C21 O21 1.207(3) . ?
C21 C22 1.506(3) . ?
C22 C23 1.531(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.513(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.514(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 O25 1.213(3) . ?
C25 N26 1.376(3) . ?
N26 C27 1.398(3) . ?
N26 H26 0.90(3) . ?
C27 N32 1.344(3) . ?
C27 C28 1.393(3) . ?
C28 C29 1.379(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.375(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.393(3) . ?
C30 H30 0.9500 . ?
C31 N32 1.348(3) . ?
C31 N33 1.401(3) . ?
N33 C34 1.380(3) . ?
N33 H33 0.89(3) . ?
C34 O34 1.218(2) . ?
C34 C35 1.506(3) . ?
C35 C36 1.544(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.517(4) . ?
C36 C39 1.525(3) . ?
C36 C38 1.529(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C1S Cl1 1.747(3) . ?
C1S Cl2 1.757(3) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?

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
C14 N1 C2 120.79(17) . . ?
C14 N1 C15 117.39(16) . . ?
C2 N1 C15 121.77(16) . . ?
N1 C2 C3 123.30(18) . . ?
N1 C2 C7 117.94(17) . . ?
C3 C2 C7 118.75(18) . . ?
C4 C3 C2 121.12(19) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.34(18) . . ?
C3 C4 C41 120.35(19) . . ?
C5 C4 C41 119.31(19) . . ?
C6 C5 C4 119.01(19) . . ?
C6 C5 C51 120.73(19) . . ?
C4 C5 C51 120.26(18) . . ?
C5 C6 C7 121.50(19) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
N8 C7 C6 118.25(18) . . ?
N8 C7 C2 122.51(18) . . ?
C6 C7 C2 119.24(18) . . ?
C9 N8 C7 117.19(17) . . ?
N8 C9 C14 124.95(17) . . ?
N8 C9 C10 118.62(17) . . ?
C14 C9 C10 116.41(17) . . ?
O10 C10 N11 122.06(17) . . ?
O10 C10 C9 124.07(18) . . ?
N11 C10 C9 113.87(17) . . ?
C10 N11 C12 126.01(17) . . ?
C10 N11 H11 117.7(19) . . ?
C12 N11 H11 116.3(19) . . ?
O12 C12 N13 122.02(18) . . ?
O12 C12 N11 117.83(18) . . ?
N13 C12 N11 120.14(17) . . ?
C14 N13 C12 117.72(17) . . ?
N13 C14 N1 117.82(17) . . ?
N13 C14 C9 125.63(17) . . ?
N1 C14 C9 116.53(18) . . ?
N1 C15 C16 113.50(16) . . ?
N1 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
N1 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 110.35(17) . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C16 C17 C18 114.66(17) . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
C18 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 114.96(18) . . ?
C19 C18 H18A 108.5 . . ?
C17 C18 H18A 108.5 . . ?
C19 C18 H18B 108.5 . . ?
C17 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C20 C19 C18 111.12(18) . . ?
C20 C19 H19A 109.4 . . ?
C18 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
O20 C20 C19 107.17(17) . . ?
O20 C20 H20A 110.3 . . ?
C19 C20 H20A 110.3 . . ?
O20 C20 H20B 110.3 . . ?
C19 C20 H20B 110.3 . . ?
H20A C20 H20B 108.5 . . ?
C21 O20 C20 116.51(17) . . ?
O21 C21 O20 123.1(2) . . ?
O21 C21 C22 125.0(2) . . ?
O20 C21 C22 111.89(18) . . ?
C21 C22 C23 110.55(18) . . ?
C21 C22 H22A 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C24 C23 C22 112.44(17) . . ?
C24 C23 H23A 109.1 . . ?
C22 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C22 C23 H23B 109.1 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 C25 112.99(17) . . ?
C23 C24 H24A 109.0 . . ?
C25 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
C25 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
O25 C25 N26 124.6(2) . . ?
O25 C25 C24 122.87(19) . . ?
N26 C25 C24 112.57(17) . . ?
C25 N26 C27 128.03(18) . . ?
C25 N26 H26 113.9(16) . . ?
C27 N26 H26 117.9(16) . . ?
N32 C27 C28 123.28(18) . . ?
N32 C27 N26 114.06(17) . . ?
C28 C27 N26 122.66(18) . . ?
C29 C28 C27 117.29(19) . . ?
C29 C28 H28 121.4 . . ?
C27 C28 H28 121.4 . . ?
C30 C29 C28 121.12(19) . . ?
C30 C29 H29 119.4 . . ?
C28 C29 H29 119.4 . . ?
C29 C30 C31 117.71(19) . . ?
C29 C30 H30 121.1 . . ?
C31 C30 H30 121.1 . . ?
N32 C31 C30 122.81(19) . . ?
N32 C31 N33 114.55(17) . . ?
C30 C31 N33 122.63(18) . . ?
C27 N32 C31 117.75(17) . . ?
C34 N33 C31 127.40(18) . . ?
C34 N33 H33 117.8(17) . . ?
C31 N33 H33 114.7(17) . . ?
O34 C34 N33 123.33(19) . . ?
O34 C34 C35 121.87(19) . . ?
N33 C34 C35 114.80(18) . . ?
C34 C35 C36 114.24(18) . . ?
C34 C35 H35A 108.7 . . ?
C36 C35 H35A 108.7 . . ?
C34 C35 H35B 108.7 . . ?
C36 C35 H35B 108.7 . . ?
H35A C35 H35B 107.6 . . ?
C37 C36 C39 109.0(2) . . ?
C37 C36 C38 109.8(2) . . ?
C39 C36 C38 110.0(2) . . ?
C37 C36 C35 107.0(2) . . ?
C39 C36 C35 111.44(18) . . ?
C38 C36 C35 109.53(19) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C4 C41 H41A 109.5 . . ?
C4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
Cl1 C1S Cl2 111.45(14) . . ?
Cl1 C1S H1S1 109.3 . . ?
Cl2 C1S H1S1 109.3 . . ?
Cl1 C1S H1S2 109.3 . . ?
Cl2 C1S H1S2 109.3 . . ?
H1S1 C1S H1S2 108.0 . . ?

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
C14 N1 C2 C3 -177.79(18) . . . . ?
C15 N1 C2 C3 4.8(3) . . . . ?
C14 N1 C2 C7 2.4(3) . . . . ?
C15 N1 C2 C7 -175.01(17) . . . . ?
N1 C2 C3 C4 -177.48(18) . . . . ?
C7 C2 C3 C4 2.3(3) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C2 C3 C4 C41 177.53(18) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C41 C4 C5 C6 -178.45(18) . . . . ?
C3 C4 C5 C51 179.76(18) . . . . ?
C41 C4 C5 C51 0.7(3) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C51 C5 C6 C7 -179.72(18) . . . . ?
C5 C6 C7 N8 -178.10(18) . . . . ?
C5 C6 C7 C2 1.4(3) . . . . ?
N1 C2 C7 N8 -3.0(3) . . . . ?
C3 C2 C7 N8 177.24(18) . . . . ?
N1 C2 C7 C6 177.58(17) . . . . ?
C3 C2 C7 C6 -2.2(3) . . . . ?
C6 C7 N8 C9 -179.61(17) . . . . ?
C2 C7 N8 C9 0.9(3) . . . . ?
C7 N8 C9 C14 1.7(3) . . . . ?
C7 N8 C9 C10 -179.62(17) . . . . ?
N8 C9 C10 O10 0.4(3) . . . . ?
C14 C9 C10 O10 179.15(19) . . . . ?
N8 C9 C10 N11 -179.77(17) . . . . ?
C14 C9 C10 N11 -1.0(2) . . . . ?
O10 C10 N11 C12 -175.49(19) . . . . ?
C9 C10 N11 C12 4.6(3) . . . . ?
C10 N11 C12 O12 174.78(18) . . . . ?
C10 N11 C12 N13 -5.1(3) . . . . ?
O12 C12 N13 C14 -178.59(18) . . . . ?
N11 C12 N13 C14 1.3(3) . . . . ?
C12 N13 C14 N1 -179.30(17) . . . . ?
C12 N13 C14 C9 2.3(3) . . . . ?
C2 N1 C14 N13 -178.61(17) . . . . ?
C15 N1 C14 N13 -1.1(3) . . . . ?
C2 N1 C14 C9 -0.1(3) . . . . ?
C15 N1 C14 C9 177.45(16) . . . . ?
N8 C9 C14 N13 176.24(18) . . . . ?
C10 C9 C14 N13 -2.5(3) . . . . ?
N8 C9 C14 N1 -2.2(3) . . . . ?
C10 C9 C14 N1 179.14(16) . . . . ?
C14 N1 C15 C16 81.5(2) . . . . ?
C2 N1 C15 C16 -101.0(2) . . . . ?
N1 C15 C16 C17 -172.34(16) . . . . ?
C15 C16 C17 C18 64.4(2) . . . . ?
C16 C17 C18 C19 63.5(3) . . . . ?
C17 C18 C19 C20 -177.97(18) . . . . ?
C18 C19 C20 O20 -169.89(17) . . . . ?
C19 C20 O20 C21 -175.41(17) . . . . ?
C20 O20 C21 O21 -2.7(3) . . . . ?
C20 O20 C21 C22 175.15(17) . . . . ?
O21 C21 C22 C23 71.1(3) . . . . ?
O20 C21 C22 C23 -106.6(2) . . . . ?
C21 C22 C23 C24 56.9(2) . . . . ?
C22 C23 C24 C25 174.97(18) . . . . ?
C23 C24 C25 O25 -5.7(3) . . . . ?
C23 C24 C25 N26 174.58(17) . . . . ?
O25 C25 N26 C27 -2.0(3) . . . . ?
C24 C25 N26 C27 177.67(18) . . . . ?
C25 N26 C27 N32 -177.19(18) . . . . ?
C25 N26 C27 C28 3.8(3) . . . . ?
N32 C27 C28 C29 -1.4(3) . . . . ?
N26 C27 C28 C29 177.56(18) . . . . ?
C27 C28 C29 C30 0.9(3) . . . . ?
C28 C29 C30 C31 0.7(3) . . . . ?
C29 C30 C31 N32 -2.1(3) . . . . ?
C29 C30 C31 N33 179.18(18) . . . . ?
C28 C27 N32 C31 0.1(3) . . . . ?
N26 C27 N32 C31 -178.93(17) . . . . ?
C30 C31 N32 C27 1.7(3) . . . . ?
N33 C31 N32 C27 -179.51(16) . . . . ?
N32 C31 N33 C34 178.54(19) . . . . ?
C30 C31 N33 C34 -2.7(3) . . . . ?
C31 N33 C34 O34 1.5(3) . . . . ?
C31 N33 C34 C35 -178.37(18) . . . . ?
O34 C34 C35 C36 -76.7(3) . . . . ?
N33 C34 C35 C36 103.2(2) . . . . ?
C34 C35 C36 C37 -177.64(19) . . . . ?
C34 C35 C36 C39 63.3(3) . . . . ?
C34 C35 C36 C38 -58.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N26 H26 O12 0.90(3) 1.96(3) 2.843(2) 167(2) .
N33 H33 O10 0.89(3) 2.09(3) 2.967(2) 167(2) .
N11 H11 N32 0.84(3) 2.21(3) 3.039(2) 169(3) .

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.120
_refine_diff_density_min         -1.030
_refine_diff_density_rms         0.101