# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1432530'
_audit_update_record             
;
2015-10-21 deposited with the CCDC.
2016-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 dimethyl 2,3-dicyano-1',3'-dioxo-1',3'-dihydrospiro[cyclopropane-1,2'-indene]-2,3-dicarboxylate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C17 H10 N2 O6)'
_chemical_formula_sum            'C34 H20 N4 O12'
_chemical_formula_weight         676.55

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   16.9250(3)
_cell_length_b                   17.9908(5)
_cell_length_c                   10.9836(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.315(3)
_cell_angle_gamma                90
_cell_volume                     3209.77(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .18
_exptl_crystal_size_mid          .15
_exptl_crystal_size_min          .12
_exptl_absorpt_coefficient_mu    0.923
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;
_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'


_diffrn_reflns_number            13507
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_av_R_equivalents  0.0979
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.666
_diffrn_reflns_theta_max         71.046
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             6088
_reflns_number_gt                4191
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0887P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6088
_refine_ls_number_parameters     456
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1465
_refine_ls_wR_factor_gt          0.1386
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_restrained_S_all      0.911
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.35490(10) 0.43439(10) 0.72522(16) 0.0605(4) Uani 1 1 d . . . . .
O2A O 0.63509(10) 0.44079(9) 0.73042(16) 0.0594(4) Uani 1 1 d . . . . .
O3A O 0.33641(10) 0.30966(9) 0.52212(14) 0.0551(4) Uani 1 1 d . . . . .
O4A O 0.35571(9) 0.41348(8) 0.42077(13) 0.0506(4) Uani 1 1 d . . . . .
O5A O 0.62011(10) 0.26985(10) 0.66205(15) 0.0593(4) Uani 1 1 d . . . . .
O6A O 0.61715(9) 0.29711(10) 0.86019(14) 0.0583(4) Uani 1 1 d . . . . .
N1A N 0.56325(14) 0.39135(16) 0.43089(19) 0.0759(7) Uani 1 1 d . . . . .
N2A N 0.41217(12) 0.24223(11) 0.79952(18) 0.0535(5) Uani 1 1 d . . . . .
C2A C 0.42661(13) 0.45133(11) 0.74824(18) 0.0425(5) Uani 1 1 d . . . . .
C3A C 0.49119(12) 0.41152(10) 0.70251(17) 0.0378(4) Uani 1 1 d . . . . .
C4A C 0.57016(13) 0.45584(11) 0.74929(18) 0.0426(5) Uani 1 1 d . . . . .
C5A C 0.60386(17) 0.57333(13) 0.8879(2) 0.0589(6) Uani 1 1 d . . . . .
H5A H 0.6591 0.5740 0.8897 0.071 Uiso 1 1 calc . U . . .
C6A C 0.5709(2) 0.62688(14) 0.9488(2) 0.0680(8) Uani 1 1 d . . . . .
H6A H 0.6045 0.6649 0.9921 0.082 Uiso 1 1 calc . U . . .
C7A C 0.4893(2) 0.62534(13) 0.9469(2) 0.0670(8) Uani 1 1 d . . . . .
H7A H 0.4691 0.6625 0.9890 0.080 Uiso 1 1 calc . U . . .
C8A C 0.43573(17) 0.56973(13) 0.8839(2) 0.0563(6) Uani 1 1 d . . . . .
H8A H 0.3807 0.5688 0.8832 0.068 Uiso 1 1 calc . U . . .
C9A C 0.46899(14) 0.51576(11) 0.82210(17) 0.0436(5) Uani 1 1 d . . . . .
C10A C 0.55078(14) 0.51820(11) 0.82360(17) 0.0447(5) Uani 1 1 d . . . . .
C11A C 0.46890(12) 0.36856(11) 0.57648(16) 0.0378(4) Uani 1 1 d . . . . .
C12A C 0.50061(12) 0.32662(10) 0.69964(16) 0.0355(4) Uani 1 1 d . . . . .
C13A C 0.44606(12) 0.28099(11) 0.74907(18) 0.0394(4) Uani 1 1 d . . . . .
C14A C 0.58678(13) 0.29464(11) 0.73531(19) 0.0429(5) Uani 1 1 d . . . . .
C15A C 0.69829(18) 0.2671(3) 0.9113(3) 0.1015(13) Uani 1 1 d . . . . .
H15A H 0.7005 0.2179 0.8786 0.152 Uiso 1 1 calc R U . . .
H15B H 0.7112 0.2652 1.0021 0.152 Uiso 1 1 calc R U . . .
H15C H 0.7375 0.2983 0.8874 0.152 Uiso 1 1 calc R U . . .
C16A C 0.52293(14) 0.37957(13) 0.49627(19) 0.0485(5) Uani 1 1 d . . . . .
C17A C 0.37843(13) 0.35948(11) 0.50460(18) 0.0413(5) Uani 1 1 d . . . . .
C18A C 0.27237(15) 0.40895(16) 0.3378(2) 0.0627(6) Uani 1 1 d . . . . .
H18A H 0.2681 0.3675 0.2813 0.094 Uiso 1 1 calc R U . . .
H18B H 0.2592 0.4540 0.2894 0.094 Uiso 1 1 calc R U . . .
H18C H 0.2346 0.4024 0.3879 0.094 Uiso 1 1 calc R U . . .
O1 O -0.07751(10) 0.55482(9) 0.20867(17) 0.0617(4) Uani 1 1 d . . . . .
O2 O 0.12654(10) 0.71850(9) 0.15039(16) 0.0572(4) Uani 1 1 d . . . . .
O3 O -0.20689(11) 0.65903(11) 0.00021(18) 0.0714(5) Uani 1 1 d . . . . .
O4 O -0.15074(10) 0.70562(10) 0.19461(16) 0.0604(4) Uani 1 1 d . . . . .
O5 O 0.01961(13) 0.72542(9) -0.14000(17) 0.0699(5) Uani 1 1 d . . . . .
O6 O 0.07187(12) 0.61057(9) -0.10182(18) 0.0679(5) Uani 1 1 d . . . . .
N1 N -0.04430(17) 0.83802(12) 0.0433(3) 0.0797(7) Uani 1 1 d . . . . .
N2 N -0.11226(15) 0.52264(13) -0.1058(2) 0.0714(6) Uani 1 1 d . . . . .
C2 C -0.01236(13) 0.58590(11) 0.2226(2) 0.0428(5) Uani 1 1 d . . . . .
C3 C 0.00386(12) 0.64612(10) 0.13538(18) 0.0396(4) Uani 1 1 d . . . . .
C4 C 0.09159(13) 0.67064(11) 0.19276(19) 0.0420(5) Uani 1 1 d . . . . .
C5 C 0.20420(15) 0.62192(14) 0.3859(2) 0.0586(6) Uani 1 1 d . . . . .
H5 H 0.2449 0.6532 0.3734 0.070 Uiso 1 1 calc . U . . .
C6 C 0.22092(19) 0.57182(18) 0.4854(3) 0.0750(8) Uani 1 1 d . . . . .
H6 H 0.2735 0.5701 0.5415 0.090 Uiso 1 1 calc . U . . .
C7 C 0.1608(2) 0.52427(17) 0.5030(3) 0.0735(8) Uani 1 1 d . . . . .
H7 H 0.1737 0.4913 0.5710 0.088 Uiso 1 1 calc . U . . .
C8 C 0.08235(16) 0.52477(13) 0.4218(2) 0.0566(6) Uani 1 1 d . . . . .
H8 H 0.0424 0.4920 0.4329 0.068 Uiso 1 1 calc . U . . .
C9 C 0.06453(13) 0.57583(11) 0.32249(19) 0.0424(5) Uani 1 1 d . . . . .
C10 C 0.12516(13) 0.62397(11) 0.30596(19) 0.0437(5) Uani 1 1 d . . . . .
C11 C -0.06534(13) 0.69668(11) 0.0635(2) 0.0438(5) Uani 1 1 d . . . . .
C12 C -0.03072(13) 0.64052(11) -0.00987(19) 0.0432(5) Uani 1 1 d . . . . .
C13 C -0.07862(15) 0.57475(12) -0.0608(2) 0.0514(5) Uani 1 1 d . . . . .
C14 C 0.02365(15) 0.66562(12) -0.0915(2) 0.0496(5) Uani 1 1 d . . . . .
C15 C 0.1274(2) 0.62246(17) -0.1798(3) 0.0782(8) Uani 1 1 d . . . . .
H15D H 0.0964 0.6232 -0.2676 0.117 Uiso 1 1 calc R U . . .
H15E H 0.1670 0.5830 -0.1655 0.117 Uiso 1 1 calc R U . . .
H15F H 0.1553 0.6691 -0.1576 0.117 Uiso 1 1 calc R U . . .
C16 C -0.04934(15) 0.77532(12) 0.0511(2) 0.0531(5) Uani 1 1 d . . . . .
C17 C -0.15039(13) 0.68364(12) 0.0800(2) 0.0485(5) Uani 1 1 d . . . . .
C18 C -0.22541(17) 0.6918(2) 0.2306(3) 0.0814(9) Uani 1 1 d . . . . .
H18D H -0.2711 0.7150 0.1705 0.122 Uiso 1 1 calc R U . . .
H18E H -0.2198 0.7120 0.3135 0.122 Uiso 1 1 calc R U . . .
H18F H -0.2348 0.6392 0.2317 0.122 Uiso 1 1 calc R U . . .


_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
O1A C2A 1.207(3) . ?
O2A C4A 1.205(3) . ?
O3A C17A 1.193(2) . ?
O4A C17A 1.319(2) . ?
O4A C18A 1.451(3) . ?
O5A C14A 1.191(2) . ?
O6A C14A 1.323(2) . ?
O6A C15A 1.435(3) . ?
N1A C16A 1.141(3) . ?
N2A C13A 1.141(2) . ?
C2A C9A 1.480(3) . ?
C2A C3A 1.506(3) . ?
C3A C4A 1.517(3) . ?
C3A C12A 1.537(3) . ?
C3A C11A 1.537(2) . ?
C4A C10A 1.477(3) . ?
C5A C6A 1.378(4) . ?
C5A C10A 1.390(3) . ?
C6A C7A 1.376(5) . ?
C7A C8A 1.396(4) . ?
C8A C9A 1.391(3) . ?
C9A C10A 1.380(3) . ?
C11A C16A 1.451(3) . ?
C11A C12A 1.510(2) . ?
C11A C17A 1.522(3) . ?
C12A C13A 1.450(3) . ?
C12A C14A 1.513(3) . ?
O1 C2 1.207(3) . ?
O2 C4 1.209(2) . ?
O3 C17 1.187(3) . ?
O4 C17 1.321(3) . ?
O4 C18 1.448(3) . ?
O5 C14 1.194(3) . ?
O6 C14 1.308(3) . ?
O6 C15 1.453(3) . ?
N1 C16 1.136(3) . ?
N2 C13 1.135(3) . ?
C2 C9 1.459(3) . ?
C2 C3 1.522(3) . ?
C3 C4 1.507(3) . ?
C3 C11 1.517(3) . ?
C3 C12 1.541(3) . ?
C4 C10 1.475(3) . ?
C5 C10 1.379(3) . ?
C5 C6 1.383(4) . ?
C6 C7 1.384(4) . ?
C7 C8 1.376(4) . ?
C8 C9 1.393(3) . ?
C9 C10 1.393(3) . ?
C11 C16 1.454(3) . ?
C11 C12 1.510(3) . ?
C11 C17 1.519(3) . ?
C12 C13 1.455(3) . ?
C12 C14 1.523(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
C17A O4A C18A 116.00(18) . . ?
C14A O6A C15A 116.31(19) . . ?
O1A C2A C9A 128.1(2) . . ?
O1A C2A C3A 126.24(19) . . ?
C9A C2A C3A 105.66(18) . . ?
C2A C3A C4A 106.86(16) . . ?
C2A C3A C12A 124.66(16) . . ?
C4A C3A C12A 116.29(17) . . ?
C2A C3A C11A 121.46(17) . . ?
C4A C3A C11A 122.65(16) . . ?
C12A C3A C11A 58.84(12) . . ?
O2A C4A C10A 128.3(2) . . ?
O2A C4A C3A 125.66(19) . . ?
C10A C4A C3A 105.97(18) . . ?
C6A C5A C10A 117.0(3) . . ?
C7A C6A C5A 121.4(2) . . ?
C6A C7A C8A 122.1(2) . . ?
C9A C8A C7A 116.6(3) . . ?
C10A C9A C8A 120.9(2) . . ?
C10A C9A C2A 111.19(18) . . ?
C8A C9A C2A 127.9(2) . . ?
C9A C10A C5A 122.1(2) . . ?
C9A C10A C4A 110.29(18) . . ?
C5A C10A C4A 127.6(2) . . ?
C16A C11A C12A 119.10(17) . . ?
C16A C11A C17A 114.44(16) . . ?
C12A C11A C17A 117.63(16) . . ?
C16A C11A C3A 116.18(17) . . ?
C12A C11A C3A 60.58(12) . . ?
C17A C11A C3A 118.55(16) . . ?
C13A C12A C11A 120.99(17) . . ?
C13A C12A C14A 110.89(15) . . ?
C11A C12A C14A 119.74(15) . . ?
C13A C12A C3A 118.31(16) . . ?
C11A C12A C3A 60.58(12) . . ?
C14A C12A C3A 118.06(16) . . ?
N2A C13A C12A 171.1(2) . . ?
O5A C14A O6A 126.4(2) . . ?
O5A C14A C12A 124.90(19) . . ?
O6A C14A C12A 108.72(16) . . ?
N1A C16A C11A 176.6(3) . . ?
O3A C17A O4A 126.6(2) . . ?
O3A C17A C11A 123.74(18) . . ?
O4A C17A C11A 109.67(17) . . ?
C17 O4 C18 116.5(2) . . ?
C14 O6 C15 117.48(19) . . ?
O1 C2 C9 128.9(2) . . ?
O1 C2 C3 124.7(2) . . ?
C9 C2 C3 106.34(17) . . ?
C4 C3 C11 124.61(17) . . ?
C4 C3 C2 106.02(17) . . ?
C11 C3 C2 120.32(17) . . ?
C4 C3 C12 119.69(16) . . ?
C11 C3 C12 59.17(13) . . ?
C2 C3 C12 121.49(16) . . ?
O2 C4 C10 128.0(2) . . ?
O2 C4 C3 125.35(19) . . ?
C10 C4 C3 106.66(16) . . ?
C10 C5 C6 117.9(2) . . ?
C5 C6 C7 121.2(3) . . ?
C8 C7 C6 121.3(2) . . ?
C7 C8 C9 118.0(2) . . ?
C8 C9 C10 120.4(2) . . ?
C8 C9 C2 128.5(2) . . ?
C10 C9 C2 111.04(18) . . ?
C5 C10 C9 121.2(2) . . ?
C5 C10 C4 128.8(2) . . ?
C9 C10 C4 109.90(18) . . ?
C16 C11 C12 119.37(19) . . ?
C16 C11 C3 119.68(19) . . ?
C12 C11 C3 61.18(13) . . ?
C16 C11 C17 111.67(19) . . ?
C12 C11 C17 118.91(17) . . ?
C3 C11 C17 117.67(17) . . ?
C13 C12 C11 119.46(19) . . ?
C13 C12 C14 112.23(18) . . ?
C11 C12 C14 120.37(17) . . ?
C13 C12 C3 117.39(17) . . ?
C11 C12 C3 59.65(13) . . ?
C14 C12 C3 118.30(17) . . ?
N2 C13 C12 175.1(3) . . ?
O5 C14 O6 127.1(2) . . ?
O5 C14 C12 124.2(2) . . ?
O6 C14 C12 108.73(18) . . ?
N1 C16 C11 173.2(3) . . ?
O3 C17 O4 126.7(2) . . ?
O3 C17 C11 124.3(2) . . ?
O4 C17 C11 109.00(18) . . ?

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.077

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: propanol-2'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1432531'
_audit_update_record             
;
2015-10-21 deposited with the CCDC.
2016-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 rubidium 1,1,3,3-tetracyano-2-(2-(isopropoxycarbonyl)benzoyl)prop-2-en-1-ide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H22 N8 O6 Rb2'
_chemical_formula_sum            'C36 H22 N8 O6 Rb2'
_chemical_formula_weight         833.55

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'
Rb Rb -0.9393 2.9676 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   25.935(4)
_cell_length_b                   7.888(2)
_cell_length_c                   18.793(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.37(3)
_cell_angle_gamma                90
_cell_volume                     3648.4(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      14
_cell_measurement_theta_max      17

_exptl_crystal_description       PRISM
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .23
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .11
_exptl_absorpt_coefficient_mu    2.739
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_factor_muR        0.274
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.4852
_exptl_absorpt_correction_T_max  0.7604


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            ?
_diffrn_reflns_av_unetI/netI     0.1231
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.655
_diffrn_reflns_theta_max         25.967
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.517
_diffrn_reflns_point_group_measured_fraction_full 0.518
_reflns_number_total             3695
_reflns_number_gt                1959
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.034
_reflns_Friedel_fraction_max     0.034
_reflns_Friedel_fraction_full    0.035

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0301P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.011(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3695
_refine_ls_number_parameters     473
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_restrained_S_all      0.923
_refine_ls_shift/su_max          0.003
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Rb1 Rb 0.71089(4) -0.3685(2) 0.08836(5) 0.0474(5) Uani 1 1 d . . . . .
Rb2 Rb 0.67036(4) 0.1303(2) 0.07230(5) 0.0503(5) Uani 1 1 d . . . . .
O1 O 0.5803(3) 0.2183(10) 0.1585(4) 0.053(2) Uani 1 1 d . . . . .
O2 O 0.6073(4) 0.4301(15) 0.0483(6) 0.050(3) Uani 1 1 d . . . . .
O3 O 0.5170(4) 0.4299(16) -0.0019(6) 0.053(3) Uani 1 1 d . . . . .
N1 N 0.7134(4) 0.3921(15) 0.2076(5) 0.061(3) Uani 1 1 d . . . . .
N2 N 0.7346(4) 0.2822(16) 0.4454(6) 0.075(4) Uani 1 1 d . . . . .
N3 N 0.4825(5) 0.1636(17) 0.2688(6) 0.080(4) Uani 1 1 d . . . . .
N4 N 0.6191(4) 0.1715(15) 0.4721(6) 0.073(4) Uani 1 1 d . . . . .
C1 C 0.5858(4) 0.3300(14) 0.2047(6) 0.035(3) Uani 1 1 d . . . . .
C2 C 0.5686(4) 0.5056(15) 0.1876(6) 0.037(3) Uani 1 1 d . . . . .
C3 C 0.5529(4) 0.5643(16) 0.1138(6) 0.039(3) Uani 1 1 d . . . . .
C4 C 0.5303(5) 0.7232(18) 0.0958(7) 0.051(3) Uani 1 1 d . . . . .
H4 H 0.5200 0.7600 0.0463 0.061 Uiso 1 1 calc . U . . .
C5 C 0.5226(6) 0.8303(16) 0.1514(8) 0.066(4) Uani 1 1 d . . . . .
H5 H 0.5076 0.9380 0.1401 0.080 Uiso 1 1 calc . U . . .
C6 C 0.5383(7) 0.768(2) 0.2232(10) 0.051(4) Uani 1 1 d . . . . .
H6 H 0.5332 0.8350 0.2610 0.061 Uiso 1 1 calc . U . . .
C7 C 0.5608(5) 0.6139(17) 0.2414(6) 0.047(3) Uani 1 1 d . . . . .
H7 H 0.5713 0.5792 0.2912 0.056 Uiso 1 1 calc . U . . .
C8 C 0.5629(5) 0.4659(15) 0.0526(7) 0.043(3) Uani 1 1 d . . . . .
C9 C 0.5173(5) 0.336(2) -0.0686(7) 0.073(5) Uani 1 1 d . . . . .
H9 H 0.5527 0.3500 -0.0764 0.088 Uiso 1 1 calc R U . . .
C10 C 0.4741(5) 0.4262(19) -0.1309(6) 0.081(5) Uani 1 1 d . . . . .
H10A H 0.4398 0.4189 -0.1216 0.121 Uiso 1 1 calc R U . . .
H10B H 0.4712 0.3739 -0.1781 0.121 Uiso 1 1 calc R U . . .
H10C H 0.4840 0.5432 -0.1322 0.121 Uiso 1 1 calc R U . . .
C11 C 0.5075(7) 0.154(2) -0.0607(10) 0.113(7) Uani 1 1 d . . . . .
H11A H 0.5407 0.0999 -0.0319 0.169 Uiso 1 1 calc R U . . .
H11B H 0.4945 0.1024 -0.1095 0.169 Uiso 1 1 calc R U . . .
H11C H 0.4807 0.1401 -0.0356 0.169 Uiso 1 1 calc R U . . .
C12 C 0.6152(5) 0.2877(14) 0.2880(6) 0.038(3) Uani 1 1 d . . . . .
C13 C 0.6713(5) 0.3197(18) 0.3102(7) 0.054(4) Uani 1 1 d . . . . .
C14 C 0.5845(6) 0.2294(16) 0.3295(6) 0.045(3) Uani 1 1 d . . . . .
C15 C 0.5264(7) 0.199(2) 0.2941(8) 0.048(4) Uani 1 1 d . . . . .
C16 C 0.6046(5) 0.1994(15) 0.4087(8) 0.046(3) Uani 1 1 d . . . . .
C17 C 0.6967(4) 0.3597(19) 0.2542(6) 0.045(3) Uani 1 1 d . . . . .
C18 C 0.7066(5) 0.2980(19) 0.3851(7) 0.054(4) Uani 1 1 d . . . . .
O1A O 0.8039(3) -0.2717(11) 0.2573(5) 0.056(2) Uani 1 1 d . . . . .
O2A O 0.7751(4) -0.0659(15) 0.1218(6) 0.050(3) Uani 1 1 d . . . . .
O3A O 0.8662(4) -0.0692(15) 0.1536(5) 0.044(3) Uani 1 1 d . . . . .
N1A N 0.7640(4) -0.3198(14) 0.5353(6) 0.067(4) Uani 1 1 d . . . . .
N2A N 0.9032(5) -0.3024(16) 0.4546(6) 0.080(4) Uani 1 1 d . . . . .
N3A N 0.6692(4) -0.1154(17) 0.1893(6) 0.067(3) Uani 1 1 d . . . . .
N4A N 0.6483(5) -0.2212(19) 0.4067(6) 0.091(5) Uani 1 1 d . . . . .
C1A C 0.7966(4) -0.1610(16) 0.2980(6) 0.041(3) Uani 1 1 d . . . . .
C2A C 0.8148(4) 0.0160(15) 0.2957(6) 0.038(3) Uani 1 1 d . . . . .
C3A C 0.8270(4) 0.0750(15) 0.2326(6) 0.038(3) Uani 1 1 d . . . . .
C4A C 0.8482(5) 0.2359(17) 0.2321(7) 0.050(3) Uani 1 1 d . . . . .
H4A H 0.8590 0.2715 0.1918 0.060 Uiso 1 1 calc . U . . .
C5A C 0.8532(5) 0.3438(16) 0.2922(8) 0.056(4) Uani 1 1 d . . . . .
H5A H 0.8669 0.4525 0.2912 0.067 Uiso 1 1 calc . U . . .
C6A C 0.8387(6) 0.295(3) 0.3526(9) 0.057(5) Uani 1 1 d . . . . .
H6A H 0.8418 0.3679 0.3925 0.068 Uiso 1 1 calc . U . . .
C7A C 0.8190(4) 0.1316(18) 0.3525(6) 0.049(3) Uani 1 1 d . . . . .
H7A H 0.8079 0.0980 0.3929 0.059 Uiso 1 1 calc . U . . .
C8A C 0.8199(5) -0.0301(15) 0.1629(7) 0.037(3) Uani 1 1 d . . . . .
C9A C 0.8666(4) -0.1702(18) 0.0879(7) 0.056(4) Uani 1 1 d . . . . .
H9A H 0.8338 -0.1430 0.0462 0.068 Uiso 1 1 calc R U . . .
C10A C 0.8647(5) -0.3529(18) 0.1067(8) 0.080(5) Uani 1 1 d . . . . .
H10D H 0.9002 -0.3891 0.1371 0.120 Uiso 1 1 calc R U . . .
H10E H 0.8535 -0.4185 0.0614 0.120 Uiso 1 1 calc R U . . .
H10F H 0.8394 -0.3690 0.1339 0.120 Uiso 1 1 calc R U . . .
C11A C 0.9155(4) -0.1123(19) 0.0676(8) 0.085(5) Uani 1 1 d . . . . .
H11D H 0.9479 -0.1510 0.1049 0.128 Uiso 1 1 calc R U . . .
H11E H 0.9157 0.0092 0.0652 0.128 Uiso 1 1 calc R U . . .
H11F H 0.9139 -0.1584 0.0196 0.128 Uiso 1 1 calc R U . . .
C12A C 0.7680(4) -0.1990(14) 0.3554(6) 0.036(3) Uani 1 1 d . . . . .
C13A C 0.8007(5) -0.2536(17) 0.4251(7) 0.044(3) Uani 1 1 d . . . . .
C14A C 0.7128(4) -0.1814(14) 0.3297(6) 0.035(3) Uani 1 1 d . . . . .
C15A C 0.6874(5) -0.1436(18) 0.2538(8) 0.050(3) Uani 1 1 d . . . . .
C16A C 0.6775(5) -0.206(2) 0.3718(7) 0.055(4) Uani 1 1 d . . . . .
C17A C 0.7792(5) -0.2914(17) 0.4855(8) 0.054(4) Uani 1 1 d . . . . .
C18A C 0.8584(8) -0.282(3) 0.4420(9) 0.062(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Rb1 O2A 2.865(12) . ?
Rb1 N1 2.916(10) 1_545 ?
Rb1 O2 3.006(11) 1_545 ?
Rb1 N2 3.016(11) 2_554 ?
Rb1 N4 3.094(11) 2_554 ?
Rb1 N1A 3.130(11) 2_544 ?
Rb1 N3A 3.170(11) . ?
Rb1 O1A 3.413(9) . ?
Rb1 Rb2 4.060(4) . ?
Rb1 Rb2 4.077(3) 1_545 ?
Rb2 O2 2.830(11) . ?
Rb2 N3A 2.938(12) . ?
Rb2 O2A 3.009(10) . ?
Rb2 N4 3.066(11) 2_554 ?
Rb2 N4A 3.067(11) 2_554 ?
Rb2 N1A 3.111(11) 2_554 ?
Rb2 N1 3.192(11) . ?
Rb2 O1 3.308(8) . ?
Rb2 C17 3.736(12) . ?
Rb2 Rb1 4.077(3) 1_565 ?
O1 C1 1.213(12) . ?
O2 C8 1.212(15) . ?
O2 Rb1 3.006(11) 1_565 ?
O3 C8 1.334(14) . ?
O3 C9 1.461(15) . ?
N1 C17 1.122(13) . ?
N1 Rb1 2.916(10) 1_565 ?
N2 C18 1.144(13) . ?
N2 Rb1 3.016(11) 2 ?
N3 C15 1.121(16) . ?
N4 C16 1.153(14) . ?
N4 Rb2 3.066(11) 2 ?
N4 Rb1 3.094(11) 2 ?
C1 C2 1.460(15) . ?
C1 C12 1.547(14) . ?
C2 C7 1.387(15) . ?
C2 C3 1.395(14) . ?
C3 C4 1.380(16) . ?
C3 C8 1.476(16) . ?
C4 C5 1.405(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.37(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.342(19) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C9 C11 1.474(19) . ?
C9 C10 1.520(17) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C14 1.357(15) . ?
C12 C13 1.406(15) . ?
C13 C18 1.426(16) . ?
C13 C17 1.440(17) . ?
C14 C16 1.432(16) . ?
C14 C15 1.463(18) . ?
O1A C1A 1.215(13) . ?
O2A C8A 1.207(13) . ?
O3A C8A 1.306(13) . ?
O3A C9A 1.472(15) . ?
N1A C17A 1.147(15) . ?
N1A Rb2 3.111(11) 2 ?
N1A Rb1 3.130(11) 2_545 ?
N2A C18A 1.123(17) . ?
N3A C15A 1.176(14) . ?
N4A C16A 1.152(14) . ?
N4A Rb2 3.067(11) 2 ?
C1A C2A 1.479(16) . ?
C1A C12A 1.519(14) . ?
C2A C7A 1.382(15) . ?
C2A C3A 1.400(15) . ?
C3A C4A 1.385(16) . ?
C3A C8A 1.510(15) . ?
C4A C5A 1.387(16) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.36(2) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.38(2) . ?
C6A H6A 0.9300 . ?
C7A H7A 0.9300 . ?
C9A C10A 1.488(16) . ?
C9A C11A 1.506(14) . ?
C9A H9A 0.9800 . ?
C10A H10D 0.9600 . ?
C10A H10E 0.9600 . ?
C10A H10F 0.9600 . ?
C11A H11D 0.9600 . ?
C11A H11E 0.9600 . ?
C11A H11F 0.9600 . ?
C12A C14A 1.366(14) . ?
C12A C13A 1.386(15) . ?
C13A C17A 1.444(17) . ?
C13A C18A 1.446(19) . ?
C14A C16A 1.400(16) . ?
C14A C15A 1.402(17) . ?

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
O2A Rb1 N1 120.0(3) . 1_545 ?
O2A Rb1 O2 155.1(3) . 1_545 ?
N1 Rb1 O2 69.6(3) 1_545 1_545 ?
O2A Rb1 N2 74.9(3) . 2_554 ?
N1 Rb1 N2 150.4(4) 1_545 2_554 ?
O2 Rb1 N2 108.3(3) 1_545 2_554 ?
O2A Rb1 N4 90.1(3) . 2_554 ?
N1 Rb1 N4 133.9(3) 1_545 2_554 ?
O2 Rb1 N4 70.1(3) 1_545 2_554 ?
N2 Rb1 N4 65.5(3) 2_554 2_554 ?
O2A Rb1 N1A 116.1(3) . 2_544 ?
N1 Rb1 N1A 80.3(3) 1_545 2_544 ?
O2 Rb1 N1A 87.4(3) 1_545 2_544 ?
N2 Rb1 N1A 70.1(3) 2_554 2_544 ?
N4 Rb1 N1A 119.2(3) 2_554 2_544 ?
O2A Rb1 N3A 68.2(3) . . ?
N1 Rb1 N3A 82.9(3) 1_545 . ?
O2 Rb1 N3A 92.0(3) 1_545 . ?
N2 Rb1 N3A 126.5(3) 2_554 . ?
N4 Rb1 N3A 77.0(3) 2_554 . ?
N1A Rb1 N3A 162.3(3) 2_544 . ?
O2A Rb1 O1A 54.4(3) . . ?
N1 Rb1 O1A 65.9(2) 1_545 . ?
O2 Rb1 O1A 131.7(3) 1_545 . ?
N2 Rb1 O1A 119.7(2) 2_554 . ?
N4 Rb1 O1A 134.8(3) 2_554 . ?
N1A Rb1 O1A 102.7(3) 2_544 . ?
N3A Rb1 O1A 65.0(2) . . ?
O2A Rb1 Rb2 47.8(2) . . ?
N1 Rb1 Rb2 128.9(2) 1_545 . ?
O2 Rb1 Rb2 107.7(2) 1_545 . ?
N2 Rb1 Rb2 80.5(2) 2_554 . ?
N4 Rb1 Rb2 48.5(2) 2_554 . ?
N1A Rb1 Rb2 150.1(2) 2_544 . ?
N3A Rb1 Rb2 45.9(2) . . ?
O1A Rb1 Rb2 86.72(15) . . ?
O2A Rb1 Rb2 160.5(2) . 1_545 ?
N1 Rb1 Rb2 51.1(2) 1_545 1_545 ?
O2 Rb1 Rb2 43.9(2) 1_545 1_545 ?
N2 Rb1 Rb2 105.8(2) 2_554 1_545 ?
N4 Rb1 Rb2 108.2(2) 2_554 1_545 ?
N1A Rb1 Rb2 49.0(2) 2_544 1_545 ?
N3A Rb1 Rb2 121.8(2) . 1_545 ?
O1A Rb1 Rb2 112.08(15) . 1_545 ?
Rb2 Rb1 Rb2 151.59(4) . 1_545 ?
O2 Rb2 N3A 121.9(3) . . ?
O2 Rb2 O2A 154.1(3) . . ?
N3A Rb2 O2A 69.5(3) . . ?
O2 Rb2 N4 115.7(3) . 2_554 ?
N3A Rb2 N4 80.9(3) . 2_554 ?
O2A Rb2 N4 88.0(3) . 2_554 ?
O2 Rb2 N4A 74.3(3) . 2_554 ?
N3A Rb2 N4A 150.6(4) . 2_554 ?
O2A Rb2 N4A 107.2(3) . 2_554 ?
N4 Rb2 N4A 69.7(4) 2_554 2_554 ?
O2 Rb2 N1A 90.9(3) . 2_554 ?
N3A Rb2 N1A 132.6(3) . 2_554 ?
O2A Rb2 N1A 67.9(3) . 2_554 ?
N4 Rb2 N1A 117.0(3) 2_554 2_554 ?
N4A Rb2 N1A 64.5(3) 2_554 2_554 ?
O2 Rb2 N1 68.0(3) . . ?
N3A Rb2 N1 85.1(3) . . ?
O2A Rb2 N1 91.8(3) . . ?
N4 Rb2 N1 165.1(3) 2_554 . ?
N4A Rb2 N1 124.3(3) 2_554 . ?
N1A Rb2 N1 76.4(3) 2_554 . ?
O2 Rb2 O1 56.0(3) . . ?
N3A Rb2 O1 66.2(2) . . ?
O2A Rb2 O1 131.6(3) . . ?
N4 Rb2 O1 103.1(3) 2_554 . ?
N4A Rb2 O1 120.9(3) 2_554 . ?
N1A Rb2 O1 136.9(3) 2_554 . ?
N1 Rb2 O1 66.3(2) . . ?
O2 Rb2 C17 70.8(3) . . ?
N3A Rb2 C17 71.1(3) . . ?
O2A Rb2 C17 94.6(3) . . ?
N4 Rb2 C17 149.0(3) 2_554 . ?
N4A Rb2 C17 137.5(4) 2_554 . ?
N1A Rb2 C17 92.4(3) 2_554 . ?
N1 Rb2 C17 16.3(2) . . ?
O1 Rb2 C17 53.4(2) . . ?
O2 Rb2 Rb1 160.9(2) . . ?
N3A Rb2 Rb1 50.8(2) . . ?
O2A Rb2 Rb1 44.8(2) . . ?
N4 Rb2 Rb1 49.1(2) 2_554 . ?
N4A Rb2 Rb1 105.2(3) 2_554 . ?
N1A Rb2 Rb1 106.3(2) 2_554 . ?
N1 Rb2 Rb1 123.40(19) . . ?
O1 Rb2 Rb1 111.91(15) . . ?
C17 Rb2 Rb1 115.7(2) . . ?
O2 Rb2 Rb1 47.5(2) . 1_565 ?
N3A Rb2 Rb1 130.3(2) . 1_565 ?
O2A Rb2 Rb1 106.8(2) . 1_565 ?
N4 Rb2 Rb1 148.2(2) 2_554 1_565 ?
N4A Rb2 Rb1 79.0(3) 2_554 1_565 ?
N1A Rb2 Rb1 49.4(2) 2_554 1_565 ?
N1 Rb2 Rb1 45.30(18) . 1_565 ?
O1 Rb2 Rb1 88.04(15) . 1_565 ?
C17 Rb2 Rb1 59.6(2) . 1_565 ?
Rb1 Rb2 Rb1 151.60(4) . 1_565 ?
C1 O1 Rb2 124.2(7) . . ?
C8 O2 Rb2 134.2(10) . . ?
C8 O2 Rb1 130.8(10) . 1_565 ?
Rb2 O2 Rb1 88.6(3) . 1_565 ?
C8 O3 C9 121.4(11) . . ?
C17 N1 Rb1 145.7(11) . 1_565 ?
C17 N1 Rb2 110.5(10) . . ?
Rb1 N1 Rb2 83.6(2) 1_565 . ?
C18 N2 Rb1 127.9(10) . 2 ?
C16 N4 Rb2 136.0(11) . 2 ?
C16 N4 Rb1 124.2(10) . 2 ?
Rb2 N4 Rb1 82.4(3) 2 2 ?
O1 C1 C2 125.0(10) . . ?
O1 C1 C12 118.5(10) . . ?
C2 C1 C12 116.5(10) . . ?
C7 C2 C3 117.2(11) . . ?
C7 C2 C1 121.9(11) . . ?
C3 C2 C1 120.4(11) . . ?
C4 C3 C2 120.8(11) . . ?
C4 C3 C8 116.9(11) . . ?
C2 C3 C8 122.1(11) . . ?
C3 C4 C5 120.9(11) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 116.5(12) . . ?
C6 C5 H5 121.7 . . ?
C4 C5 H5 121.7 . . ?
C7 C6 C5 123.1(15) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C6 C7 C2 121.5(12) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
O2 C8 O3 122.4(13) . . ?
O2 C8 C3 125.3(12) . . ?
O3 C8 C3 112.1(11) . . ?
O3 C9 C11 111.1(13) . . ?
O3 C9 C10 102.6(12) . . ?
C11 C9 C10 115.2(13) . . ?
O3 C9 H9 109.2 . . ?
C11 C9 H9 109.2 . . ?
C10 C9 H9 109.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C12 C13 129.1(11) . . ?
C14 C12 C1 117.6(10) . . ?
C13 C12 C1 113.3(10) . . ?
C12 C13 C18 123.6(11) . . ?
C12 C13 C17 119.4(10) . . ?
C18 C13 C17 116.7(10) . . ?
C12 C14 C16 124.4(12) . . ?
C12 C14 C15 120.0(12) . . ?
C16 C14 C15 115.6(12) . . ?
N3 C15 C14 174.5(18) . . ?
N4 C16 C14 177.5(14) . . ?
N1 C17 C13 175.9(12) . . ?
N1 C17 Rb2 53.1(9) . . ?
C13 C17 Rb2 124.6(9) . . ?
N2 C18 C13 179.1(18) . . ?
C1A O1A Rb1 122.9(7) . . ?
C8A O2A Rb1 135.3(9) . . ?
C8A O2A Rb2 132.0(10) . . ?
Rb1 O2A Rb2 87.4(3) . . ?
C8A O3A C9A 119.3(10) . . ?
C17A N1A Rb2 125.6(10) . 2 ?
C17A N1A Rb1 135.5(11) . 2_545 ?
Rb2 N1A Rb1 81.6(3) 2 2_545 ?
C15A N3A Rb2 143.3(12) . . ?
C15A N3A Rb1 113.3(10) . . ?
Rb2 N3A Rb1 83.2(3) . . ?
C16A N4A Rb2 127.4(9) . 2 ?
O1A C1A C2A 123.1(10) . . ?
O1A C1A C12A 120.9(11) . . ?
C2A C1A C12A 116.0(10) . . ?
C7A C2A C3A 116.9(11) . . ?
C7A C2A C1A 123.2(12) . . ?
C3A C2A C1A 119.8(11) . . ?
C4A C3A C2A 120.4(11) . . ?
C4A C3A C8A 116.0(11) . . ?
C2A C3A C8A 123.6(11) . . ?
C3A C4A C5A 119.5(12) . . ?
C3A C4A H4A 120.2 . . ?
C5A C4A H4A 120.2 . . ?
C6A C5A C4A 121.6(14) . . ?
C6A C5A H5A 119.2 . . ?
C4A C5A H5A 119.2 . . ?
C5A C6A C7A 117.7(15) . . ?
C5A C6A H6A 121.2 . . ?
C7A C6A H6A 121.2 . . ?
C2A C7A C6A 123.5(13) . . ?
C2A C7A H7A 118.2 . . ?
C6A C7A H7A 118.2 . . ?
O2A C8A O3A 126.7(13) . . ?
O2A C8A C3A 120.9(11) . . ?
O3A C8A C3A 112.3(10) . . ?
O3A C9A C10A 108.4(11) . . ?
O3A C9A C11A 106.0(10) . . ?
C10A C9A C11A 116.5(12) . . ?
O3A C9A H9A 108.6 . . ?
C10A C9A H9A 108.6 . . ?
C11A C9A H9A 108.6 . . ?
C9A C10A H10D 109.5 . . ?
C9A C10A H10E 109.5 . . ?
H10D C10A H10E 109.5 . . ?
C9A C10A H10F 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C9A C11A H11D 109.5 . . ?
C9A C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
C9A C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
C14A C12A C13A 128.7(11) . . ?
C14A C12A C1A 115.0(9) . . ?
C13A C12A C1A 116.2(10) . . ?
C12A C13A C17A 122.3(11) . . ?
C12A C13A C18A 122.5(13) . . ?
C17A C13A C18A 115.2(13) . . ?
C12A C14A C16A 125.9(10) . . ?
C12A C14A C15A 119.0(10) . . ?
C16A C14A C15A 115.0(10) . . ?
N3A C15A C14A 175.6(13) . . ?
N4A C16A C14A 177.7(18) . . ?
N1A C17A C13A 177.5(15) . . ?
N2A C18A C13A 179(2) . . ?

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
Rb2 O1 C1 C2 88.5(12) . . . . ?
Rb2 O1 C1 C12 -88.8(11) . . . . ?
O1 C1 C2 C7 160.4(12) . . . . ?
C12 C1 C2 C7 -22.2(15) . . . . ?
O1 C1 C2 C3 -11.5(17) . . . . ?
C12 C1 C2 C3 165.8(10) . . . . ?
C7 C2 C3 C4 -0.4(16) . . . . ?
C1 C2 C3 C4 172.0(10) . . . . ?
C7 C2 C3 C8 175.3(11) . . . . ?
C1 C2 C3 C8 -12.4(16) . . . . ?
C2 C3 C4 C5 0.1(18) . . . . ?
C8 C3 C4 C5 -175.8(12) . . . . ?
C3 C4 C5 C6 0(2) . . . . ?
C4 C5 C6 C7 1(2) . . . . ?
C5 C6 C7 C2 -1(2) . . . . ?
C3 C2 C7 C6 1.0(19) . . . . ?
C1 C2 C7 C6 -171.2(13) . . . . ?
Rb2 O2 C8 O3 -80.6(17) . . . . ?
Rb1 O2 C8 O3 136.8(11) 1_565 . . . ?
Rb2 O2 C8 C3 104.5(15) . . . . ?
Rb1 O2 C8 C3 -38.0(19) 1_565 . . . ?
C9 O3 C8 O2 4(2) . . . . ?
C9 O3 C8 C3 179.1(13) . . . . ?
C4 C3 C8 O2 112.0(15) . . . . ?
C2 C3 C8 O2 -63.8(18) . . . . ?
C4 C3 C8 O3 -63.3(14) . . . . ?
C2 C3 C8 O3 120.9(12) . . . . ?
C8 O3 C9 C11 96.1(16) . . . . ?
C8 O3 C9 C10 -140.3(12) . . . . ?
O1 C1 C12 C14 -89.0(13) . . . . ?
C2 C1 C12 C14 93.4(13) . . . . ?
O1 C1 C12 C13 92.1(14) . . . . ?
C2 C1 C12 C13 -85.4(12) . . . . ?
C14 C12 C13 C18 -2(2) . . . . ?
C1 C12 C13 C18 177.0(13) . . . . ?
C14 C12 C13 C17 171.6(13) . . . . ?
C1 C12 C13 C17 -9.7(17) . . . . ?
C13 C12 C14 C16 5(2) . . . . ?
C1 C12 C14 C16 -174.1(11) . . . . ?
C13 C12 C14 C15 -177.8(14) . . . . ?
C1 C12 C14 C15 3.5(18) . . . . ?
Rb1 N1 C17 Rb2 109.8(17) 1_565 . . . ?
C12 C13 C17 Rb2 -44.5(17) . . . . ?
C18 C13 C17 Rb2 129.2(12) . . . . ?
Rb1 O1A C1A C2A -92.2(11) . . . . ?
Rb1 O1A C1A C12A 88.2(11) . . . . ?
O1A C1A C2A C7A -163.6(12) . . . . ?
C12A C1A C2A C7A 16.1(15) . . . . ?
O1A C1A C2A C3A 18.7(16) . . . . ?
C12A C1A C2A C3A -161.7(10) . . . . ?
C7A C2A C3A C4A 7.3(16) . . . . ?
C1A C2A C3A C4A -174.8(10) . . . . ?
C7A C2A C3A C8A -174.5(10) . . . . ?
C1A C2A C3A C8A 3.3(16) . . . . ?
C2A C3A C4A C5A -5.3(17) . . . . ?
C8A C3A C4A C5A 176.5(11) . . . . ?
C3A C4A C5A C6A 1(2) . . . . ?
C4A C5A C6A C7A 1(2) . . . . ?
C3A C2A C7A C6A -5.7(18) . . . . ?
C1A C2A C7A C6A 176.5(12) . . . . ?
C5A C6A C7A C2A 2(2) . . . . ?
Rb1 O2A C8A O3A 74.0(18) . . . . ?
Rb2 O2A C8A O3A -140.5(12) . . . . ?
Rb1 O2A C8A C3A -107.9(14) . . . . ?
Rb2 O2A C8A C3A 37.5(18) . . . . ?
C9A O3A C8A O2A -1(2) . . . . ?
C9A O3A C8A C3A -179.5(11) . . . . ?
C4A C3A C8A O2A -112.0(14) . . . . ?
C2A C3A C8A O2A 69.7(16) . . . . ?
C4A C3A C8A O3A 66.2(14) . . . . ?
C2A C3A C8A O3A -112.0(12) . . . . ?
C8A O3A C9A C10A -86.0(14) . . . . ?
C8A O3A C9A C11A 148.2(12) . . . . ?
O1A C1A C12A C14A -89.1(14) . . . . ?
C2A C1A C12A C14A 91.2(12) . . . . ?
O1A C1A C12A C13A 88.2(14) . . . . ?
C2A C1A C12A C13A -91.5(13) . . . . ?
C14A C12A C13A C17A -4(2) . . . . ?
C1A C12A C13A C17A 178.8(12) . . . . ?
C14A C12A C13A C18A 173.8(15) . . . . ?
C1A C12A C13A C18A -3(2) . . . . ?
C13A C12A C14A C16A 4(2) . . . . ?
C1A C12A C14A C16A -178.9(13) . . . . ?
C13A C12A C14A C15A -172.3(13) . . . . ?
C1A C12A C14A C15A 4.6(16) . . . . ?

_refine_diff_density_max         0.430
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.085

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: propanol-2'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1432532'
_audit_update_record             
;
2015-10-21 deposited with the CCDC.
2016-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 potassium (Z)-2,4-dicyano-1,5-dimethoxy-3-(2-(methoxycarbonyl)benzoyl)-1,5-dioxopent-3-en-2-ide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 K N2 O7'
_chemical_formula_sum            'C18 H13 K N2 O7'
_chemical_formula_weight         408.40

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'
K K 0.2009 0.2494 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.498(5)
_cell_length_b                   13.886(4)
_cell_length_c                   18.696(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3764.1(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      13
_cell_measurement_theta_max      18

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             1680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .15
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_factor_muR        0.031
_exptl_absorpt_process_details   
;
Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.6614
_exptl_absorpt_correction_T_max  0.9693


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            ?
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.179
_diffrn_reflns_theta_max         26.965
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4085
_reflns_number_gt                2507
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+0.7826P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4085
_refine_ls_number_parameters     267
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
K1 K 0.18854(5) 0.59860(5) 0.08436(3) 0.04247(19) Uani 1 1 d . . . . .
O1 O 0.35241(15) 0.59206(15) 0.15492(11) 0.0442(5) Uani 1 1 d . . . . .
O2 O 0.43013(16) 0.67652(14) 0.23731(12) 0.0509(6) Uani 1 1 d . . . . .
O3 O 0.25127(14) 0.41213(14) 0.15740(10) 0.0405(5) Uani 1 1 d . . . . .
O4 O 0.33706(15) 0.22474(15) 0.20499(11) 0.0460(6) Uani 1 1 d . . . . .
O5 O 0.33802(17) 0.18725(15) 0.32174(11) 0.0512(6) Uani 1 1 d . . . . .
O6 O 0.23760(16) 0.26248(15) 0.03741(12) 0.0537(6) Uani 1 1 d . . . . .
O7 O 0.22459(18) 0.41408(16) 0.00024(12) 0.0616(7) Uani 1 1 d D . . . .
N1 N 0.51932(19) 0.5360(2) 0.36387(14) 0.0552(8) Uani 1 1 d . . . . .
N2 N 0.3638(2) 0.3758(2) 0.42749(14) 0.0625(9) Uani 1 1 d . . . . .
C1 C 0.39342(19) 0.5953(2) 0.21150(15) 0.0357(6) Uani 1 1 d . . . . .
C2 C 0.40736(19) 0.5138(2) 0.25912(14) 0.0333(6) Uani 1 1 d . . . . .
C3 C 0.36972(18) 0.42347(19) 0.24370(14) 0.0305(6) Uani 1 1 d . . . . .
C4 C 0.3608(2) 0.3472(2) 0.29158(14) 0.0332(6) Uani 1 1 d . . . . .
C5 C 0.3432(2) 0.2496(2) 0.26660(16) 0.0355(7) Uani 1 1 d . . . . .
C6 C 0.3646(2) 0.3628(2) 0.36670(17) 0.0439(8) Uani 1 1 d . . . . .
C7 C 0.4662(2) 0.5272(2) 0.31865(15) 0.0377(7) Uani 1 1 d . . . . .
C8 C 0.4117(3) 0.7626(2) 0.1962(2) 0.0633(10) Uani 1 1 d . . . . .
H8A H 0.4478 0.7617 0.1532 0.095 Uiso 1 1 calc R U . . .
H8B H 0.4275 0.8183 0.2240 0.095 Uiso 1 1 calc R U . . .
H8C H 0.3474 0.7650 0.1840 0.095 Uiso 1 1 calc R U . . .
C9 C 0.3284(3) 0.0870(2) 0.30362(19) 0.0578(10) Uani 1 1 d . . . . .
H9A H 0.2719 0.0775 0.2778 0.087 Uiso 1 1 calc R U . . .
H9B H 0.3275 0.0492 0.3466 0.087 Uiso 1 1 calc R U . . .
H9C H 0.3795 0.0674 0.2744 0.087 Uiso 1 1 calc R U . . .
C10 C 0.33351(19) 0.4073(2) 0.16820(14) 0.0322(6) Uani 1 1 d . . . . .
C11 C 0.2712(2) 0.3405(2) 0.02800(16) 0.0441(8) Uani 1 1 d . . . . .
C12 C 0.1276(4) 0.3930(4) -0.0142(4) 0.0985(19) Uani 1 1 d . . . . .
C13 C 0.40138(19) 0.3887(2) 0.11045(14) 0.0341(7) Uani 1 1 d . . . . .
C14 C 0.4953(2) 0.3963(3) 0.12196(16) 0.0466(8) Uani 1 1 d . . . . .
H14 H 0.5168 0.4109 0.1676 0.056 Uiso 1 1 calc . U . . .
C15 C 0.5579(3) 0.3829(3) 0.06713(19) 0.0585(10) Uani 1 1 d . . . . .
H15 H 0.6209 0.3891 0.0757 0.070 Uiso 1 1 calc . U . . .
C16 C 0.5265(3) 0.3603(3) 0.0002(2) 0.0638(11) Uani 1 1 d . . . . .
H16 H 0.5681 0.3519 -0.0371 0.077 Uiso 1 1 calc . U . . .
C17 C 0.4336(3) 0.3501(2) -0.01207(16) 0.0555(9) Uani 1 1 d . . . . .
H17 H 0.4131 0.3340 -0.0576 0.067 Uiso 1 1 calc . U . . .
C18 C 0.3703(2) 0.3635(2) 0.04216(15) 0.0377(7) Uani 1 1 d . . . . .
H12 H 0.102(3) 0.455(3) -0.032(2) 0.101(15) Uiso 1 1 d . . . . .
H121 H 0.135(2) 0.346(3) -0.0624(15) 0.123(19) Uiso 1 1 d D . . . .
H122 H 0.099(4) 0.362(4) 0.0213(19) 0.18(3) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
K1 O6 2.664(2) 7_665 ?
K1 O1 2.719(2) . ?
K1 N1 2.777(3) 6_556 ?
K1 O4 2.880(2) 7_665 ?
K1 N2 3.050(3) 2_564 ?
K1 O7 3.052(3) . ?
K1 O3 3.065(2) . ?
K1 C12 3.511(5) . ?
O1 C1 1.214(3) . ?
O2 C1 1.337(3) . ?
O2 C8 1.447(4) . ?
O3 C10 1.211(3) . ?
O4 C5 1.206(3) . ?
O4 K1 2.880(2) 7_655 ?
O5 C5 1.348(3) . ?
O5 C9 1.439(4) . ?
O6 C11 1.201(4) . ?
O6 K1 2.664(2) 7_655 ?
O7 C11 1.330(4) . ?
O7 C12 1.461(6) . ?
N1 C7 1.150(4) . ?
N1 K1 2.777(3) 6_656 ?
N2 C6 1.151(4) . ?
N2 K1 3.050(3) 2_565 ?
C1 C2 1.454(4) . ?
C2 C3 1.398(4) . ?
C2 C7 1.415(4) . ?
C3 C4 1.393(4) . ?
C3 C10 1.523(3) . ?
C4 C6 1.422(4) . ?
C4 C5 1.457(4) . ?
C10 C13 1.484(4) . ?
C11 C18 1.495(5) . ?
C13 C14 1.382(4) . ?
C13 C18 1.399(4) . ?
C14 C15 1.383(4) . ?
C15 C16 1.369(5) . ?
C16 C17 1.373(5) . ?
C17 C18 1.381(4) . ?

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
O6 K1 O1 80.63(7) 7_665 . ?
O6 K1 N1 137.52(9) 7_665 6_556 ?
O1 K1 N1 126.33(8) . 6_556 ?
O6 K1 O4 77.89(7) 7_665 7_665 ?
O1 K1 O4 75.70(7) . 7_665 ?
N1 K1 O4 78.68(8) 6_556 7_665 ?
O6 K1 N2 71.56(8) 7_665 2_564 ?
O1 K1 N2 133.45(8) . 2_564 ?
N1 K1 N2 98.73(9) 6_556 2_564 ?
O4 K1 N2 130.56(8) 7_665 2_564 ?
O6 K1 O7 118.59(7) 7_665 . ?
O1 K1 O7 94.15(7) . . ?
N1 K1 O7 93.90(8) 6_556 . ?
O4 K1 O7 159.47(6) 7_665 . ?
N2 K1 O7 69.19(7) 2_564 . ?
O6 K1 O3 138.52(7) 7_665 . ?
O1 K1 O3 59.76(6) . . ?
N1 K1 O3 80.93(8) 6_556 . ?
O4 K1 O3 101.72(6) 7_665 . ?
N2 K1 O3 126.91(7) 2_564 . ?
O7 K1 O3 57.97(6) . . ?
O6 K1 C12 128.51(14) 7_665 . ?
O1 K1 C12 116.58(9) . . ?
N1 K1 C12 72.92(14) 6_556 . ?
O4 K1 C12 150.85(14) 7_665 . ?
N2 K1 C12 61.79(12) 2_564 . ?
O7 K1 C12 24.46(11) . . ?
O3 K1 C12 67.78(10) . . ?
C1 O1 K1 148.12(19) . . ?
C1 O2 C8 115.6(2) . . ?
C10 O3 K1 114.42(18) . . ?
C5 O4 K1 158.7(2) . 7_655 ?
C5 O5 C9 116.5(2) . . ?
C11 O6 K1 131.0(2) . 7_655 ?
C11 O7 C12 114.0(3) . . ?
C11 O7 K1 122.05(18) . . ?
C12 O7 K1 95.7(3) . . ?
C7 N1 K1 151.8(2) . 6_656 ?
C6 N2 K1 166.1(3) . 2_565 ?
O1 C1 O2 122.7(3) . . ?
O1 C1 C2 124.9(3) . . ?
O2 C1 C2 112.3(2) . . ?
C3 C2 C7 121.0(3) . . ?
C3 C2 C1 121.2(2) . . ?
C7 C2 C1 117.6(3) . . ?
C4 C3 C2 125.9(2) . . ?
C4 C3 C10 116.8(2) . . ?
C2 C3 C10 117.3(2) . . ?
C3 C4 C6 121.0(3) . . ?
C3 C4 C5 121.2(2) . . ?
C6 C4 C5 117.7(3) . . ?
O4 C5 O5 122.9(3) . . ?
O4 C5 C4 125.8(3) . . ?
O5 C5 C4 111.2(2) . . ?
N2 C6 C4 177.1(4) . . ?
N1 C7 C2 175.0(3) . . ?
O3 C10 C13 122.8(2) . . ?
O3 C10 C3 119.1(2) . . ?
C13 C10 C3 118.1(2) . . ?
O6 C11 O7 123.0(3) . . ?
O6 C11 C18 123.8(3) . . ?
O7 C11 C18 113.1(3) . . ?
O7 C12 K1 59.9(2) . . ?
C14 C13 C18 118.6(3) . . ?
C14 C13 C10 121.8(3) . . ?
C18 C13 C10 119.6(3) . . ?
C13 C14 C15 121.4(3) . . ?
C16 C15 C14 119.3(3) . . ?
C15 C16 C17 120.2(3) . . ?
C16 C17 C18 121.1(3) . . ?
C17 C18 C13 119.3(3) . . ?
C17 C18 C11 118.7(3) . . ?
C13 C18 C11 121.7(3) . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_preparation       Luminescent
