# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# 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_mac87_3a
#TrackingRef '14897_web_deposit_cif_file_0_BillClegg_1351029791.combined.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N2'
_chemical_formula_sum            'C13 H10 N2'
_chemical_formula_weight         194.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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/c'

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

_cell_length_a                   28.7348(14)
_cell_length_b                   5.8963(2)
_cell_length_c                   23.3995(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.806(3)
_cell_angle_gamma                90.00
_cell_volume                     3964.2(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4237
_cell_measurement_theta_min      1.89
_cell_measurement_theta_max      62.18

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'sealed tube with Enhance Ultra optics'
_diffrn_radiation_monochromator  none
_diffrn_measurement_device_type  
'Oxford Diffraction Gemini A Ultra diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.3968
_diffrn_reflns_number            11230
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         62.27
_reflns_number_total             6140
_reflns_number_gt                4212
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan 5 2010,16:28:46)
;
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'

_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^)+(0.1460P)^2^+0.6250P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6140
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0784
_refine_ls_wR_factor_ref         0.2275
_refine_ls_wR_factor_gt          0.2092
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
N1 N 0.23645(10) 0.6139(6) 0.59419(12) 0.0443(8) Uani 1 1 d . . .
C2 C 0.26328(13) 0.7828(7) 0.62274(16) 0.0470(10) Uani 1 1 d . . .
H2 H 0.2688 0.9269 0.6060 0.056 Uiso 1 1 calc R . .
C3 C 0.28055(13) 0.7281(7) 0.67485(16) 0.0472(10) Uani 1 1 d . . .
H3 H 0.2994 0.8349 0.6948 0.057 Uiso 1 1 calc R . .
C4 C 0.27143(14) 0.5202(8) 0.70001(17) 0.0534(11) Uani 1 1 d . . .
H4 H 0.2834 0.4900 0.7373 0.064 Uiso 1 1 calc R . .
C5 C 0.24634(14) 0.3616(8) 0.67322(16) 0.0531(10) Uani 1 1 d . . .
H5 H 0.2408 0.2198 0.6912 0.064 Uiso 1 1 calc R . .
C6 C 0.22857(13) 0.4036(6) 0.61993(16) 0.0423(9) Uani 1 1 d . . .
N7 N 0.20342(11) 0.2734(6) 0.58246(13) 0.0471(8) Uani 1 1 d . . .
C8 C 0.19522(12) 0.4073(6) 0.53583(14) 0.0343(8) Uani 1 1 d . . .
C9 C 0.21551(13) 0.6162(7) 0.54106(16) 0.0464(9) Uani 1 1 d . . .
H9 H 0.2152 0.7362 0.5140 0.056 Uiso 1 1 calc R . .
C10 C 0.16773(13) 0.3196(7) 0.48528(16) 0.0434(9) Uani 1 1 d . . .
C11 C 0.14645(13) 0.1109(7) 0.48964(15) 0.0481(10) Uani 1 1 d . . .
H11 H 0.1500 0.0247 0.5237 0.058 Uiso 1 1 calc R . .
C12 C 0.11912(14) 0.0237(7) 0.44311(18) 0.0522(10) Uani 1 1 d . . .
H12 H 0.1053 -0.1222 0.4453 0.063 Uiso 1 1 calc R . .
C13 C 0.11326(13) 0.1570(7) 0.39476(15) 0.0461(10) Uani 1 1 d . . .
H13 H 0.0942 0.1073 0.3637 0.055 Uiso 1 1 calc R . .
C14 C 0.13565(13) 0.3619(7) 0.39278(17) 0.0491(10) Uani 1 1 d . . .
H14 H 0.1321 0.4535 0.3596 0.059 Uiso 1 1 calc R . .
C15 C 0.16274(14) 0.4384(8) 0.43681(17) 0.0510(10) Uani 1 1 d . . .
H15 H 0.1785 0.5793 0.4331 0.061 Uiso 1 1 calc R . .
N21 N 0.51934(10) 0.4290(5) 0.61767(12) 0.0383(7) Uani 1 1 d . . .
C22 C 0.55650(13) 0.3623(7) 0.58438(17) 0.0476(10) Uani 1 1 d . . .
H22 H 0.5713 0.2202 0.5906 0.057 Uiso 1 1 calc R . .
C23 C 0.57130(13) 0.5033(8) 0.54293(16) 0.0489(10) Uani 1 1 d . . .
H23 H 0.5968 0.4606 0.5200 0.059 Uiso 1 1 calc R . .
C24 C 0.54901(14) 0.7140(8) 0.53353(16) 0.0502(10) Uani 1 1 d . . .
H24 H 0.5595 0.8114 0.5041 0.060 Uiso 1 1 calc R . .
C25 C 0.51307(13) 0.7777(7) 0.56590(15) 0.0463(9) Uani 1 1 d . . .
H25 H 0.4980 0.9184 0.5586 0.056 Uiso 1 1 calc R . .
C26 C 0.49775(12) 0.6395(6) 0.60996(14) 0.0361(8) Uani 1 1 d . . .
N27 N 0.46466(10) 0.6714(5) 0.64857(12) 0.0384(7) Uani 1 1 d . . .
C28 C 0.46545(12) 0.4785(6) 0.68132(14) 0.0344(8) Uani 1 1 d . . .
C29 C 0.49833(12) 0.3288(6) 0.66316(15) 0.0406(9) Uani 1 1 d . . .
H29 H 0.5052 0.1840 0.6790 0.049 Uiso 1 1 calc R . .
C30 C 0.43302(12) 0.4538(6) 0.72962(14) 0.0370(8) Uani 1 1 d . . .
C31 C 0.43144(14) 0.2576(7) 0.76192(16) 0.0492(10) Uani 1 1 d . . .
H31 H 0.4512 0.1339 0.7528 0.059 Uiso 1 1 calc R . .
C32 C 0.40131(15) 0.2394(8) 0.80746(17) 0.0556(11) Uani 1 1 d . . .
H32 H 0.4002 0.1023 0.8288 0.067 Uiso 1 1 calc R . .
C33 C 0.37318(14) 0.4163(8) 0.82205(16) 0.0523(11) Uani 1 1 d . . .
H33 H 0.3535 0.4048 0.8542 0.063 Uiso 1 1 calc R . .
C34 C 0.37364(14) 0.6141(8) 0.78929(16) 0.0525(11) Uani 1 1 d . . .
H34 H 0.3534 0.7360 0.7981 0.063 Uiso 1 1 calc R . .
C35 C 0.40378(14) 0.6316(7) 0.74397(16) 0.0473(10) Uani 1 1 d . . .
H35 H 0.4045 0.7677 0.7223 0.057 Uiso 1 1 calc R . .
N41 N 0.32427(9) 1.1515(5) 0.52118(11) 0.0326(7) Uani 1 1 d . . .
C42 C 0.33347(12) 1.3254(6) 0.55951(14) 0.0377(8) Uani 1 1 d . . .
H42 H 0.3179 1.4669 0.5559 0.045 Uiso 1 1 calc R . .
C43 C 0.36467(12) 1.2914(6) 0.60186(15) 0.0382(8) Uani 1 1 d . . .
H43 H 0.3709 1.4089 0.6287 0.046 Uiso 1 1 calc R . .
C44 C 0.38840(12) 1.0818(6) 0.60690(14) 0.0380(8) Uani 1 1 d . . .
H44 H 0.4104 1.0596 0.6371 0.046 Uiso 1 1 calc R . .
C45 C 0.37987(12) 0.9124(6) 0.56888(14) 0.0390(8) Uani 1 1 d . . .
H45 H 0.3962 0.7729 0.5723 0.047 Uiso 1 1 calc R . .
C46 C 0.34718(12) 0.9422(6) 0.52467(14) 0.0336(8) Uani 1 1 d . . .
N47 N 0.33194(10) 0.8035(5) 0.48336(11) 0.0365(7) Uani 1 1 d . . .
C48 C 0.29887(11) 0.9233(6) 0.45287(13) 0.0337(8) Uani 1 1 d . . .
C49 C 0.29329(12) 1.1365(6) 0.47545(14) 0.0363(8) Uani 1 1 d . . .
H49 H 0.2724 1.2506 0.4623 0.044 Uiso 1 1 calc R . .
C50 C 0.27419(12) 0.8221(6) 0.40350(13) 0.0358(8) Uani 1 1 d . . .
C51 C 0.23594(12) 0.9286(7) 0.37854(14) 0.0413(9) Uani 1 1 d . . .
H51 H 0.2253 1.0690 0.3934 0.050 Uiso 1 1 calc R . .
C52 C 0.21320(13) 0.8310(7) 0.33196(15) 0.0474(10) Uani 1 1 d . . .
H52 H 0.1873 0.9065 0.3150 0.057 Uiso 1 1 calc R . .
C53 C 0.22770(13) 0.6254(7) 0.30982(14) 0.0466(10) Uani 1 1 d . . .
H53 H 0.2118 0.5593 0.2780 0.056 Uiso 1 1 calc R . .
C54 C 0.26546(14) 0.5183(7) 0.33462(15) 0.0462(9) Uani 1 1 d . . .
H54 H 0.2757 0.3769 0.3200 0.055 Uiso 1 1 calc R . .
C55 C 0.28885(13) 0.6167(6) 0.38126(14) 0.0410(9) Uani 1 1 d . . .
H55 H 0.3150 0.5420 0.3978 0.049 Uiso 1 1 calc R . .
N61 N -0.00866(11) 1.0453(6) 0.86370(13) 0.0476(8) Uani 1 1 d . . .
C62 C -0.04203(15) 1.1474(8) 0.89421(18) 0.0562(11) Uani 1 1 d . . .
H62 H -0.0542 1.2899 0.8824 0.067 Uiso 1 1 calc R . .
C63 C -0.05802(15) 1.0451(11) 0.9419(2) 0.0715(15) Uani 1 1 d . . .
H63 H -0.0810 1.1166 0.9644 0.086 Uiso 1 1 calc R . .
C64 C -0.03960(15) 0.8244(10) 0.95826(17) 0.0647(14) Uani 1 1 d . . .
H64 H -0.0506 0.7496 0.9914 0.078 Uiso 1 1 calc R . .
C65 C -0.00665(15) 0.7273(8) 0.92583(17) 0.0557(11) Uani 1 1 d . . .
H65 H 0.0057 0.5834 0.9362 0.067 Uiso 1 1 calc R . .
C66 C 0.00917(13) 0.8371(7) 0.87745(16) 0.0451(9) Uani 1 1 d . . .
N67 N 0.04101(11) 0.7719(5) 0.83880(14) 0.0486(8) Uani 1 1 d . . .
C68 C 0.04291(12) 0.9461(6) 0.80126(15) 0.0412(9) Uani 1 1 d . . .
C69 C 0.01338(14) 1.1166(7) 0.81452(16) 0.0481(10) Uani 1 1 d . . .
H69 H 0.0088 1.2551 0.7945 0.058 Uiso 1 1 calc R . .
C70 C 0.07652(12) 0.9415(8) 0.75335(14) 0.0447(10) Uani 1 1 d . . .
C71 C 0.08132(14) 1.1242(7) 0.71570(17) 0.0521(10) Uani 1 1 d . . .
H71 H 0.0623 1.2550 0.7195 0.063 Uiso 1 1 calc R . .
C72 C 0.11440(15) 1.1127(8) 0.67242(17) 0.0554(11) Uani 1 1 d . . .
H72 H 0.1181 1.2383 0.6475 0.066 Uiso 1 1 calc R . .
C73 C 0.14078(14) 0.9298(8) 0.66546(17) 0.0552(11) Uani 1 1 d . . .
H73 H 0.1628 0.9257 0.6356 0.066 Uiso 1 1 calc R . .
C74 C 0.13631(14) 0.7489(8) 0.70088(18) 0.0540(11) Uani 1 1 d . . .
H74 H 0.1554 0.6193 0.6956 0.065 Uiso 1 1 calc R . .
C75 C 0.10489(14) 0.7506(7) 0.74372(16) 0.0466(10) Uani 1 1 d . . .
H75 H 0.1020 0.6211 0.7676 0.056 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0431(18) 0.053(2) 0.0367(16) -0.0036(15) 0.0000(13) 0.0142(16)
C2 0.050(2) 0.036(2) 0.056(2) 0.0002(19) 0.0162(18) 0.0042(18)
C3 0.045(2) 0.051(3) 0.045(2) -0.016(2) -0.0026(16) 0.0008(19)
C4 0.059(3) 0.057(3) 0.044(2) -0.002(2) 0.0055(18) 0.010(2)
C5 0.060(3) 0.051(3) 0.048(2) -0.001(2) 0.0061(19) 0.002(2)
C6 0.044(2) 0.028(2) 0.055(2) -0.0049(18) 0.0075(17) 0.0020(17)
N7 0.059(2) 0.0358(18) 0.0471(17) 0.0076(15) 0.0065(15) 0.0015(16)
C8 0.0393(19) 0.0263(18) 0.0376(17) 0.0049(15) 0.0034(14) 0.0040(15)
C9 0.055(2) 0.036(2) 0.048(2) 0.0049(18) 0.0053(17) 0.0068(19)
C10 0.040(2) 0.037(2) 0.054(2) -0.0063(18) 0.0109(16) 0.0022(18)
C11 0.053(2) 0.053(3) 0.039(2) 0.0132(19) 0.0057(17) 0.020(2)
C12 0.050(2) 0.035(2) 0.073(3) 0.004(2) 0.012(2) 0.0022(19)
C13 0.044(2) 0.053(3) 0.041(2) -0.0110(19) -0.0054(16) 0.0112(19)
C14 0.048(2) 0.049(3) 0.051(2) 0.009(2) -0.0050(17) 0.003(2)
C15 0.048(2) 0.045(2) 0.060(2) 0.000(2) 0.0028(19) 0.0020(19)
N21 0.0420(17) 0.0318(16) 0.0411(16) -0.0012(14) -0.0060(13) -0.0035(14)
C22 0.043(2) 0.037(2) 0.062(2) -0.016(2) -0.0104(18) 0.0127(18)
C23 0.045(2) 0.055(3) 0.047(2) -0.014(2) 0.0054(17) 0.001(2)
C24 0.052(2) 0.052(3) 0.047(2) 0.0052(19) 0.0012(18) 0.002(2)
C25 0.050(2) 0.040(2) 0.049(2) 0.0039(18) -0.0041(17) 0.0037(19)
C26 0.0355(19) 0.0280(19) 0.0449(19) -0.0022(16) -0.0036(15) 0.0038(15)
N27 0.0403(17) 0.0276(16) 0.0471(16) 0.0050(14) -0.0041(13) 0.0020(13)
C28 0.0377(18) 0.0247(18) 0.0406(18) 0.0002(15) -0.0121(14) 0.0000(15)
C29 0.044(2) 0.0251(18) 0.053(2) 0.0006(17) -0.0102(16) 0.0045(17)
C30 0.0338(18) 0.037(2) 0.0405(18) -0.0022(16) -0.0097(14) -0.0044(16)
C31 0.049(2) 0.042(2) 0.056(2) 0.006(2) -0.0076(18) 0.0051(19)
C32 0.060(3) 0.054(3) 0.053(2) 0.018(2) -0.0098(19) -0.005(2)
C33 0.053(2) 0.068(3) 0.0359(19) 0.000(2) -0.0022(16) -0.014(2)
C34 0.047(2) 0.056(3) 0.054(2) -0.016(2) -0.0031(18) 0.003(2)
C35 0.057(2) 0.039(2) 0.046(2) 0.0083(18) -0.0039(18) -0.010(2)
N41 0.0345(15) 0.0293(16) 0.0342(14) 0.0025(13) 0.0030(11) 0.0030(12)
C42 0.039(2) 0.0290(19) 0.0453(19) 0.0008(16) 0.0076(16) 0.0060(16)
C43 0.040(2) 0.032(2) 0.0422(19) -0.0017(16) 0.0017(15) -0.0004(16)
C44 0.0381(19) 0.038(2) 0.0379(18) 0.0045(16) -0.0041(14) -0.0010(17)
C45 0.040(2) 0.031(2) 0.0453(19) 0.0020(17) -0.0026(15) 0.0036(16)
C46 0.0390(19) 0.0242(18) 0.0378(17) 0.0021(15) 0.0051(14) 0.0037(15)
N47 0.0452(17) 0.0242(15) 0.0399(15) 0.0035(13) -0.0015(13) 0.0048(13)
C48 0.0345(18) 0.0314(19) 0.0354(17) 0.0066(15) 0.0040(14) 0.0036(15)
C49 0.0379(19) 0.0316(19) 0.0394(18) 0.0088(16) 0.0023(15) 0.0069(16)
C50 0.042(2) 0.0319(19) 0.0336(17) 0.0054(15) 0.0040(14) -0.0010(16)
C51 0.045(2) 0.044(2) 0.0356(18) 0.0018(17) 0.0021(15) 0.0049(18)
C52 0.046(2) 0.056(3) 0.040(2) 0.0091(19) -0.0041(16) 0.001(2)
C53 0.051(2) 0.056(3) 0.0326(18) 0.0054(18) -0.0010(16) -0.009(2)
C54 0.057(2) 0.038(2) 0.043(2) -0.0026(17) 0.0086(17) 0.0006(19)
C55 0.046(2) 0.035(2) 0.0420(19) 0.0062(17) 0.0006(15) 0.0014(17)
N61 0.0437(18) 0.051(2) 0.0483(18) -0.0039(16) -0.0072(14) -0.0117(16)
C62 0.061(3) 0.050(3) 0.057(2) -0.013(2) -0.012(2) 0.000(2)
C63 0.045(2) 0.106(4) 0.064(3) -0.042(3) -0.002(2) 0.002(3)
C64 0.056(3) 0.096(4) 0.042(2) 0.009(2) -0.0039(19) -0.034(3)
C65 0.058(3) 0.048(3) 0.061(3) 0.002(2) -0.014(2) -0.009(2)
C66 0.041(2) 0.047(2) 0.047(2) -0.0048(19) -0.0063(16) -0.0099(19)
N67 0.0495(19) 0.0360(18) 0.060(2) 0.0089(16) -0.0116(15) -0.0052(15)
C68 0.043(2) 0.0273(19) 0.053(2) 0.0036(17) -0.0215(17) -0.0027(17)
C69 0.054(2) 0.037(2) 0.053(2) 0.0060(18) -0.0125(18) -0.0091(19)
C70 0.035(2) 0.063(3) 0.0356(18) -0.0031(19) -0.0070(15) -0.0186(19)
C71 0.053(2) 0.036(2) 0.067(3) -0.006(2) -0.019(2) 0.0052(19)
C72 0.061(3) 0.055(3) 0.050(2) 0.017(2) -0.0069(19) -0.022(2)
C73 0.047(2) 0.067(3) 0.051(2) -0.001(2) -0.0032(18) -0.004(2)
C74 0.048(2) 0.051(3) 0.063(2) -0.006(2) -0.0063(19) 0.009(2)
C75 0.053(2) 0.036(2) 0.049(2) 0.0156(18) -0.0143(18) -0.0079(19)

_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 C2 1.421(5) . ?
N1 C6 1.398(5) . ?
N1 C9 1.374(5) . ?
C2 H2 0.950 . ?
C2 C3 1.349(5) . ?
C3 H3 0.950 . ?
C3 C4 1.387(6) . ?
C4 H4 0.950 . ?
C4 C5 1.332(6) . ?
C5 H5 0.950 . ?
C5 C6 1.363(5) . ?
C6 N7 1.365(5) . ?
N7 C8 1.365(4) . ?
C8 C9 1.367(5) . ?
C8 C10 1.505(5) . ?
C9 H9 0.950 . ?
C10 C11 1.378(6) . ?
C10 C15 1.339(5) . ?
C11 H11 0.950 . ?
C11 C12 1.429(6) . ?
C12 H12 0.950 . ?
C12 C13 1.386(5) . ?
C13 H13 0.950 . ?
C13 C14 1.370(6) . ?
C14 H14 0.950 . ?
C14 C15 1.360(6) . ?
C15 H15 0.950 . ?
N21 C22 1.388(5) . ?
N21 C26 1.399(4) . ?
N21 C29 1.365(5) . ?
C22 H22 0.950 . ?
C22 C23 1.351(6) . ?
C23 H23 0.950 . ?
C23 C24 1.413(6) . ?
C24 H24 0.950 . ?
C24 C25 1.343(5) . ?
C25 H25 0.950 . ?
C25 C26 1.391(5) . ?
C26 N27 1.334(4) . ?
N27 C28 1.371(4) . ?
C28 C29 1.365(5) . ?
C28 C30 1.482(5) . ?
C29 H29 0.950 . ?
C30 C31 1.383(5) . ?
C30 C35 1.388(5) . ?
C31 H31 0.950 . ?
C31 C32 1.387(6) . ?
C32 H32 0.950 . ?
C32 C33 1.366(6) . ?
C33 H33 0.950 . ?
C33 C34 1.396(6) . ?
C34 H34 0.950 . ?
C34 C35 1.382(5) . ?
C35 H35 0.950 . ?
N41 C42 1.385(4) . ?
N41 C46 1.401(4) . ?
N41 C49 1.385(4) . ?
C42 H42 0.950 . ?
C42 C43 1.342(5) . ?
C43 H43 0.950 . ?
C43 C44 1.416(5) . ?
C44 H44 0.950 . ?
C44 C45 1.358(5) . ?
C45 H45 0.950 . ?
C45 C46 1.399(5) . ?
C46 N47 1.335(4) . ?
N47 C48 1.375(4) . ?
C48 C49 1.374(5) . ?
C48 C50 1.473(5) . ?
C49 H49 0.950 . ?
C50 C51 1.388(5) . ?
C50 C55 1.386(5) . ?
C51 H51 0.950 . ?
C51 C52 1.388(5) . ?
C52 H52 0.950 . ?
C52 C53 1.385(6) . ?
C53 H53 0.950 . ?
C53 C54 1.376(5) . ?
C54 H54 0.950 . ?
C54 C55 1.399(5) . ?
C55 H55 0.950 . ?
N61 C62 1.346(5) . ?
N61 C66 1.367(5) . ?
N61 C69 1.387(5) . ?
C62 H62 0.950 . ?
C62 C63 1.354(7) . ?
C63 H63 0.950 . ?
C63 C64 1.454(8) . ?
C64 H64 0.950 . ?
C64 C65 1.349(6) . ?
C65 H65 0.950 . ?
C65 C66 1.386(6) . ?
C66 N67 1.351(5) . ?
N67 C68 1.353(5) . ?
C68 C69 1.354(5) . ?
C68 C70 1.490(5) . ?
C69 H69 0.950 . ?
C70 C71 1.400(6) . ?
C70 C75 1.410(6) . ?
C71 H71 0.950 . ?
C71 C72 1.400(6) . ?
C72 H72 0.950 . ?
C72 C73 1.329(6) . ?
C73 H73 0.950 . ?
C73 C74 1.358(6) . ?
C74 H74 0.950 . ?
C74 C75 1.359(6) . ?
C75 H75 0.950 . ?

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 N1 C6 120.6(3) . . ?
C2 N1 C9 130.3(3) . . ?
C6 N1 C9 109.1(3) . . ?
N1 C2 H2 121.7 . . ?
N1 C2 C3 116.6(4) . . ?
H2 C2 C3 121.7 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.7(4) . . ?
H3 C3 C4 119.1 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.7(4) . . ?
H4 C4 C5 119.2 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(4) . . ?
H5 C5 C6 120.1 . . ?
N1 C6 C5 119.6(4) . . ?
N1 C6 N7 108.0(3) . . ?
C5 C6 N7 132.4(4) . . ?
C6 N7 C8 105.8(3) . . ?
N7 C8 C9 112.4(3) . . ?
N7 C8 C10 120.8(3) . . ?
C9 C8 C10 126.8(3) . . ?
N1 C9 C8 104.7(3) . . ?
N1 C9 H9 127.7 . . ?
C8 C9 H9 127.7 . . ?
C8 C10 C11 118.5(3) . . ?
C8 C10 C15 122.3(4) . . ?
C11 C10 C15 119.2(4) . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.3(4) . . ?
H11 C11 C12 119.9 . . ?
C11 C12 H12 120.7 . . ?
C11 C12 C13 118.5(4) . . ?
H12 C12 C13 120.7 . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C14 118.4(4) . . ?
H13 C13 C14 120.8 . . ?
C13 C14 H14 119.0 . . ?
C13 C14 C15 122.1(4) . . ?
H14 C14 C15 119.0 . . ?
C10 C15 C14 121.4(4) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C22 N21 C26 121.5(3) . . ?
C22 N21 C29 131.9(3) . . ?
C26 N21 C29 106.5(3) . . ?
N21 C22 H22 120.6 . . ?
N21 C22 C23 118.8(4) . . ?
H22 C22 C23 120.6 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.4(3) . . ?
H23 C23 C24 119.8 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.6(4) . . ?
H24 C24 C25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C24 C25 C26 120.6(4) . . ?
H25 C25 C26 119.7 . . ?
N21 C26 C25 118.1(3) . . ?
N21 C26 N27 110.9(3) . . ?
C25 C26 N27 131.0(3) . . ?
C26 N27 C28 104.8(3) . . ?
N27 C28 C29 111.6(3) . . ?
N27 C28 C30 120.1(3) . . ?
C29 C28 C30 128.3(3) . . ?
N21 C29 C28 106.2(3) . . ?
N21 C29 H29 126.9 . . ?
C28 C29 H29 126.9 . . ?
C28 C30 C31 121.6(3) . . ?
C28 C30 C35 120.0(3) . . ?
C31 C30 C35 118.4(3) . . ?
C30 C31 H31 119.7 . . ?
C30 C31 C32 120.7(4) . . ?
H31 C31 C32 119.7 . . ?
C31 C32 H32 119.6 . . ?
C31 C32 C33 120.7(4) . . ?
H32 C32 C33 119.6 . . ?
C32 C33 H33 120.3 . . ?
C32 C33 C34 119.4(4) . . ?
H33 C33 C34 120.3 . . ?
C33 C34 H34 120.2 . . ?
C33 C34 C35 119.6(4) . . ?
H34 C34 C35 120.2 . . ?
C30 C35 C34 121.1(4) . . ?
C30 C35 H35 119.4 . . ?
C34 C35 H35 119.4 . . ?
C42 N41 C46 122.0(3) . . ?
C42 N41 C49 131.5(3) . . ?
C46 N41 C49 106.5(3) . . ?
N41 C42 H42 120.4 . . ?
N41 C42 C43 119.1(3) . . ?
H42 C42 C43 120.4 . . ?
C42 C43 H43 119.7 . . ?
C42 C43 C44 120.5(3) . . ?
H43 C43 C44 119.7 . . ?
C43 C44 H44 119.8 . . ?
C43 C44 C45 120.3(3) . . ?
H44 C44 C45 119.8 . . ?
C44 C45 H45 119.8 . . ?
C44 C45 C46 120.4(3) . . ?
H45 C45 C46 119.8 . . ?
N41 C46 C45 117.6(3) . . ?
N41 C46 N47 110.4(3) . . ?
C45 C46 N47 132.0(3) . . ?
C46 N47 C48 106.2(3) . . ?
N47 C48 C49 110.7(3) . . ?
N47 C48 C50 121.4(3) . . ?
C49 C48 C50 127.9(3) . . ?
N41 C49 C48 106.2(3) . . ?
N41 C49 H49 126.9 . . ?
C48 C49 H49 126.9 . . ?
C48 C50 C51 121.1(3) . . ?
C48 C50 C55 120.2(3) . . ?
C51 C50 C55 118.7(3) . . ?
C50 C51 H51 119.9 . . ?
C50 C51 C52 120.3(4) . . ?
H51 C51 C52 119.9 . . ?
C51 C52 H52 119.5 . . ?
C51 C52 C53 121.1(4) . . ?
H52 C52 C53 119.5 . . ?
C52 C53 H53 120.6 . . ?
C52 C53 C54 118.9(4) . . ?
H53 C53 C54 120.6 . . ?
C53 C54 H54 119.8 . . ?
C53 C54 C55 120.4(4) . . ?
H54 C54 C55 119.8 . . ?
C50 C55 C54 120.6(4) . . ?
C50 C55 H55 119.7 . . ?
C54 C55 H55 119.7 . . ?
C62 N61 C66 123.0(4) . . ?
C62 N61 C69 129.9(4) . . ?
C66 N61 C69 107.1(3) . . ?
N61 C62 H62 120.3 . . ?
N61 C62 C63 119.3(5) . . ?
H62 C62 C63 120.3 . . ?
C62 C63 H63 120.3 . . ?
C62 C63 C64 119.3(4) . . ?
H63 C63 C64 120.3 . . ?
C63 C64 H64 120.4 . . ?
C63 C64 C65 119.1(4) . . ?
H64 C64 C65 120.4 . . ?
C64 C65 H65 119.9 . . ?
C64 C65 C66 120.1(4) . . ?
H65 C65 C66 119.9 . . ?
N61 C66 C65 119.0(4) . . ?
N61 C66 N67 110.7(3) . . ?
C65 C66 N67 130.3(4) . . ?
C66 N67 C68 104.6(3) . . ?
N67 C68 C69 112.6(3) . . ?
N67 C68 C70 120.5(3) . . ?
C69 C68 C70 126.9(4) . . ?
N61 C69 C68 105.1(3) . . ?
N61 C69 H69 127.5 . . ?
C68 C69 H69 127.5 . . ?
C68 C70 C71 122.0(4) . . ?
C68 C70 C75 121.1(4) . . ?
C71 C70 C75 116.8(3) . . ?
C70 C71 H71 120.3 . . ?
C70 C71 C72 119.5(4) . . ?
H71 C71 C72 120.3 . . ?
C71 C72 H72 119.3 . . ?
C71 C72 C73 121.5(4) . . ?
H72 C72 C73 119.3 . . ?
C72 C73 H73 119.9 . . ?
C72 C73 C74 120.2(4) . . ?
H73 C73 C74 119.9 . . ?
C73 C74 H74 119.5 . . ?
C73 C74 C75 120.9(4) . . ?
H74 C74 C75 119.5 . . ?
C70 C75 C74 121.0(4) . . ?
C70 C75 H75 119.5 . . ?
C74 C75 H75 119.5 . . ?

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 N1 C2 C3 0.5(5) . . . . ?
C9 N1 C2 C3 -178.3(3) . . . . ?
N1 C2 C3 C4 -1.9(5) . . . . ?
C2 C3 C4 C5 2.1(6) . . . . ?
C3 C4 C5 C6 -0.7(6) . . . . ?
C4 C5 C6 N1 -0.7(6) . . . . ?
C4 C5 C6 N7 177.7(4) . . . . ?
C2 N1 C6 C5 0.8(5) . . . . ?
C2 N1 C6 N7 -177.9(3) . . . . ?
C9 N1 C6 C5 179.8(3) . . . . ?
C9 N1 C6 N7 1.1(4) . . . . ?
N1 C6 N7 C8 -1.9(4) . . . . ?
C5 C6 N7 C8 179.6(4) . . . . ?
C6 N7 C8 C9 2.1(4) . . . . ?
C6 N7 C8 C10 -179.5(3) . . . . ?
N7 C8 C9 N1 -1.4(4) . . . . ?
C10 C8 C9 N1 -179.7(3) . . . . ?
C2 N1 C9 C8 179.0(3) . . . . ?
C6 N1 C9 C8 0.2(4) . . . . ?
N7 C8 C10 C11 7.4(5) . . . . ?
N7 C8 C10 C15 -173.6(3) . . . . ?
C9 C8 C10 C11 -174.5(3) . . . . ?
C9 C8 C10 C15 4.5(6) . . . . ?
C8 C10 C11 C12 178.5(3) . . . . ?
C15 C10 C11 C12 -0.5(5) . . . . ?
C10 C11 C12 C13 -2.3(5) . . . . ?
C11 C12 C13 C14 2.8(5) . . . . ?
C12 C13 C14 C15 -0.7(6) . . . . ?
C8 C10 C15 C14 -176.3(3) . . . . ?
C11 C10 C15 C14 2.7(6) . . . . ?
C13 C14 C15 C10 -2.1(6) . . . . ?
C26 N21 C22 C23 -1.4(5) . . . . ?
C29 N21 C22 C23 -177.1(4) . . . . ?
N21 C22 C23 C24 -0.4(6) . . . . ?
C22 C23 C24 C25 0.5(6) . . . . ?
C23 C24 C25 C26 1.3(6) . . . . ?
C24 C25 C26 N21 -3.0(5) . . . . ?
C24 C25 C26 N27 176.8(4) . . . . ?
C22 N21 C26 C25 3.1(5) . . . . ?
C22 N21 C26 N27 -176.7(3) . . . . ?
C29 N21 C26 C25 179.7(3) . . . . ?
C29 N21 C26 N27 -0.1(4) . . . . ?
N21 C26 N27 C28 0.2(4) . . . . ?
C25 C26 N27 C28 -179.5(4) . . . . ?
C26 N27 C28 C29 -0.3(4) . . . . ?
C26 N27 C28 C30 179.6(3) . . . . ?
N27 C28 C29 N21 0.3(4) . . . . ?
C30 C28 C29 N21 -179.6(3) . . . . ?
C22 N21 C29 C28 176.0(3) . . . . ?
C26 N21 C29 C28 -0.1(4) . . . . ?
N27 C28 C30 C31 177.1(3) . . . . ?
N27 C28 C30 C35 -4.0(5) . . . . ?
C29 C28 C30 C31 -3.0(6) . . . . ?
C29 C28 C30 C35 175.9(4) . . . . ?
C28 C30 C31 C32 179.0(4) . . . . ?
C35 C30 C31 C32 0.0(6) . . . . ?
C30 C31 C32 C33 -1.2(6) . . . . ?
C31 C32 C33 C34 2.4(6) . . . . ?
C32 C33 C34 C35 -2.5(6) . . . . ?
C33 C34 C35 C30 1.3(6) . . . . ?
C28 C30 C35 C34 -179.1(3) . . . . ?
C31 C30 C35 C34 -0.1(6) . . . . ?
C46 N41 C42 C43 -1.2(5) . . . . ?
C49 N41 C42 C43 177.5(3) . . . . ?
N41 C42 C43 C44 0.9(5) . . . . ?
C42 C43 C44 C45 0.0(5) . . . . ?
C43 C44 C45 C46 -0.7(5) . . . . ?
C44 C45 C46 N41 0.4(5) . . . . ?
C44 C45 C46 N47 -178.3(3) . . . . ?
C42 N41 C46 C45 0.5(4) . . . . ?
C42 N41 C46 N47 179.5(3) . . . . ?
C49 N41 C46 C45 -178.5(3) . . . . ?
C49 N41 C46 N47 0.5(3) . . . . ?
N41 C46 N47 C48 -0.1(4) . . . . ?
C45 C46 N47 C48 178.7(4) . . . . ?
C46 N47 C48 C49 -0.4(4) . . . . ?
C46 N47 C48 C50 -179.9(3) . . . . ?
N47 C48 C49 N41 0.7(4) . . . . ?
C50 C48 C49 N41 -179.9(3) . . . . ?
C42 N41 C49 C48 -179.6(3) . . . . ?
C46 N41 C49 C48 -0.7(3) . . . . ?
N47 C48 C50 C51 169.7(3) . . . . ?
N47 C48 C50 C55 -10.1(5) . . . . ?
C49 C48 C50 C51 -9.7(5) . . . . ?
C49 C48 C50 C55 170.5(3) . . . . ?
C48 C50 C51 C52 179.8(3) . . . . ?
C55 C50 C51 C52 -0.5(5) . . . . ?
C50 C51 C52 C53 0.7(5) . . . . ?
C51 C52 C53 C54 -0.3(5) . . . . ?
C52 C53 C54 C55 -0.3(5) . . . . ?
C48 C50 C55 C54 179.6(3) . . . . ?
C51 C50 C55 C54 -0.2(5) . . . . ?
C53 C54 C55 C50 0.5(5) . . . . ?
C66 N61 C62 C63 2.2(6) . . . . ?
C69 N61 C62 C63 -179.1(4) . . . . ?
N61 C62 C63 C64 -1.5(6) . . . . ?
C62 C63 C64 C65 0.5(6) . . . . ?
C63 C64 C65 C66 -0.2(6) . . . . ?
C62 N61 C66 C65 -1.9(5) . . . . ?
C62 N61 C66 N67 178.1(3) . . . . ?
C69 N61 C66 C65 179.2(3) . . . . ?
C69 N61 C66 N67 -0.9(4) . . . . ?
C64 C65 C66 N61 0.8(6) . . . . ?
C64 C65 C66 N67 -179.1(4) . . . . ?
N61 C66 N67 C68 0.8(4) . . . . ?
C65 C66 N67 C68 -179.3(4) . . . . ?
C66 N67 C68 C69 -0.5(4) . . . . ?
C66 N67 C68 C70 176.8(3) . . . . ?
N67 C68 C69 N61 0.0(4) . . . . ?
C70 C68 C69 N61 -177.1(3) . . . . ?
C62 N61 C69 C68 -178.3(4) . . . . ?
C66 N61 C69 C68 0.5(4) . . . . ?
N67 C68 C70 C71 -176.3(3) . . . . ?
N67 C68 C70 C75 4.1(5) . . . . ?
C69 C68 C70 C71 0.6(6) . . . . ?
C69 C68 C70 C75 -179.0(4) . . . . ?
C68 C70 C71 C72 178.2(3) . . . . ?
C75 C70 C71 C72 -2.1(5) . . . . ?
C70 C71 C72 C73 1.4(6) . . . . ?
C71 C72 C73 C74 -0.4(6) . . . . ?
C72 C73 C74 C75 0.3(6) . . . . ?
C73 C74 C75 C70 -1.1(6) . . . . ?
C68 C70 C75 C74 -178.4(3) . . . . ?
C71 C70 C75 C74 2.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        62.27
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.071

# Contents of RES file
_iucr_refine_instructions_details 
;
TITL mac87 in P2(1)/c
CELL 1.54184 28.7348 5.8963 23.3995 90.000 90.806 90.000
ZERR 16.00 0.0014 0.0002 0.0008 0.000 0.003 0.000
LATT 1
SYMM -x, y+1/2,-z+1/2
SFAC C H N
UNIT 208 160 32

REM colourless lath
SIZE 0.15 0.10 0.01
TEMP -123

L.S. 8
ACTA
BOND $H
CONF
FMAP 2
PLAN 10

REM EXTI 0.000000
WGHT 0.146000 0.625000
FVAR 2.07041
N1 3 0.236450 0.613880 0.594193 11.00000 0.04312 0.05304 =
0.03675 -0.00358 -0.00004 0.01415
C2 1 0.263279 0.782802 0.622735 11.00000 0.04970 0.03634 =
0.05553 0.00020 0.01624 0.00425
AFIX 43
H2 2 0.268780 0.926919 0.605982 11.00000 -1.20000
AFIX 0
C3 1 0.280547 0.728121 0.674847 11.00000 0.04526 0.05131 =
0.04499 -0.01613 -0.00259 0.00079
AFIX 43
H3 2 0.299446 0.834861 0.694828 11.00000 -1.20000
AFIX 0
C4 1 0.271428 0.520165 0.700006 11.00000 0.05899 0.05694 =
0.04440 -0.00228 0.00553 0.00992
AFIX 43
H4 2 0.283381 0.490034 0.737297 11.00000 -1.20000
AFIX 0
C5 1 0.246337 0.361590 0.673219 11.00000 0.06007 0.05096 =
0.04836 -0.00063 0.00610 0.00183
AFIX 43
H5 2 0.240845 0.219776 0.691175 11.00000 -1.20000
AFIX 0
C6 1 0.228568 0.403575 0.619935 11.00000 0.04371 0.02796 =
0.05536 -0.00493 0.00755 0.00196
N7 3 0.203420 0.273436 0.582462 11.00000 0.05853 0.03580 =
0.04713 0.00765 0.00655 0.00154
C8 1 0.195219 0.407323 0.535831 11.00000 0.03928 0.02626 =
0.03757 0.00494 0.00339 0.00402
C9 1 0.215506 0.616179 0.541062 11.00000 0.05507 0.03599 =
0.04813 0.00489 0.00527 0.00683
AFIX 43
H9 2 0.215188 0.736203 0.513974 11.00000 -1.20000
AFIX 0
C10 1 0.167733 0.319577 0.485282 11.00000 0.03965 0.03740 =
0.05351 -0.00629 0.01094 0.00222
C11 1 0.146454 0.110928 0.489644 11.00000 0.05276 0.05269 =
0.03892 0.01317 0.00569 0.01956
AFIX 43
H11 2 0.149972 0.024691 0.523726 11.00000 -1.20000
AFIX 0
C12 1 0.119118 0.023748 0.443115 11.00000 0.04956 0.03474 =
0.07275 0.00385 0.01225 0.00220
AFIX 43
H12 2 0.105271 -0.122246 0.445290 11.00000 -1.20000
AFIX 0
C13 1 0.113265 0.156953 0.394757 11.00000 0.04407 0.05290 =
0.04126 -0.01103 -0.00536 0.01121
AFIX 43
H13 2 0.094188 0.107332 0.363715 11.00000 -1.20000
AFIX 0
C14 1 0.135646 0.361932 0.392780 11.00000 0.04777 0.04866 =
0.05085 0.00855 -0.00500 0.00305
AFIX 43
H14 2 0.132121 0.453497 0.359596 11.00000 -1.20000
AFIX 0
C15 1 0.162738 0.438422 0.436809 11.00000 0.04833 0.04484 =
0.05993 0.00040 0.00279 0.00197
AFIX 43
H15 2 0.178470 0.579255 0.433110 11.00000 -1.20000
AFIX 0
N21 3 0.519337 0.428953 0.617673 11.00000 0.04196 0.03176 =
0.04107 -0.00120 -0.00601 -0.00353
C22 1 0.556505 0.362335 0.584382 11.00000 0.04347 0.03743 =
0.06170 -0.01615 -0.01039 0.01269
AFIX 43
H22 2 0.571276 0.220164 0.590627 11.00000 -1.20000
AFIX 0
C23 1 0.571295 0.503336 0.542934 11.00000 0.04478 0.05509 =
0.04700 -0.01410 0.00545 0.00136
AFIX 43
H23 2 0.596842 0.460639 0.519956 11.00000 -1.20000
AFIX 0
C24 1 0.549010 0.714002 0.533527 11.00000 0.05185 0.05163 =
0.04710 0.00519 0.00119 0.00186
AFIX 43
H24 2 0.559544 0.811353 0.504058 11.00000 -1.20000
AFIX 0
C25 1 0.513071 0.777711 0.565896 11.00000 0.04962 0.04009 =
0.04910 0.00390 -0.00414 0.00375
AFIX 43
H25 2 0.497987 0.918365 0.558629 11.00000 -1.20000
AFIX 0
C26 1 0.497747 0.639531 0.609963 11.00000 0.03546 0.02795 =
0.04488 -0.00219 -0.00362 0.00383
N27 3 0.464658 0.671385 0.648565 11.00000 0.04029 0.02758 =
0.04708 0.00498 -0.00407 0.00203
C28 1 0.465455 0.478511 0.681324 11.00000 0.03770 0.02465 =
0.04059 0.00021 -0.01207 0.00005
C29 1 0.498335 0.328766 0.663162 11.00000 0.04372 0.02515 =
0.05276 0.00061 -0.01016 0.00448
AFIX 43
H29 2 0.505214 0.184025 0.678988 11.00000 -1.20000
AFIX 0
C30 1 0.433019 0.453804 0.729622 11.00000 0.03378 0.03651 =
0.04049 -0.00220 -0.00971 -0.00441
C31 1 0.431439 0.257557 0.761916 11.00000 0.04888 0.04249 =
0.05605 0.00603 -0.00764 0.00506
AFIX 43
H31 2 0.451197 0.133948 0.752797 11.00000 -1.20000
AFIX 0
C32 1 0.401315 0.239358 0.807464 11.00000 0.05965 0.05365 =
0.05317 0.01793 -0.00980 -0.00515
AFIX 43
H32 2 0.400230 0.102339 0.828763 11.00000 -1.20000
AFIX 0
C33 1 0.373181 0.416273 0.822048 11.00000 0.05294 0.06785 =
0.03589 0.00022 -0.00224 -0.01417
AFIX 43
H33 2 0.353482 0.404784 0.854186 11.00000 -1.20000
AFIX 0
C34 1 0.373644 0.614087 0.789294 11.00000 0.04712 0.05636 =
0.05397 -0.01578 -0.00309 0.00316
AFIX 43
H34 2 0.353361 0.736029 0.798102 11.00000 -1.20000
AFIX 0
C35 1 0.403776 0.631597 0.743968 11.00000 0.05728 0.03863 =
0.04572 0.00832 -0.00393 -0.01038
AFIX 43
H35 2 0.404476 0.767693 0.722267 11.00000 -1.20000
AFIX 0
N41 3 0.324265 1.151546 0.521183 11.00000 0.03451 0.02926 =
0.03423 0.00254 0.00303 0.00302
C42 1 0.333467 1.325421 0.559506 11.00000 0.03903 0.02899 =
0.04526 0.00082 0.00764 0.00602
AFIX 43
H42 2 0.317894 1.466916 0.555862 11.00000 -1.20000
AFIX 0
C43 1 0.364671 1.291394 0.601855 11.00000 0.04019 0.03226 =
0.04217 -0.00173 0.00170 -0.00039
AFIX 43
H43 2 0.370885 1.408927 0.628664 11.00000 -1.20000
AFIX 0
C44 1 0.388401 1.081810 0.606903 11.00000 0.03813 0.03773 =
0.03788 0.00446 -0.00412 -0.00103
AFIX 43
H44 2 0.410412 1.059565 0.637057 11.00000 -1.20000
AFIX 0
C45 1 0.379870 0.912427 0.568878 11.00000 0.04025 0.03145 =
0.04531 0.00196 -0.00261 0.00357
AFIX 43
H45 2 0.396200 0.772891 0.572318 11.00000 -1.20000
AFIX 0
C46 1 0.347176 0.942192 0.524668 11.00000 0.03898 0.02423 =
0.03781 0.00210 0.00510 0.00368
N47 3 0.331940 0.803508 0.483361 11.00000 0.04518 0.02421 =
0.03993 0.00346 -0.00149 0.00478
C48 1 0.298872 0.923290 0.452868 11.00000 0.03446 0.03135 =
0.03537 0.00664 0.00401 0.00365
C49 1 0.293290 1.136453 0.475453 11.00000 0.03792 0.03157 =
0.03937 0.00878 0.00233 0.00687
AFIX 43
H49 2 0.272387 1.250572 0.462341 11.00000 -1.20000
AFIX 0
C50 1 0.274190 0.822103 0.403498 11.00000 0.04189 0.03189 =
0.03362 0.00540 0.00400 -0.00097
C51 1 0.235945 0.928639 0.378545 11.00000 0.04457 0.04372 =
0.03557 0.00177 0.00211 0.00485
AFIX 43
H51 2 0.225280 1.068969 0.393408 11.00000 -1.20000
AFIX 0
C52 1 0.213203 0.831041 0.331959 11.00000 0.04643 0.05552 =
0.04000 0.00912 -0.00413 0.00068
AFIX 43
H52 2 0.187276 0.906512 0.314984 11.00000 -1.20000
AFIX 0
C53 1 0.227700 0.625400 0.309821 11.00000 0.05067 0.05643 =
0.03256 0.00541 -0.00103 -0.00866
AFIX 43
H53 2 0.211848 0.559329 0.278047 11.00000 -1.20000
AFIX 0
C54 1 0.265456 0.518349 0.334621 11.00000 0.05733 0.03831 =
0.04314 -0.00259 0.00860 0.00064
AFIX 43
H54 2 0.275696 0.376866 0.319993 11.00000 -1.20000
AFIX 0
C55 1 0.288849 0.616703 0.381259 11.00000 0.04565 0.03549 =
0.04201 0.00625 0.00064 0.00137
AFIX 43
H55 2 0.315031 0.541962 0.397837 11.00000 -1.20000
AFIX 0
N61 3 -0.008660 1.045305 0.863697 11.00000 0.04369 0.05066 =
0.04828 -0.00391 -0.00719 -0.01173
C62 1 -0.042026 1.147418 0.894208 11.00000 0.06100 0.04967 =
0.05748 -0.01349 -0.01215 -0.00044
AFIX 43
H62 2 -0.054241 1.289926 0.882429 11.00000 -1.20000
AFIX 0
C63 1 -0.058019 1.045051 0.941864 11.00000 0.04502 0.10586 =
0.06360 -0.04215 -0.00172 0.00213
AFIX 43
H63 2 -0.081038 1.116650 0.964356 11.00000 -1.20000
AFIX 0
C64 1 -0.039597 0.824386 0.958259 11.00000 0.05562 0.09613 =
0.04213 0.00920 -0.00394 -0.03397
AFIX 43
H64 2 -0.050619 0.749556 0.991379 11.00000 -1.20000
AFIX 0
C65 1 -0.006650 0.727308 0.925828 11.00000 0.05774 0.04834 =
0.06074 0.00236 -0.01393 -0.00883
AFIX 43
H65 2 0.005735 0.583430 0.936171 11.00000 -1.20000
AFIX 0
C66 1 0.009169 0.837051 0.877446 11.00000 0.04081 0.04745 =
0.04676 -0.00483 -0.00628 -0.00995
N67 3 0.041010 0.771867 0.838796 11.00000 0.04947 0.03596 =
0.06011 0.00886 -0.01165 -0.00524
C68 1 0.042911 0.946113 0.801259 11.00000 0.04264 0.02733 =
0.05291 0.00365 -0.02145 -0.00268
C69 1 0.013383 1.116630 0.814515 11.00000 0.05362 0.03703 =
0.05337 0.00597 -0.01250 -0.00912
AFIX 43
H69 2 0.008772 1.255095 0.794465 11.00000 -1.20000
AFIX 0
C70 1 0.076517 0.941526 0.753349 11.00000 0.03510 0.06324 =
0.03562 -0.00308 -0.00699 -0.01865
C71 1 0.081325 1.124206 0.715698 11.00000 0.05252 0.03605 =
0.06730 -0.00627 -0.01918 0.00515
AFIX 43
H71 2 0.062299 1.254966 0.719473 11.00000 -1.20000
AFIX 0
C72 1 0.114402 1.112682 0.672425 11.00000 0.06099 0.05468 =
0.05033 0.01714 -0.00693 -0.02226
AFIX 43
H72 2 0.118076 1.238346 0.647483 11.00000 -1.20000
AFIX 0
C73 1 0.140780 0.929809 0.665464 11.00000 0.04748 0.06712 =
0.05088 -0.00102 -0.00317 -0.00443
AFIX 43
H73 2 0.162831 0.925661 0.635611 11.00000 -1.20000
AFIX 0
C74 1 0.136311 0.748922 0.700880 11.00000 0.04798 0.05103 =
0.06277 -0.00633 -0.00633 0.00897
AFIX 43
H74 2 0.155429 0.619345 0.695628 11.00000 -1.20000
AFIX 0
C75 1 0.104886 0.750625 0.743721 11.00000 0.05343 0.03649 =
0.04933 0.01555 -0.01431 -0.00787
AFIX 43
H75 2 0.101983 0.621133 0.767564 11.00000 -1.20000

HKLF 4

REM mac87 in P2(1)/c
REM R1 = 0.0784 for 4212 Fo > 4sig(Fo) and 0.1073 for all 6140 data
REM 541 parameters refined using 0 restraints

END

;
_database_code_depnum_ccdc_archive 'CCDC 907271'
#######################################################################
#
#                 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_mac68_3a.HCl.H2O
#TrackingRef '14897_web_deposit_cif_file_0_BillClegg_1351029791.combined.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N2 +,Cl -,H2 O'
_chemical_formula_sum            'C13 H13 Cl N2 O'
_chemical_formula_weight         248.70

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'
Cl Cl 0.1484 0.1585 '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           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   6.8922(4)
_cell_length_b                   9.1653(6)
_cell_length_c                   10.6422(6)
_cell_angle_alpha                74.573(5)
_cell_angle_beta                 74.634(5)
_cell_angle_gamma                71.501(5)
_cell_volume                     602.44(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6311
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      27.96

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             260
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube with Enhance optics'
_diffrn_radiation_monochromator  none
_diffrn_measurement_device_type  
'Oxford Diffraction Gemini A Ultra diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.3968
_diffrn_reflns_number            9325
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         28.02
_reflns_number_total             2571
_reflns_number_gt                2116
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
;
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'

_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^)+(0.0462P)^2^+0.2544P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2571
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0948
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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 0.2984(2) 0.24512(15) 0.70697(13) 0.0217(3) Uani 1 1 d . . .
C2 C 0.3149(3) 0.10594(19) 0.79873(17) 0.0272(4) Uani 1 1 d . . .
H2 H 0.3528 0.0084 0.7713 0.033 Uiso 1 1 calc R . .
C3 C 0.2756(3) 0.1121(2) 0.92928(17) 0.0296(4) Uani 1 1 d . . .
H3 H 0.2847 0.0176 0.9943 0.036 Uiso 1 1 calc R . .
C4 C 0.2215(3) 0.2569(2) 0.97008(16) 0.0278(4) Uani 1 1 d . . .
H4 H 0.1953 0.2586 1.0620 0.033 Uiso 1 1 calc R . .
C5 C 0.2064(2) 0.39422(19) 0.87877(16) 0.0235(3) Uani 1 1 d . . .
H5 H 0.1715 0.4920 0.9053 0.030(5) Uiso 1 1 calc R . .
C6 C 0.2438(2) 0.38613(17) 0.74511(15) 0.0180(3) Uani 1 1 d . . .
N7 N 0.2319(2) 0.49929(15) 0.63510(13) 0.0197(3) Uani 1 1 d . . .
H7 H 0.201(3) 0.604(3) 0.637(2) 0.034(5) Uiso 1 1 d . . .
C8 C 0.2782(2) 0.43095(17) 0.52594(15) 0.0180(3) Uani 1 1 d . . .
C9 C 0.3205(2) 0.27295(18) 0.57065(15) 0.0194(3) Uani 1 1 d . . .
H9 H 0.346(3) 0.201(2) 0.5278(19) 0.028(5) Uiso 1 1 d . . .
C10 C 0.2726(2) 0.51903(17) 0.38991(15) 0.0183(3) Uani 1 1 d . . .
C11 C 0.3283(2) 0.43732(19) 0.28631(16) 0.0232(3) Uani 1 1 d . . .
H11 H 0.3718 0.3258 0.3044 0.028 Uiso 1 1 calc R . .
C12 C 0.3198(3) 0.5189(2) 0.15775(16) 0.0270(4) Uani 1 1 d . . .
H12 H 0.3583 0.4630 0.0876 0.032 Uiso 1 1 calc R . .
C13 C 0.2558(3) 0.6818(2) 0.12973(17) 0.0278(4) Uani 1 1 d . . .
H13 H 0.2494 0.7370 0.0411 0.033 Uiso 1 1 calc R . .
C14 C 0.2015(3) 0.7632(2) 0.23183(17) 0.0272(4) Uani 1 1 d . . .
H14 H 0.1585 0.8747 0.2130 0.033 Uiso 1 1 calc R . .
C15 C 0.2095(2) 0.68264(18) 0.36145(16) 0.0233(3) Uani 1 1 d . . .
H15 H 0.1718 0.7392 0.4311 0.028 Uiso 1 1 calc R . .
Cl16 Cl 0.12712(7) 0.82702(5) 0.70427(5) 0.03662(15) Uani 1 1 d . . .
O17 O -0.2874(2) 0.96891(18) 0.58208(18) 0.0419(4) Uani 1 1 d . . .
H17A H -0.251(4) 1.021(3) 0.509(3) 0.053(8) Uiso 1 1 d . . .
H17B H -0.180(5) 0.925(4) 0.615(3) 0.076(10) Uiso 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 0.0223(7) 0.0215(7) 0.0215(7) -0.0044(5) -0.0027(5) -0.0074(5)
C2 0.0308(9) 0.0198(8) 0.0292(9) -0.0005(6) -0.0061(7) -0.0078(7)
C3 0.0333(9) 0.0292(9) 0.0247(9) 0.0037(7) -0.0064(7) -0.0130(7)
C4 0.0271(8) 0.0377(9) 0.0193(8) -0.0035(7) -0.0036(7) -0.0119(7)
C5 0.0214(8) 0.0300(9) 0.0209(8) -0.0087(6) -0.0020(6) -0.0080(6)
C6 0.0143(7) 0.0201(7) 0.0199(7) -0.0042(6) -0.0022(6) -0.0059(6)
N7 0.0202(6) 0.0190(7) 0.0206(7) -0.0062(5) -0.0027(5) -0.0052(5)
C8 0.0152(7) 0.0214(7) 0.0192(7) -0.0074(6) -0.0017(6) -0.0057(6)
C9 0.0225(8) 0.0193(7) 0.0176(7) -0.0070(6) -0.0018(6) -0.0062(6)
C10 0.0139(7) 0.0223(8) 0.0191(7) -0.0047(6) -0.0018(6) -0.0061(6)
C11 0.0238(8) 0.0244(8) 0.0232(8) -0.0065(6) -0.0041(6) -0.0077(6)
C12 0.0284(9) 0.0357(9) 0.0210(8) -0.0087(7) -0.0034(7) -0.0130(7)
C13 0.0260(8) 0.0353(9) 0.0219(8) 0.0017(7) -0.0058(7) -0.0129(7)
C14 0.0261(8) 0.0240(8) 0.0276(9) -0.0004(7) -0.0044(7) -0.0061(7)
C15 0.0234(8) 0.0225(8) 0.0229(8) -0.0065(6) -0.0010(6) -0.0059(6)
Cl16 0.0417(3) 0.0261(2) 0.0392(3) -0.00644(18) -0.0048(2) -0.00772(18)
O17 0.0361(8) 0.0372(8) 0.0493(10) -0.0047(7) -0.0043(7) -0.0122(7)

_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 C2 1.378(2) . ?
N1 C6 1.3661(19) . ?
N1 C9 1.380(2) . ?
C2 H2 0.950 . ?
C2 C3 1.356(2) . ?
C3 H3 0.950 . ?
C3 C4 1.412(2) . ?
C4 H4 0.950 . ?
C4 C5 1.364(2) . ?
C5 H5 0.950 . ?
C5 C6 1.395(2) . ?
C6 N7 1.343(2) . ?
N7 H7 0.92(2) . ?
N7 C8 1.3811(19) . ?
C8 C9 1.359(2) . ?
C8 C10 1.462(2) . ?
C9 H9 0.85(2) . ?
C10 C11 1.399(2) . ?
C10 C15 1.394(2) . ?
C11 H11 0.950 . ?
C11 C12 1.380(2) . ?
C12 H12 0.950 . ?
C12 C13 1.388(2) . ?
C13 H13 0.950 . ?
C13 C14 1.384(2) . ?
C14 H14 0.950 . ?
C14 C15 1.387(2) . ?
C15 H15 0.950 . ?
O17 H17A 0.82(3) . ?
O17 H17B 0.84(3) . ?

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 N1 C6 121.49(13) . . ?
C2 N1 C9 130.05(14) . . ?
C6 N1 C9 108.40(13) . . ?
N1 C2 H2 120.9 . . ?
N1 C2 C3 118.12(15) . . ?
H2 C2 C3 120.9 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.02(16) . . ?
H3 C3 C4 119.5 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.61(15) . . ?
H4 C4 C5 119.7 . . ?
C4 C5 H5 121.2 . . ?
C4 C5 C6 117.68(15) . . ?
H5 C5 C6 121.2 . . ?
N1 C6 C5 121.07(14) . . ?
N1 C6 N7 107.63(13) . . ?
C5 C6 N7 131.28(14) . . ?
C6 N7 H7 122.5(13) . . ?
C6 N7 C8 109.08(13) . . ?
H7 N7 C8 128.4(13) . . ?
N7 C8 C9 107.40(13) . . ?
N7 C8 C10 124.18(13) . . ?
C9 C8 C10 128.38(14) . . ?
N1 C9 C8 107.48(13) . . ?
N1 C9 H9 123.2(13) . . ?
C8 C9 H9 129.1(13) . . ?
C8 C10 C11 119.27(14) . . ?
C8 C10 C15 121.46(14) . . ?
C11 C10 C15 119.26(14) . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.89(15) . . ?
H11 C11 C12 120.1 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.75(15) . . ?
H12 C12 C13 119.6 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.57(15) . . ?
H13 C13 C14 120.2 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.25(15) . . ?
H14 C14 C15 119.9 . . ?
C10 C15 C14 120.27(15) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
H17A O17 H17B 107(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 N1 C2 C3 -0.1(2) . . . . ?
C9 N1 C2 C3 -176.89(16) . . . . ?
N1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C2 N1 C6 C5 1.2(2) . . . . ?
C2 N1 C6 N7 -177.34(13) . . . . ?
C9 N1 C6 C5 178.60(14) . . . . ?
C9 N1 C6 N7 0.08(16) . . . . ?
C4 C5 C6 N1 -1.5(2) . . . . ?
C4 C5 C6 N7 176.66(15) . . . . ?
N1 C6 N7 C8 0.21(16) . . . . ?
C5 C6 N7 C8 -178.10(15) . . . . ?
C6 N7 C8 C9 -0.43(16) . . . . ?
C6 N7 C8 C10 177.57(13) . . . . ?
N7 C8 C9 N1 0.47(17) . . . . ?
C10 C8 C9 N1 -177.41(14) . . . . ?
C2 N1 C9 C8 176.78(15) . . . . ?
C6 N1 C9 C8 -0.35(17) . . . . ?
N7 C8 C10 C11 178.21(14) . . . . ?
N7 C8 C10 C15 -2.9(2) . . . . ?
C9 C8 C10 C11 -4.2(2) . . . . ?
C9 C8 C10 C15 174.62(15) . . . . ?
C8 C10 C11 C12 178.75(14) . . . . ?
C15 C10 C11 C12 -0.1(2) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C14 C15 C10 0.1(2) . . . . ?
C8 C10 C15 C14 -178.66(14) . . . . ?
C11 C10 C15 C14 0.2(2) . . . . ?

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
N7 H7 Cl16 0.92(2) 2.21(2) 3.0991(14) 163.4(17) .
O17 H17A Cl16 0.82(3) 2.42(3) 3.2404(18) 177(2) 2_576
O17 H17B Cl16 0.84(3) 2.36(3) 3.2024(18) 174(3) .

_diffrn_measured_fraction_theta_max 0.881
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.045

# Contents of RES file
_iucr_refine_instructions_details 
;
TITL mac68 in P-1
CELL 0.71073 6.8922 9.1653 10.6422 74.573 74.634 71.501
ZERR 2.00 0.0004 0.0006 0.0006 0.005 0.005 0.005
LATT 1
SFAC C H N Cl O
UNIT 26 26 4 2 2

REM colourless block
SIZE 0.30 0.20 0.20
TEMP -123

L.S. 8
ACTA 52
BOND $H
CONF
FMAP 2
PLAN 10

EQIV $1 -X, -Y+2, -Z+1
HTAB N7 CL16
HTAB O17 CL16_$1
HTAB O17 CL16

REM EXTI 0.000000
WGHT 0.046200 0.254400
FVAR 0.77955
N1 3 0.298373 0.245121 0.706968 11.00000 0.02228 0.02150 =
0.02150 -0.00437 -0.00275 -0.00741
C2 1 0.314930 0.105938 0.798732 11.00000 0.03080 0.01981 =
0.02915 -0.00050 -0.00612 -0.00785
AFIX 43
H2 2 0.352787 0.008401 0.771343 11.00000 -1.20000
AFIX 0
C3 1 0.275650 0.112110 0.929281 11.00000 0.03335 0.02915 =
0.02466 0.00370 -0.00636 -0.01302
AFIX 43
H3 2 0.284717 0.017600 0.994279 11.00000 -1.20000
AFIX 0
C4 1 0.221473 0.256879 0.970082 11.00000 0.02711 0.03766 =
0.01930 -0.00355 -0.00362 -0.01187
AFIX 43
H4 2 0.195321 0.258589 1.061997 11.00000 -1.20000
AFIX 0
C5 1 0.206356 0.394219 0.878768 11.00000 0.02141 0.02996 =
0.02093 -0.00871 -0.00198 -0.00799
AFIX 43
H5 2 0.171533 0.492002 0.905275 11.00000 0.03015
AFIX 0
C6 1 0.243799 0.386126 0.745113 11.00000 0.01432 0.02008 =
0.01989 -0.00418 -0.00224 -0.00591
N7 3 0.231874 0.499288 0.635098 11.00000 0.02018 0.01897 =
0.02060 -0.00615 -0.00268 -0.00517
H7 2 0.200932 0.603602 0.637289 11.00000 0.03439
C8 1 0.278167 0.430949 0.525942 11.00000 0.01519 0.02137 =
0.01919 -0.00736 -0.00167 -0.00572
C9 1 0.320476 0.272949 0.570652 11.00000 0.02251 0.01932 =
0.01759 -0.00702 -0.00179 -0.00619
H9 2 0.345782 0.200961 0.527767 11.00000 0.02787
C10 1 0.272582 0.519035 0.389912 11.00000 0.01389 0.02227 =
0.01914 -0.00471 -0.00184 -0.00611
C11 1 0.328265 0.437316 0.286315 11.00000 0.02378 0.02436 =
0.02324 -0.00648 -0.00408 -0.00770
AFIX 43
H11 2 0.371811 0.325835 0.304420 11.00000 -1.20000
AFIX 0
C12 1 0.319844 0.518901 0.157747 11.00000 0.02837 0.03569 =
0.02102 -0.00867 -0.00335 -0.01300
AFIX 43
H12 2 0.358292 0.462956 0.087630 11.00000 -1.20000
AFIX 0
C13 1 0.255834 0.681772 0.129725 11.00000 0.02601 0.03532 =
0.02187 0.00172 -0.00577 -0.01295
AFIX 43
H13 2 0.249382 0.736997 0.041054 11.00000 -1.20000
AFIX 0
C14 1 0.201463 0.763203 0.231832 11.00000 0.02614 0.02400 =
0.02764 -0.00035 -0.00443 -0.00615
AFIX 43
H14 2 0.158515 0.874694 0.213047 11.00000 -1.20000
AFIX 0
C15 1 0.209450 0.682639 0.361451 11.00000 0.02336 0.02252 =
0.02286 -0.00653 -0.00104 -0.00593
AFIX 43
H15 2 0.171751 0.739166 0.431121 11.00000 -1.20000
AFIX 0
CL16 4 0.127122 0.827016 0.704275 11.00000 0.04167 0.02607 =
0.03923 -0.00644 -0.00477 -0.00772
O17 5 -0.287376 0.968907 0.582082 11.00000 0.03611 0.03722 =
0.04933 -0.00469 -0.00434 -0.01218
H17A 2 -0.251016 1.021483 0.508752 11.00000 0.05317
H17B 2 -0.179540 0.925258 0.614762 11.00000 0.07587

HKLF 4

REM mac68 in P-1
REM R1 = 0.0350 for 2116 Fo > 4sig(Fo) and 0.0446 for all 2571 data
REM 171 parameters refined using 0 restraints

END

;
_database_code_depnum_ccdc_archive 'CCDC 907272'
#######################################################################
#
#                 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_mac67_4a.HCl.2H2O
#TrackingRef '14897_web_deposit_cif_file_0_BillClegg_1351029791.combined.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N2 +,Cl -,2 H2 O'
_chemical_formula_sum            'C13 H15 Cl N2 O2'
_chemical_formula_weight         266.72

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'
Cl Cl 0.1484 0.1585 '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           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                   11.2615(9)
_cell_length_b                   7.2071(6)
_cell_length_c                   16.8121(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.751(8)
_cell_angle_gamma                90.00
_cell_volume                     1335.92(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3286
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      29.45

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube with Enhance optics'
_diffrn_radiation_monochromator  none
_diffrn_measurement_device_type  
'Oxford Diffraction Gemini A Ultra diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.3968
_diffrn_reflns_number            7628
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0536
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         29.52
_reflns_number_total             3170
_reflns_number_gt                2167
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET)
(compiled Feb 27 2009,15:38:38)
;
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'

_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^)+(0.0507P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3170
_refine_ls_number_parameters     178
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1002
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.043
_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
N1 N 0.56504(11) 0.2690(2) 0.26833(9) 0.0189(3) Uani 1 1 d . . .
C2 C 0.56838(16) 0.1967(3) 0.34455(11) 0.0234(4) Uani 1 1 d . . .
H2 H 0.6436 0.1799 0.3814 0.028 Uiso 1 1 calc R . .
C3 C 0.46332(16) 0.1500(3) 0.36619(12) 0.0268(4) Uani 1 1 d . . .
H3 H 0.4647 0.1025 0.4191 0.032 Uiso 1 1 calc R . .
C4 C 0.35171(16) 0.1711(3) 0.31128(12) 0.0288(4) Uani 1 1 d . . .
H4 H 0.2785 0.1386 0.3276 0.035 Uiso 1 1 calc R . .
C5 C 0.34761(15) 0.2377(3) 0.23473(12) 0.0271(4) Uani 1 1 d . . .
H5 H 0.2728 0.2498 0.1969 0.033 Uiso 1 1 calc R . .
C6 C 0.45704(15) 0.2874(2) 0.21400(11) 0.0214(4) Uani 1 1 d . . .
N7 N 0.48285(13) 0.3516(2) 0.14452(9) 0.0239(4) Uani 1 1 d D . .
H7 H 0.4278(14) 0.390(3) 0.1039(9) 0.029 Uiso 1 1 d D . .
C8 C 0.60505(15) 0.3763(3) 0.15402(11) 0.0233(4) Uani 1 1 d . . .
H8 H 0.6455 0.4217 0.1136 0.028 Uiso 1 1 calc R . .
C9 C 0.65952(14) 0.3256(2) 0.23035(10) 0.0198(4) Uani 1 1 d . . .
C10 C 0.78802(15) 0.3256(2) 0.27038(11) 0.0201(4) Uani 1 1 d . . .
C11 C 0.87323(15) 0.2733(2) 0.22442(11) 0.0234(4) Uani 1 1 d . . .
H11 H 0.8469 0.2359 0.1695 0.028 Uiso 1 1 calc R . .
C12 C 0.99571(15) 0.2760(3) 0.25896(12) 0.0294(5) Uani 1 1 d . . .
H12 H 1.0533 0.2418 0.2274 0.035 Uiso 1 1 calc R . .
C13 C 1.03461(16) 0.3280(3) 0.33887(13) 0.0325(5) Uani 1 1 d . . .
H13 H 1.1188 0.3290 0.3624 0.039 Uiso 1 1 calc R . .
C14 C 0.95106(16) 0.3786(3) 0.38473(12) 0.0306(5) Uani 1 1 d . . .
H14 H 0.9780 0.4121 0.4401 0.037 Uiso 1 1 calc R . .
C15 C 0.82810(16) 0.3809(3) 0.35050(11) 0.0253(4) Uani 1 1 d . . .
H15 H 0.7714 0.4203 0.3818 0.030 Uiso 1 1 calc R . .
Cl16 Cl 0.26329(4) 0.48186(7) 0.01601(3) 0.02627(14) Uani 1 1 d . . .
O17 O 0.14042(15) 0.8769(2) -0.02956(10) 0.0459(4) Uani 1 1 d D . .
H17A H 0.185(2) 0.790(3) -0.0053(14) 0.069 Uiso 1 1 d D . .
H17B H 0.133(2) 0.953(3) 0.0089(12) 0.069 Uiso 1 1 d D . .
O18 O 0.11147(14) 0.1579(2) 0.07810(10) 0.0479(4) Uani 1 1 d D . .
H18A H 0.131(2) 0.248(3) 0.0517(15) 0.072 Uiso 1 1 d D . .
H18B H 0.0337(10) 0.143(4) 0.0658(16) 0.072 Uiso 1 1 d 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 0.0192(7) 0.0204(8) 0.0174(7) 0.0026(6) 0.0047(5) 0.0029(6)
C2 0.0260(9) 0.0253(10) 0.0186(9) 0.0021(8) 0.0035(7) 0.0029(8)
C3 0.0311(10) 0.0292(11) 0.0224(10) 0.0026(8) 0.0109(8) 0.0020(8)
C4 0.0255(9) 0.0310(11) 0.0337(11) -0.0020(9) 0.0151(8) 0.0015(8)
C5 0.0202(9) 0.0294(11) 0.0309(11) 0.0001(9) 0.0034(7) 0.0040(8)
C6 0.0217(8) 0.0212(9) 0.0205(10) 0.0005(7) 0.0028(7) 0.0042(7)
N7 0.0227(8) 0.0261(9) 0.0212(8) 0.0047(7) 0.0007(6) 0.0036(6)
C8 0.0272(9) 0.0219(10) 0.0219(9) 0.0013(8) 0.0078(7) -0.0005(7)
C9 0.0210(8) 0.0200(9) 0.0199(9) 0.0011(7) 0.0078(7) 0.0017(7)
C10 0.0214(8) 0.0160(9) 0.0234(9) 0.0016(7) 0.0057(7) -0.0004(7)
C11 0.0271(9) 0.0214(10) 0.0232(10) 0.0026(8) 0.0087(7) 0.0002(8)
C12 0.0247(9) 0.0276(11) 0.0396(12) 0.0030(9) 0.0150(8) 0.0010(8)
C13 0.0206(9) 0.0284(11) 0.0463(13) 0.0012(10) 0.0013(8) -0.0008(8)
C14 0.0284(10) 0.0327(11) 0.0273(11) -0.0046(9) -0.0023(8) -0.0015(8)
C15 0.0253(9) 0.0248(10) 0.0261(10) -0.0018(8) 0.0058(7) 0.0031(8)
Cl16 0.0237(2) 0.0340(3) 0.0197(2) 0.0003(2) 0.00116(15) 0.00173(19)
O17 0.0548(10) 0.0425(10) 0.0433(10) 0.0010(8) 0.0168(8) 0.0042(8)
O18 0.0469(9) 0.0529(11) 0.0424(10) -0.0002(8) 0.0054(8) -0.0064(8)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.377(2) . ?
N1 C6 1.371(2) . ?
N1 C9 1.408(2) . ?
C2 H2 0.950 . ?
C2 C3 1.349(2) . ?
C3 H3 0.950 . ?
C3 C4 1.408(3) . ?
C4 H4 0.950 . ?
C4 C5 1.366(3) . ?
C5 H5 0.950 . ?
C5 C6 1.394(2) . ?
C6 N7 1.342(2) . ?
N7 H7 0.869(9) . ?
N7 C8 1.364(2) . ?
C8 H8 0.950 . ?
C8 C9 1.355(2) . ?
C9 C10 1.466(2) . ?
C10 C11 1.401(2) . ?
C10 C15 1.389(3) . ?
C11 H11 0.950 . ?
C11 C12 1.383(2) . ?
C12 H12 0.950 . ?
C12 C13 1.378(3) . ?
C13 H13 0.950 . ?
C13 C14 1.381(3) . ?
C14 H14 0.950 . ?
C14 C15 1.387(3) . ?
C15 H15 0.950 . ?
O17 H17A 0.854(10) . ?
O17 H17B 0.866(10) . ?
O18 H18A 0.841(10) . ?
O18 H18B 0.865(9) . ?

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 N1 C6 120.62(14) . . ?
C2 N1 C9 130.68(14) . . ?
C6 N1 C9 108.64(14) . . ?
N1 C2 H2 120.5 . . ?
N1 C2 C3 119.08(16) . . ?
H2 C2 C3 120.5 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.74(18) . . ?
H3 C3 C4 119.6 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.67(17) . . ?
H4 C4 C5 119.7 . . ?
C4 C5 H5 121.2 . . ?
C4 C5 C6 117.64(16) . . ?
H5 C5 C6 121.2 . . ?
N1 C6 C5 121.21(16) . . ?
N1 C6 N7 107.06(14) . . ?
C5 C6 N7 131.71(16) . . ?
C6 N7 H7 123.2(13) . . ?
C6 N7 C8 109.58(15) . . ?
H7 N7 C8 126.3(13) . . ?
N7 C8 H8 125.5 . . ?
N7 C8 C9 109.09(16) . . ?
H8 C8 C9 125.5 . . ?
N1 C9 C8 105.63(14) . . ?
N1 C9 C10 123.92(15) . . ?
C8 C9 C10 130.45(16) . . ?
C9 C10 C11 118.02(16) . . ?
C9 C10 C15 122.71(15) . . ?
C11 C10 C15 119.23(15) . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.08(17) . . ?
H11 C11 C12 120.0 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.34(17) . . ?
H12 C12 C13 119.8 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 119.91(17) . . ?
H13 C13 C14 120.0 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.49(18) . . ?
H14 C14 C15 119.8 . . ?
C10 C15 C14 119.91(17) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
H17A O17 H17B 104.4(19) . . ?
H18A O18 H18B 109.6(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
C6 N1 C2 C3 -2.3(3) . . . . ?
C9 N1 C2 C3 -178.90(17) . . . . ?
N1 C2 C3 C4 1.3(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C2 N1 C6 C5 1.4(3) . . . . ?
C2 N1 C6 N7 -176.85(16) . . . . ?
C9 N1 C6 C5 178.74(16) . . . . ?
C9 N1 C6 N7 0.46(19) . . . . ?
C4 C5 C6 N1 0.4(3) . . . . ?
C4 C5 C6 N7 178.2(2) . . . . ?
N1 C6 N7 C8 -0.7(2) . . . . ?
C5 C6 N7 C8 -178.70(19) . . . . ?
C6 N7 C8 C9 0.6(2) . . . . ?
N7 C8 C9 N1 -0.3(2) . . . . ?
N7 C8 C9 C10 179.93(17) . . . . ?
C2 N1 C9 C8 176.86(18) . . . . ?
C2 N1 C9 C10 -3.4(3) . . . . ?
C6 N1 C9 C8 -0.08(19) . . . . ?
C6 N1 C9 C10 179.69(16) . . . . ?
N1 C9 C10 C11 141.80(18) . . . . ?
N1 C9 C10 C15 -40.4(3) . . . . ?
C8 C9 C10 C11 -38.5(3) . . . . ?
C8 C9 C10 C15 139.3(2) . . . . ?
C9 C10 C11 C12 178.26(16) . . . . ?
C15 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C13 C14 C15 C10 2.4(3) . . . . ?
C9 C10 C15 C14 -179.68(17) . . . . ?
C11 C10 C15 C14 -1.9(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
N7 H7 Cl16 0.869(9) 2.223(10) 3.0800(15) 169.2(18) .
O17 H17A Cl16 0.854(10) 2.388(13) 3.1902(18) 157(2) .
O17 H17B O18 0.866(10) 1.924(10) 2.779(2) 169(2) 1_565
O18 H18A Cl16 0.841(10) 2.403(12) 3.1924(17) 157(2) .
O18 H18B O17 0.865(9) 1.936(10) 2.799(2) 175(2) 3_565

_diffrn_measured_fraction_theta_max 0.851
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.053

# Contents of RES file
_iucr_refine_instructions_details 
;
TITL mac67 in P2(1)/n
CELL 0.71073 11.2615 7.2071 16.8121 90.000 101.751 90.000
ZERR 4.00 0.0009 0.0006 0.0015 0.000 0.008 0.000
LATT 1
SYMM 0.5-X, 0.5+Y, 0.5-Z
SFAC C H N CL O
UNIT 52 60 8 4 8

REM colourless block
SIZE 0.30 0.20 0.20
TEMP -123
OMIT -1 2 1

L.S. 8
ACTA 52
BOND $H
CONF
FMAP 2
PLAN 10

DFIX N7 H7 0.88 0.01
DFIX O17 H17A O17 H17B O18 H18A O18 H18B 0.84 0.01
DFIX H17A H17B H18A H18B 1.28 0.02

EQIV $1 x, y+1, z
EQIV $2 -x, -y+1, -z
HTAB N7 CL16
HTAB O17 CL16
HTAB O17 O18_$1
HTAB O18 CL16
HTAB O18 O17_$2

rem DFIX 0.84 0.01 o1 h1a o1 h1b o2 h2a o2 h2b
rem DFIX 1.54 h1a h1b h2a h2b

REM EXTI 0.001436
WGHT 0.050700
FVAR 0.38653
N1 3 0.565037 0.268953 0.268329 11.00000 0.01919 0.02045 =
0.01739 0.00262 0.00474 0.00293
C2 1 0.568376 0.196691 0.344546 11.00000 0.02600 0.02525 =
0.01859 0.00209 0.00350 0.00292
AFIX 43
H2 2 0.643609 0.179905 0.381398 11.00000 -1.20000
AFIX 0
C3 1 0.463321 0.150034 0.366187 11.00000 0.03105 0.02924 =
0.02236 0.00261 0.01089 0.00200
AFIX 43
H3 2 0.464674 0.102457 0.419062 11.00000 -1.20000
AFIX 0
C4 1 0.351706 0.171073 0.311276 11.00000 0.02549 0.03104 =
0.03367 -0.00201 0.01507 0.00150
AFIX 43
H4 2 0.278508 0.138587 0.327648 11.00000 -1.20000
AFIX 0
C5 1 0.347607 0.237700 0.234727 11.00000 0.02020 0.02942 =
0.03087 0.00010 0.00338 0.00400
AFIX 43
H5 2 0.272826 0.249763 0.196935 11.00000 -1.20000
AFIX 0
C6 1 0.457040 0.287388 0.213999 11.00000 0.02175 0.02124 =
0.02045 0.00053 0.00283 0.00420
N7 3 0.482853 0.351640 0.144521 11.00000 0.02271 0.02612 =
0.02118 0.00473 0.00068 0.00362
H7 2 0.427833 0.390023 0.103896 11.00000 -1.20000
C8 1 0.605053 0.376271 0.154023 11.00000 0.02716 0.02194 =
0.02189 0.00131 0.00779 -0.00051
AFIX 43
H8 2 0.645482 0.421686 0.113592 11.00000 -1.20000
AFIX 0
C9 1 0.659520 0.325594 0.230347 11.00000 0.02096 0.01995 =
0.01991 0.00106 0.00780 0.00173
C10 1 0.788019 0.325590 0.270376 11.00000 0.02136 0.01597 =
0.02335 0.00159 0.00571 -0.00041
C11 1 0.873231 0.273265 0.224422 11.00000 0.02706 0.02143 =
0.02324 0.00261 0.00871 0.00017
AFIX 43
H11 2 0.846885 0.235880 0.169470 11.00000 -1.20000
AFIX 0
C12 1 0.995705 0.275960 0.258958 11.00000 0.02469 0.02761 =
0.03960 0.00300 0.01500 0.00105
AFIX 43
H12 2 1.053275 0.241781 0.227405 11.00000 -1.20000
AFIX 0
C13 1 1.034611 0.327952 0.338869 11.00000 0.02060 0.02837 =
0.04631 0.00124 0.00128 -0.00075
AFIX 43
H13 2 1.118787 0.328984 0.362412 11.00000 -1.20000
AFIX 0
C14 1 0.951057 0.378591 0.384730 11.00000 0.02840 0.03273 =
0.02728 -0.00464 -0.00227 -0.00145
AFIX 43
H14 2 0.978009 0.412056 0.440125 11.00000 -1.20000
AFIX 0
C15 1 0.828103 0.380939 0.350497 11.00000 0.02527 0.02479 =
0.02611 -0.00176 0.00580 0.00314
AFIX 43
H15 2 0.771389 0.420345 0.381802 11.00000 -1.20000
AFIX 0
CL16 4 0.263285 0.481857 0.016013 11.00000 0.02372 0.03403 =
0.01968 0.00030 0.00116 0.00173
O17 5 0.140424 0.876942 -0.029556 11.00000 0.05482 0.04254 =
0.04326 0.00100 0.01684 0.00417
H17A 2 0.184867 0.789739 -0.005278 11.00000 -1.50000
H17B 2 0.132720 0.953169 0.008883 11.00000 -1.50000
O18 5 0.111467 0.157884 0.078099 11.00000 0.04687 0.05287 =
0.04244 -0.00025 0.00541 -0.00639
H18A 2 0.131462 0.247730 0.051676 11.00000 -1.50000
H18B 2 0.033655 0.143005 0.065799 11.00000 -1.50000

HKLF 4

REM mac67 in P2(1)/n
REM R1 = 0.0393 for 2167 Fo > 4sig(Fo) and 0.0643 for all 3170 data
REM 178 parameters refined using 7 restraints

END

;
_database_code_depnum_ccdc_archive 'CCDC 907273'
#######################################################################
#
#                 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_mac93_7
#TrackingRef '14897_web_deposit_cif_file_0_BillClegg_1351029791.combined.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H9 I O2'
_chemical_formula_sum            'C15 H9 I O2'
_chemical_formula_weight         348.12

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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/c'

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

_cell_length_a                   9.2369(3)
_cell_length_b                   9.8428(2)
_cell_length_c                   14.2265(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.321(3)
_cell_angle_gamma                90.00
_cell_volume                     1258.63(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5062
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      28.41

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    2.534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.431
_exptl_absorpt_correction_T_max  0.570
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube with Enhance optics'
_diffrn_radiation_monochromator  none
_diffrn_measurement_device_type  
'Oxford Diffraction Gemini A Ultra diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.3968
_diffrn_reflns_number            6097
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         28.47
_reflns_number_total             2619
_reflns_number_gt                2392
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'

_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^)+(0.0192P)^2^+0.8029P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2619
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0194
_refine_ls_R_factor_gt           0.0166
_refine_ls_wR_factor_ref         0.0403
_refine_ls_wR_factor_gt          0.0396
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.004
_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
I I 0.829481(14) 0.548094(12) 0.617274(9) 0.02051(6) Uani 1 1 d . . .
O1 O 0.99273(16) 0.39632(15) 0.70951(10) 0.0256(3) Uani 1 1 d . . .
O2 O 1.10426(16) 0.19734(15) 0.69929(10) 0.0280(3) Uani 1 1 d . . .
C1 C 1.0214(2) 0.2910(2) 0.66383(14) 0.0204(4) Uani 1 1 d . . .
C2 C 0.9444(2) 0.28878(19) 0.55869(14) 0.0182(4) Uani 1 1 d . . .
C3 C 0.9656(2) 0.1830(2) 0.49862(15) 0.0233(4) Uani 1 1 d . . .
H3 H 1.0329 0.1117 0.5235 0.028 Uiso 1 1 calc R . .
C4 C 0.8896(3) 0.1806(2) 0.40300(16) 0.0280(5) Uani 1 1 d . . .
H4 H 0.9034 0.1073 0.3625 0.034 Uiso 1 1 calc R . .
C5 C 0.7930(3) 0.2855(2) 0.36609(15) 0.0294(5) Uani 1 1 d . . .
H5 H 0.7411 0.2834 0.3002 0.035 Uiso 1 1 calc R . .
C6 C 0.7710(2) 0.3932(2) 0.42371(15) 0.0245(4) Uani 1 1 d . . .
H6 H 0.7054 0.4655 0.3985 0.029 Uiso 1 1 calc R . .
C7 C 0.8479(2) 0.39165(19) 0.51913(13) 0.0180(4) Uani 1 1 d . . .
C8 C 0.6843(2) 0.6564(2) 0.51300(16) 0.0287(5) Uani 1 1 d . . .
C9 C 0.6106(2) 0.7421(2) 0.46513(15) 0.0259(5) Uani 1 1 d . . .
C10 C 0.5237(2) 0.8471(2) 0.40782(15) 0.0230(4) Uani 1 1 d . . .
C11 C 0.5814(2) 0.9177(2) 0.33999(16) 0.0295(5) Uani 1 1 d . . .
H11 H 0.6757 0.8936 0.3289 0.035 Uiso 1 1 calc R . .
C12 C 0.5006(3) 1.0230(2) 0.28881(17) 0.0314(5) Uani 1 1 d . . .
H12 H 0.5400 1.0718 0.2427 0.038 Uiso 1 1 calc R . .
C13 C 0.3629(3) 1.0579(2) 0.30422(17) 0.0302(5) Uani 1 1 d . . .
H13 H 0.3085 1.1311 0.2694 0.036 Uiso 1 1 calc R . .
C14 C 0.3044(2) 0.9861(2) 0.37046(17) 0.0298(5) Uani 1 1 d . . .
H14 H 0.2088 1.0088 0.3799 0.036 Uiso 1 1 calc R . .
C15 C 0.3843(2) 0.8819(2) 0.42287(16) 0.0267(5) Uani 1 1 d . . .
H15 H 0.3445 0.8339 0.4691 0.032 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I 0.02469(9) 0.01689(8) 0.01958(8) -0.00211(5) 0.00433(5) 0.00173(5)
O1 0.0298(8) 0.0283(8) 0.0165(7) -0.0012(6) 0.0010(6) 0.0025(6)
O2 0.0264(8) 0.0296(8) 0.0266(8) 0.0106(7) 0.0033(6) 0.0056(7)
C1 0.0179(10) 0.0235(10) 0.0198(9) 0.0057(9) 0.0042(7) -0.0034(8)
C2 0.0183(10) 0.0160(9) 0.0202(9) 0.0026(8) 0.0046(7) -0.0022(7)
C3 0.0260(11) 0.0169(9) 0.0288(11) 0.0003(9) 0.0101(9) 0.0013(8)
C4 0.0376(13) 0.0208(10) 0.0276(11) -0.0062(9) 0.0118(9) -0.0040(9)
C5 0.0394(13) 0.0284(11) 0.0181(10) -0.0027(9) 0.0020(9) -0.0041(10)
C6 0.0287(11) 0.0217(10) 0.0209(10) 0.0028(9) 0.0009(8) 0.0008(9)
C7 0.0235(10) 0.0126(9) 0.0181(9) -0.0020(8) 0.0049(8) -0.0016(7)
C8 0.0312(12) 0.0213(10) 0.0326(11) 0.0002(10) 0.0056(9) 0.0052(9)
C9 0.0277(11) 0.0198(10) 0.0295(11) -0.0046(10) 0.0052(9) 0.0004(9)
C10 0.0226(10) 0.0168(9) 0.0261(10) -0.0030(9) -0.0014(8) 0.0013(8)
C11 0.0227(11) 0.0334(12) 0.0315(11) -0.0007(10) 0.0046(9) 0.0034(9)
C12 0.0317(12) 0.0309(12) 0.0300(11) 0.0050(10) 0.0039(9) -0.0019(10)
C13 0.0293(12) 0.0231(11) 0.0315(11) -0.0010(10) -0.0066(9) 0.0051(9)
C14 0.0202(11) 0.0309(11) 0.0354(12) -0.0050(10) 0.0007(9) 0.0043(9)
C15 0.0239(11) 0.0241(11) 0.0308(11) -0.0007(10) 0.0037(9) -0.0008(8)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I O1 2.3056(14) . ?
I O2 2.9337(14) 2_756 ?
I C7 2.1117(18) . ?
I C8 2.054(2) . ?
O1 C1 1.283(2) . ?
O2 I 2.9337(14) 2_746 ?
O2 C1 1.230(2) . ?
C1 C2 1.501(3) . ?
C2 C3 1.390(3) . ?
C2 C7 1.380(3) . ?
C3 H3 0.950 . ?
C3 C4 1.380(3) . ?
C4 H4 0.950 . ?
C4 C5 1.386(3) . ?
C5 H5 0.950 . ?
C5 C6 1.383(3) . ?
C6 H6 0.950 . ?
C6 C7 1.380(3) . ?
C8 C9 1.194(3) . ?
C9 C10 1.441(3) . ?
C10 C11 1.391(3) . ?
C10 C15 1.396(3) . ?
C11 H11 0.950 . ?
C11 C12 1.383(3) . ?
C12 H12 0.950 . ?
C12 C13 1.383(3) . ?
C13 H13 0.950 . ?
C13 C14 1.383(3) . ?
C14 H14 0.950 . ?
C14 C15 1.378(3) . ?
C15 H15 0.950 . ?

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
O1 I O2 80.98(5) . 2_756 ?
O1 I C7 76.23(6) . . ?
O1 I C8 168.50(7) . . ?
O2 I C7 157.10(6) 2_756 . ?
O2 I C8 110.51(7) 2_756 . ?
C7 I C8 92.27(8) . . ?
I O1 C1 114.80(12) . . ?
I O2 C1 136.29(13) 2_746 . ?
O1 C1 O2 125.41(18) . . ?
O1 C1 C2 114.26(17) . . ?
O2 C1 C2 120.33(18) . . ?
C1 C2 C3 121.48(18) . . ?
C1 C2 C7 120.58(17) . . ?
C3 C2 C7 117.93(18) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.45(19) . . ?
H3 C3 C4 119.8 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.9(2) . . ?
H4 C4 C5 120.1 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(2) . . ?
H5 C5 C6 119.5 . . ?
C5 C6 H6 121.2 . . ?
C5 C6 C7 117.5(2) . . ?
H6 C6 C7 121.2 . . ?
I C7 C2 114.09(13) . . ?
I C7 C6 122.74(15) . . ?
C2 C7 C6 123.16(18) . . ?
I C8 C9 165.99(19) . . ?
C8 C9 C10 179.1(2) . . ?
C9 C10 C11 119.87(19) . . ?
C9 C10 C15 120.2(2) . . ?
C11 C10 C15 119.90(19) . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(2) . . ?
H11 C11 C12 120.2 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.5(2) . . ?
H12 C12 C13 119.8 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 119.9(2) . . ?
H13 C13 C14 120.0 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.3(2) . . ?
H14 C14 C15 119.8 . . ?
C10 C15 C14 119.8(2) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?

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
O2 I O1 C1 -177.64(14) 2_756 . . . ?
C7 I O1 C1 0.17(14) . . . . ?
C8 I O1 C1 -1.0(4) . . . . ?
I O2 C1 O1 38.7(3) 2_746 . . . ?
I O2 C1 C2 -141.67(15) 2_746 . . . ?
I O1 C1 O2 -179.40(16) . . . . ?
I O1 C1 C2 0.9(2) . . . . ?
O1 C1 C2 C3 178.88(18) . . . . ?
O1 C1 C2 C7 -2.2(3) . . . . ?
O2 C1 C2 C3 -0.8(3) . . . . ?
O2 C1 C2 C7 178.10(18) . . . . ?
C1 C2 C3 C4 177.67(19) . . . . ?
C7 C2 C3 C4 -1.3(3) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C5 C6 C7 I 179.51(16) . . . . ?
C5 C6 C7 C2 0.1(3) . . . . ?
C1 C2 C7 I 2.3(2) . . . . ?
C1 C2 C7 C6 -178.20(19) . . . . ?
C3 C2 C7 I -178.70(14) . . . . ?
C3 C2 C7 C6 0.8(3) . . . . ?
O1 I C7 C2 -1.29(13) . . . . ?
O1 I C7 C6 179.24(18) . . . . ?
O2 I C7 C2 4.3(3) 2_756 . . . ?
O2 I C7 C6 -175.19(13) 2_756 . . . ?
C8 I C7 C2 178.47(15) . . . . ?
C8 I C7 C6 -0.99(18) . . . . ?
O1 I C8 C9 -155.5(7) . . . . ?
O2 I C8 C9 21.0(9) 2_756 . . . ?
C7 I C8 C9 -156.6(8) . . . . ?
C9 C10 C11 C12 -176.7(2) . . . . ?
C15 C10 C11 C12 0.8(3) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 C15 1.5(3) . . . . ?
C13 C14 C15 C10 -1.1(3) . . . . ?
C9 C10 C15 C14 177.4(2) . . . . ?
C11 C10 C15 C14 0.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.822
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.065

# Contents of RES file
_iucr_refine_instructions_details 
;
TITL mac93 in P2(1)/c
CELL 0.71073 9.2369 9.8428 14.2265 90.000 103.321 90.000
ZERR 4.00 0.0003 0.0002 0.0004 0.000 0.003 0.000
LATT 1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C H O I
UNIT 60 36 8 4

SIZE 0.4 0.4 0.25
TEMP -123

L.S. 8
ACTA 52
BOND $H
CONF
FMAP 2
PLAN 10

EQIV $1 2-X, 0.5+Y, 1.5-Z
EQIV $2 2-X, -0.5+Y, 1.5-Z
BIND I O2_$1
BIND O2 I_$2

WGHT 0.019200 0.802900
EXTI 0.001328
FVAR 0.14079
I 4 0.829481 0.548094 0.617274 11.00000 0.02469 0.01689 =
0.01958 -0.00211 0.00433 0.00173
O1 3 0.992734 0.396315 0.709506 11.00000 0.02977 0.02834 =
0.01650 -0.00115 0.00098 0.00247
O2 3 1.104263 0.197341 0.699291 11.00000 0.02637 0.02962 =
0.02663 0.01061 0.00329 0.00563
C1 1 1.021400 0.291004 0.663825 11.00000 0.01792 0.02348 =
0.01981 0.00571 0.00419 -0.00343
C2 1 0.944417 0.288778 0.558691 11.00000 0.01833 0.01599 =
0.02021 0.00260 0.00455 -0.00222
C3 1 0.965624 0.182951 0.498619 11.00000 0.02595 0.01695 =
0.02884 0.00029 0.01007 0.00132
AFIX 43
H3 2 1.032946 0.111713 0.523547 11.00000 -1.20000
AFIX 0
C4 1 0.889563 0.180631 0.403003 11.00000 0.03757 0.02081 =
0.02758 -0.00621 0.01176 -0.00402
AFIX 43
H4 2 0.903368 0.107285 0.362548 11.00000 -1.20000
AFIX 0
C5 1 0.792988 0.285499 0.366089 11.00000 0.03942 0.02838 =
0.01806 -0.00273 0.00197 -0.00408
AFIX 43
H5 2 0.741066 0.283378 0.300176 11.00000 -1.20000
AFIX 0
C6 1 0.771013 0.393198 0.423707 11.00000 0.02870 0.02169 =
0.02086 0.00278 0.00090 0.00082
AFIX 43
H6 2 0.705409 0.465531 0.398508 11.00000 -1.20000
AFIX 0
C7 1 0.847920 0.391650 0.519131 11.00000 0.02349 0.01259 =
0.01814 -0.00203 0.00494 -0.00164
C8 1 0.684255 0.656371 0.512997 11.00000 0.03120 0.02133 =
0.03262 0.00019 0.00559 0.00523
C9 1 0.610615 0.742093 0.465126 11.00000 0.02770 0.01977 =
0.02951 -0.00463 0.00523 0.00036
C10 1 0.523683 0.847149 0.407815 11.00000 0.02262 0.01681 =
0.02609 -0.00301 -0.00136 0.00132
C11 1 0.581380 0.917686 0.339990 11.00000 0.02266 0.03340 =
0.03153 -0.00065 0.00458 0.00342
AFIX 43
H11 2 0.675652 0.893635 0.328899 11.00000 -1.20000
AFIX 0
C12 1 0.500637 1.023050 0.288805 11.00000 0.03173 0.03088 =
0.02996 0.00504 0.00390 -0.00186
AFIX 43
H12 2 0.540033 1.071824 0.242729 11.00000 -1.20000
AFIX 0
C13 1 0.362912 1.057929 0.304221 11.00000 0.02929 0.02311 =
0.03146 -0.00096 -0.00657 0.00513
AFIX 43
H13 2 0.308523 1.131113 0.269354 11.00000 -1.20000
AFIX 0
C14 1 0.304443 0.986144 0.370457 11.00000 0.02018 0.03087 =
0.03545 -0.00496 0.00069 0.00427
AFIX 43
H14 2 0.208799 1.008798 0.379852 11.00000 -1.20000
AFIX 0
C15 1 0.384266 0.881946 0.422867 11.00000 0.02393 0.02409 =
0.03078 -0.00075 0.00367 -0.00084
AFIX 43
H15 2 0.344538 0.833911 0.469122 11.00000 -1.20000

HKLF 4

REM mac93 in P2(1)/c
REM R1 = 0.0166 for 2392 Fo > 4sig(Fo) and 0.0194 for all 2619 data
REM 164 parameters refined using 0 restraints

END

;

#===END


_database_code_depnum_ccdc_archive 'CCDC 907274'