# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
_chemical_name_systematic        ?
_chemical_name_common            rgz1456
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H26 Cl N2 O Rh'
_chemical_formula_iupac          ?
_chemical_formula_weight         484.82

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.66000(10)
_cell_length_b                   10.1287(2)
_cell_length_c                   15.0794(3)
_cell_angle_alpha                80.4470(10)
_cell_angle_beta                 75.5470(10)
_cell_angle_gamma                72.9940(10)
_cell_volume                     1077.91(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9932
_cell_measurement_theta_min      2.6510
_cell_measurement_theta_max      28.1101
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496

_exptl_absorpt_coefficient_mu    0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.86

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            39981
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0123
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             3940
_reflns_number_gt                3707
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0201
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0707
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_number_reflns         3940
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0481P)²+0.5725P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.309
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3025(4) 0.1434(3) 0.48170(18) 0.0517(6) Uani d . 1 . .
H H1 0.2901 0.0587 0.4716 0.062 Uiso calc R 1 . .
C C2 0.3166(4) 0.1604(3) 0.56814(19) 0.0615(7) Uani d . 1 . .
H H2 0.3141 0.0885 0.6153 0.074 Uiso calc R 1 . .
C C3 0.3342(4) 0.2851(3) 0.58348(19) 0.0637(8) Uani d . 1 . .
H H3 0.3429 0.2997 0.6413 0.076 Uiso calc R 1 . .
C C4 0.3386(4) 0.3881(3) 0.5117(2) 0.0575(7) Uani d . 1 . .
H H4 0.3499 0.4736 0.5207 0.069 Uiso calc R 1 . .
C C5 0.3264(3) 0.3643(2) 0.42622(17) 0.0423(5) Uani d . 1 . .
C C6 0.3517(4) 0.4668(2) 0.34274(18) 0.0471(6) Uani d . 1 . .
C C7 0.3914(3) 0.5053(3) 0.18160(18) 0.0475(6) Uani d . 1 . .
H H7A 0.4427 0.4423 0.134 0.057 Uiso calc R 1 . .
H H7B 0.4918 0.5409 0.188 0.057 Uiso calc R 1 . .
C C8 0.2423(3) 0.6258(2) 0.14935(16) 0.0411(5) Uani d . 1 . .
C C9 0.0964(4) 0.7018(3) 0.21089(18) 0.0478(6) Uani d . 1 . .
H H9 0.0848 0.6767 0.2738 0.057 Uiso calc R 1 . .
C C10 -0.0323(4) 0.8157(3) 0.1785(2) 0.0575(7) Uani d . 1 . .
H H10 -0.1305 0.866 0.2201 0.069 Uiso calc R 1 . .
C C11 -0.0166(4) 0.8546(3) 0.0863(2) 0.0623(7) Uani d . 1 . .
H H11 -0.103 0.9314 0.0654 0.075 Uiso calc R 1 . .
C C12 0.1272(5) 0.7799(3) 0.0246(2) 0.0637(8) Uani d . 1 . .
H H12 0.1382 0.8056 -0.0383 0.076 Uiso calc R 1 . .
C C13 0.2556(4) 0.6662(3) 0.05633(18) 0.0526(6) Uani d . 1 . .
H H13 0.3528 0.616 0.0143 0.063 Uiso calc R 1 . .
C C14 0.0164(3) 0.1947(3) 0.30334(19) 0.0506(6) Uani d . 1 . .
C C15 0.0385(4) 0.2853(3) 0.2211(2) 0.0576(7) Uani d . 1 . .
C C16 0.1944(4) 0.2152(4) 0.15664(19) 0.0635(8) Uani d . 1 . .
C C17 0.2583(4) 0.0778(4) 0.1984(2) 0.0629(8) Uani d . 1 . .
C C18 0.1527(4) 0.0650(3) 0.2885(2) 0.0531(6) Uani d . 1 . .
C C19 -0.1320(5) 0.2283(5) 0.3878(2) 0.0826(11) Uani d . 1 . .
H H19A -0.187 0.3267 0.385 0.124 Uiso calc R 1 . .
H H19B -0.0779 0.1983 0.4412 0.124 Uiso calc R 1 . .
H H19C -0.2264 0.1816 0.3917 0.124 Uiso calc R 1 . .
C C20 -0.0871(5) 0.4257(4) 0.2034(4) 0.1023(15) Uani d . 1 . .
H H20A -0.022 0.478 0.154 0.153 Uiso calc R 1 . .
H H20B -0.1243 0.473 0.258 0.153 Uiso calc R 1 . .
H H20C -0.1959 0.4166 0.1868 0.153 Uiso calc R 1 . .
C C21 0.2660(7) 0.2699(6) 0.0590(2) 0.121(2) Uani d . 1 . .
H H21A 0.2223 0.2314 0.0173 0.181 Uiso calc R 1 . .
H H21B 0.4001 0.2439 0.0454 0.181 Uiso calc R 1 . .
H H21C 0.2211 0.3692 0.0521 0.181 Uiso calc R 1 . .
C C22 0.4122(5) -0.0378(5) 0.1539(3) 0.1112(18) Uani d . 1 . .
H H22A 0.4722 -0.098 0.2001 0.167 Uiso calc R 1 . .
H H22B 0.5021 0.0006 0.109 0.167 Uiso calc R 1 . .
H H22C 0.3603 -0.0898 0.1245 0.167 Uiso calc R 1 . .
C C23 0.1659(7) -0.0648(4) 0.3543(3) 0.0935(13) Uani d . 1 . .
H H23A 0.075 -0.1101 0.3496 0.14 Uiso calc R 1 . .
H H23B 0.1423 -0.0412 0.416 0.14 Uiso calc R 1 . .
H H23C 0.2888 -0.1262 0.3392 0.14 Uiso calc R 1 . .
Cl Cl1 0.62496(8) 0.14596(6) 0.23925(5) 0.04952(15) Uani d . 1 . .
N N1 0.3060(3) 0.2433(2) 0.41151(13) 0.0401(4) Uani d . 1 . .
N N2 0.3306(3) 0.42658(19) 0.26795(14) 0.0397(4) Uani d . 1 . .
O O1 0.3947(4) 0.5730(2) 0.34926(16) 0.0722(6) Uani d . 1 . .
Rh Rh1 0.28969(2) 0.229797(16) 0.275822(11) 0.03537(8) Uani d . 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.339(3) ?
C1 C2 . 1.377(4) ?
C1 H1 . 0.93 ?
C2 C3 . 1.371(4) ?
C2 H2 . 0.93 ?
C3 C4 . 1.375(4) ?
C3 H3 . 0.93 ?
C4 C5 . 1.380(4) ?
C4 H4 . 0.93 ?
C5 N1 . 1.340(3) ?
C5 C6 . 1.504(4) ?
C6 O1 . 1.239(3) ?
C6 N2 . 1.321(3) ?
C7 N2 . 1.455(3) ?
C7 C8 . 1.515(3) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C8 C13 . 1.381(4) ?
C8 C9 . 1.385(3) ?
C9 C10 . 1.389(4) ?
C9 H9 . 0.93 ?
C10 C11 . 1.365(4) ?
C10 H10 . 0.93 ?
C11 C12 . 1.374(4) ?
C11 H11 . 0.93 ?
C12 C13 . 1.383(4) ?
C12 H12 . 0.93 ?
C13 H13 . 0.93 ?
C14 C15 . 1.420(4) ?
C14 C18 . 1.430(4) ?
C14 C19 . 1.492(4) ?
C14 Rh1 . 2.152(2) ?
C15 C16 . 1.424(4) ?
C15 C20 . 1.491(4) ?
C15 Rh1 . 2.169(2) ?
C16 C17 . 1.427(5) ?
C16 C21 . 1.510(5) ?
C16 Rh1 . 2.143(3) ?
C17 C18 . 1.404(4) ?
C17 C22 . 1.506(4) ?
C17 Rh1 . 2.178(2) ?
C18 C23 . 1.504(5) ?
C18 Rh1 . 2.178(2) ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
C20 H20A . 0.96 ?
C20 H20B . 0.96 ?
C20 H20C . 0.96 ?
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?
C22 H22A . 0.96 ?
C22 H22B . 0.96 ?
C22 H22C . 0.96 ?
C23 H23A . 0.96 ?
C23 H23B . 0.96 ?
C23 H23C . 0.96 ?
Cl1 Rh1 . 2.4070(6) ?
N1 Rh1 . 2.1099(19) ?
N2 Rh1 . 2.0865(19) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 122.9(3) ?
N1 C1 H1 . . 118.6 ?
C2 C1 H1 . . 118.6 ?
C1 C2 C3 . . 118.8(3) ?
C1 C2 H2 . . 120.6 ?
C3 C2 H2 . . 120.6 ?
C4 C3 C2 . . 118.7(3) ?
C4 C3 H3 . . 120.7 ?
C2 C3 H3 . . 120.7 ?
C3 C4 C5 . . 119.8(3) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
N1 C5 C4 . . 121.5(2) ?
N1 C5 C6 . . 116.0(2) ?
C4 C5 C6 . . 122.3(2) ?
O1 C6 N2 . . 127.5(3) ?
O1 C6 C5 . . 119.3(2) ?
N2 C6 C5 . . 113.1(2) ?
N2 C7 C8 . . 115.8(2) ?
N2 C7 H7A . . 108.3 ?
C8 C7 H7A . . 108.3 ?
N2 C7 H7B . . 108.3 ?
C8 C7 H7B . . 108.3 ?
H7A C7 H7B . . 107.4 ?
C13 C8 C9 . . 118.5(2) ?
C13 C8 C7 . . 119.6(2) ?
C9 C8 C7 . . 121.8(2) ?
C8 C9 C10 . . 119.9(2) ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
C11 C10 C9 . . 120.8(3) ?
C11 C10 H10 . . 119.6 ?
C9 C10 H10 . . 119.6 ?
C10 C11 C12 . . 119.8(3) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
C11 C12 C13 . . 119.7(3) ?
C11 C12 H12 . . 120.2 ?
C13 C12 H12 . . 120.2 ?
C8 C13 C12 . . 121.3(2) ?
C8 C13 H13 . . 119.4 ?
C12 C13 H13 . . 119.4 ?
C15 C14 C18 . . 108.2(2) ?
C15 C14 C19 . . 125.1(3) ?
C18 C14 C19 . . 126.6(3) ?
C15 C14 Rh1 . . 71.46(14) ?
C18 C14 Rh1 . . 71.70(14) ?
C19 C14 Rh1 . . 125.41(19) ?
C16 C15 C14 . . 108.1(3) ?
C16 C15 C20 . . 125.9(3) ?
C14 C15 C20 . . 125.8(3) ?
C16 C15 Rh1 . . 69.70(15) ?
C14 C15 Rh1 . . 70.18(14) ?
C20 C15 Rh1 . . 128.6(2) ?
C15 C16 C17 . . 106.9(2) ?
C15 C16 C21 . . 126.7(4) ?
C17 C16 C21 . . 126.1(4) ?
C15 C16 Rh1 . . 71.73(15) ?
C17 C16 Rh1 . . 72.05(16) ?
C21 C16 Rh1 . . 126.3(2) ?
C18 C17 C16 . . 109.3(3) ?
C18 C17 C22 . . 124.4(4) ?
C16 C17 C22 . . 126.3(3) ?
C18 C17 Rh1 . . 71.20(14) ?
C16 C17 Rh1 . . 69.37(15) ?
C22 C17 Rh1 . . 126.5(2) ?
C17 C18 C14 . . 107.4(3) ?
C17 C18 C23 . . 126.6(3) ?
C14 C18 C23 . . 125.7(3) ?
C17 C18 Rh1 . . 71.18(15) ?
C14 C18 Rh1 . . 69.75(14) ?
C23 C18 Rh1 . . 129.0(2) ?
C14 C19 H19A . . 109.5 ?
C14 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C14 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C15 C20 H20A . . 109.5 ?
C15 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C15 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C16 C21 H21A . . 109.5 ?
C16 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C16 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C17 C22 H22A . . 109.5 ?
C17 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C17 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C18 C23 H23A . . 109.5 ?
C18 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C18 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C5 N1 C1 . . 118.2(2) ?
C5 N1 Rh1 . . 115.12(16) ?
C1 N1 Rh1 . . 126.62(17) ?
C6 N2 C7 . . 115.8(2) ?
C6 N2 Rh1 . . 118.33(16) ?
C7 N2 Rh1 . . 123.42(16) ?
N2 Rh1 N1 . . 77.06(8) ?
N2 Rh1 C16 . . 109.05(11) ?
N1 Rh1 C16 . . 163.90(10) ?
N2 Rh1 C14 . . 122.73(9) ?
N1 Rh1 C14 . . 99.19(9) ?
C16 Rh1 C14 . . 64.84(10) ?
N2 Rh1 C15 . . 99.50(9) ?
N1 Rh1 C15 . . 126.84(10) ?
C16 Rh1 C15 . . 38.57(12) ?
C14 Rh1 C15 . . 38.36(11) ?
N2 Rh1 C17 . . 145.08(12) ?
N1 Rh1 C17 . . 137.81(11) ?
C16 Rh1 C17 . . 38.58(13) ?
C14 Rh1 C17 . . 63.64(10) ?
C15 Rh1 C17 . . 63.61(11) ?
N2 Rh1 C18 . . 161.19(10) ?
N1 Rh1 C18 . . 104.68(9) ?
C16 Rh1 C18 . . 64.62(11) ?
C14 Rh1 C18 . . 38.55(10) ?
C15 Rh1 C18 . . 64.12(11) ?
C17 Rh1 C18 . . 37.62(11) ?
N2 Rh1 Cl1 . . 86.44(5) ?
N1 Rh1 Cl1 . . 88.41(5) ?
C16 Rh1 Cl1 . . 106.59(9) ?
C14 Rh1 Cl1 . . 150.78(8) ?
C15 Rh1 Cl1 . . 144.74(9) ?
C17 Rh1 Cl1 . . 91.88(7) ?
C18 Rh1 Cl1 . . 112.24(8) ?

_database_code_depnum_ccdc_archive 'CCDC 994046'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_I
_chemical_name_systematic        ?
_chemical_name_common            rzg1561
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         294.30

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   7.5891(13)
_cell_length_b                   11.2221(16)
_cell_length_c                   17.124(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.544(6)
_cell_angle_gamma                90
_cell_volume                     1458.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2836
_cell_measurement_theta_min      2.9263
_cell_measurement_theta_max      24.0768
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616

_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            10397
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             2659
_reflns_number_gt                1864
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1442
_refine_ls_R_factor_gt           0.1108
_refine_ls_wR_factor_gt          0.3595
_refine_ls_wR_factor_ref         0.3853
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.148
_refine_ls_number_reflns         2659
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1773P)²+4.1421P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.376
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       0.020(7)

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'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7465(8) 0.0804(5) 0.0276(3) 0.0458(14) Uani d . 1 . .
C C2 0.7821(10) 0.0558(6) -0.0494(4) 0.0581(17) Uani d . 1 . .
H H2 0.7821 -0.0217 -0.0686 0.07 Uiso calc R 1 . .
C C3 0.8170(12) 0.1500(7) -0.0954(4) 0.074(2) Uani d . 1 . .
H H3 0.8429 0.1372 -0.1477 0.089 Uiso calc R 1 . .
C C4 0.8154(11) 0.2657(7) -0.0669(5) 0.073(2) Uani d . 1 . .
H H4 0.8358 0.3278 -0.1017 0.088 Uiso calc R 1 . .
C C6 0.7518(8) 0.1991(5) 0.0524(4) 0.0503(15) Uani d . 1 . .
C C7 0.7124(8) 0.2050(5) 0.1366(4) 0.0525(16) Uani d . 1 . .
C C8 0.7025(8) 0.0082(5) 0.0980(3) 0.0433(13) Uani d . 1 . .
C C9 0.6496(8) 0.0586(6) 0.2407(3) 0.0522(16) Uani d . 1 . .
H H9A 0.6928 0.1222 0.2742 0.063 Uiso calc R 1 . .
H H9B 0.7139 -0.0133 0.2542 0.063 Uiso calc R 1 . .
C C10 0.4559(8) 0.0392(5) 0.2563(3) 0.0451(14) Uani d . 1 . .
C C11 0.3278(9) 0.1107(7) 0.2272(4) 0.0629(18) Uani d . 1 . .
H H11 0.3575 0.1726 0.1937 0.075 Uiso calc R 1 . .
C C12 0.1537(10) 0.0930(9) 0.2464(5) 0.083(2) Uani d . 1 . .
H H12 0.0669 0.1411 0.2243 0.1 Uiso calc R 1 . .
C C13 0.1086(11) 0.0066(9) 0.2968(5) 0.081(2) Uani d . 1 . .
H H13 -0.0084 -0.003 0.3111 0.097 Uiso calc R 1 . .
C C14 0.2363(10) -0.0671(6) 0.3270(4) 0.0620(18) Uani d . 1 . .
H H14 0.2055 -0.1279 0.3612 0.074 Uiso calc R 1 . .
C C15 0.4082(9) -0.0515(6) 0.3069(4) 0.0559(17) Uani d . 1 . .
H H15 0.4941 -0.102 0.3274 0.067 Uiso calc R 1 . .
C C16 0.6848(9) -0.1084(5) 0.1110(3) 0.0517(16) Uani d . 1 . .
H H16 0.6589 -0.1309 0.1619 0.062 Uiso calc R 1 . .
C C17 0.7018(9) -0.2061(5) 0.0535(4) 0.0502(15) Uani d . 1 . .
C C18 0.7291(15) -0.4146(6) 0.0413(4) 0.084(3) Uani d . 1 . .
H H18A 0.6237 -0.4236 0.0105 0.127 Uiso calc R 1 . .
H H18B 0.7448 -0.4836 0.0739 0.127 Uiso calc R 1 . .
H H18C 0.8285 -0.4064 0.0075 0.127 Uiso calc R 1 . .
N N1 0.7863(8) 0.2924(5) 0.0067(4) 0.0663(16) Uani d . 1 . .
N N2 0.6853(6) 0.0895(4) 0.1588(3) 0.0471(12) Uani d . 1 . .
O O1 0.7073(7) 0.2917(4) 0.1789(3) 0.0731(16) Uani d . 1 . .
O O2 0.7038(10) -0.1970(4) -0.0170(3) 0.0833(19) Uani d . 1 . .
O O3 0.7144(8) -0.3098(4) 0.0897(3) 0.0669(15) Uani d . 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.375(9) ?
C1 C6 . 1.398(8) ?
C1 C8 . 1.494(8) ?
C2 C3 . 1.347(10) ?
C3 C4 . 1.387(11) ?
C4 N1 . 1.317(10) ?
C6 N1 . 1.334(8) ?
C6 C7 . 1.477(9) ?
C7 O1 . 1.214(7) ?
C7 N2 . 1.367(8) ?
C8 C16 . 1.334(9) ?
C8 N2 . 1.391(7) ?
C9 N2 . 1.472(8) ?
C9 C10 . 1.513(9) ?
C10 C11 . 1.352(9) ?
C10 C15 . 1.387(8) ?
C11 C12 . 1.379(11) ?
C12 C13 . 1.344(12) ?
C13 C14 . 1.372(12) ?
C14 C15 . 1.363(10) ?
C16 C17 . 1.480(8) ?
C17 O2 . 1.211(7) ?
C17 O3 . 1.323(7) ?
C18 O3 . 1.444(8) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 118.5(6) ?
C2 C1 C8 . . 135.4(6) ?
C6 C1 C8 . . 106.1(5) ?
C3 C2 C1 . . 116.4(6) ?
C2 C3 C4 . . 121.8(7) ?
N1 C4 C3 . . 123.4(7) ?
N1 C6 C1 . . 125.1(6) ?
N1 C6 C7 . . 125.4(6) ?
C1 C6 C7 . . 109.5(5) ?
O1 C7 N2 . . 126.0(6) ?
O1 C7 C6 . . 128.8(6) ?
N2 C7 C6 . . 105.2(5) ?
C16 C8 N2 . . 120.6(5) ?
C16 C8 C1 . . 133.6(5) ?
N2 C8 C1 . . 105.8(5) ?
N2 C9 C10 . . 113.0(5) ?
C11 C10 C15 . . 118.4(6) ?
C11 C10 C9 . . 123.1(6) ?
C15 C10 C9 . . 118.5(6) ?
C10 C11 C12 . . 120.9(7) ?
C13 C12 C11 . . 120.5(8) ?
C12 C13 C14 . . 119.6(7) ?
C15 C14 C13 . . 120.1(7) ?
C14 C15 C10 . . 120.5(7) ?
C8 C16 C17 . . 127.3(6) ?
O2 C17 O3 . . 122.7(5) ?
O2 C17 C16 . . 127.1(5) ?
O3 C17 C16 . . 110.2(5) ?
C4 N1 C6 . . 114.8(6) ?
C7 N2 C8 . . 113.4(5) ?
C7 N2 C9 . . 121.2(5) ?
C8 N2 C9 . . 125.3(5) ?
C17 O3 C18 . . 116.9(5) ?

_database_code_depnum_ccdc_archive 'CCDC 993801'
