# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Colin Seaton'
_publ_contact_author_email       COLIN.SEATON@MANCHESTER.AC.UK

_publ_section_title              
;
Formation of a hybrid coordination-molecular complex
;
loop_
_publ_author_name
'Colin Seaton'
'Nicholas Blagden'
'Ian Scowen'

# Attachment 'CS_LiBz1_0m.cif'

data_cs_libz1_0m
_database_code_depnum_ccdc_archive 'CCDC 716996'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
lithium [triaqua (3,5-dinitrobenzoate) (4-(dimethylamino)benzoate)]
;
_chemical_name_common            
;lithium (triaqua (3,5-dinitrobenzoate) (4-
(dimethylamino)benzoate))
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 Li2 N3 O11'
_chemical_formula_weight         443.22

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'
Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   6.4134(6)
_cell_length_b                   7.4639(7)
_cell_length_c                   40.105(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.439(4)
_cell_angle_gamma                90.00
_cell_volume                     1914.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      29.10

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.354
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            42717
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_limit_l_max       55
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         29.31
_reflns_number_total             5185
_reflns_number_gt                4248
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.8338P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5185
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1585
_refine_ls_wR_factor_gt          0.1489
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001

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
C5A C -0.1997(2) 0.1180(2) 0.14044(4) 0.0165(3) Uani 1 1 d . . .
H5A H -0.2996 0.0701 0.1543 0.020 Uiso 1 1 calc R . .
C3A C 0.1408(2) 0.2389(2) 0.13374(4) 0.0167(3) Uani 1 1 d . . .
H3A H 0.2752 0.2747 0.1430 0.020 Uiso 1 1 calc R . .
C4A C -0.0025(2) 0.1676(2) 0.15475(4) 0.0143(3) Uani 1 1 d . . .
C6A C -0.2527(2) 0.1373(2) 0.10650(4) 0.0185(3) Uani 1 1 d . . .
H6A H -0.3883 0.1034 0.0975 0.022 Uiso 1 1 calc R . .
C2A C 0.0906(2) 0.2583(2) 0.09980(4) 0.0178(3) Uani 1 1 d . . .
H2A H 0.1908 0.3071 0.0861 0.021 Uiso 1 1 calc R . .
C1A C -0.1082(2) 0.2065(2) 0.08522(4) 0.0172(3) Uani 1 1 d . . .
C7A C 0.0545(2) 0.1362(2) 0.19086(4) 0.0141(3) Uani 1 1 d . . .
C9A C -0.3457(3) 0.1394(3) 0.03604(5) 0.0299(4) Uani 1 1 d . . .
H9A1 H -0.3261 0.0093 0.0371 0.045 Uiso 1 1 calc R . .
H9A2 H -0.3683 0.1768 0.0126 0.045 Uiso 1 1 calc R . .
H9A3 H -0.4676 0.1726 0.0480 0.045 Uiso 1 1 calc R . .
C8A C -0.0016(3) 0.2745(3) 0.02919(5) 0.0329(5) Uani 1 1 d . . .
H8A1 H 0.0757 0.3799 0.0379 0.049 Uiso 1 1 calc R . .
H8A2 H -0.0681 0.3015 0.0069 0.049 Uiso 1 1 calc R . .
H8A3 H 0.0951 0.1737 0.0277 0.049 Uiso 1 1 calc R . .
N1A N -0.1606(2) 0.2279(2) 0.05143(4) 0.0240(3) Uani 1 1 d . . .
O1A O 0.23368(17) 0.18633(17) 0.20360(3) 0.0179(3) Uani 1 1 d . . .
O2A O -0.07404(18) 0.05850(17) 0.20820(3) 0.0186(3) Uani 1 1 d . . .
O1 O 0.67854(18) 0.32136(18) 0.23467(3) 0.0174(3) Uani 1 1 d . . .
O2 O 0.25326(19) 0.58833(18) 0.22669(3) 0.0200(3) Uani 1 1 d . . .
Li1 Li 0.4090(4) 0.3897(4) 0.20782(7) 0.0192(6) Uani 1 1 d . . .
C4B C 0.8013(2) 0.6138(2) 0.13886(4) 0.0139(3) Uani 1 1 d . . .
C5B C 0.6743(2) 0.5780(2) 0.11003(4) 0.0159(3) Uani 1 1 d . . .
H5B H 0.5438 0.5192 0.1113 0.019 Uiso 1 1 calc R . .
C7B C 0.7215(2) 0.5639(2) 0.17197(4) 0.0139(3) Uani 1 1 d . . .
C6B C 0.7401(2) 0.6291(2) 0.07951(4) 0.0170(3) Uani 1 1 d . . .
C2B C 1.0520(2) 0.7455(2) 0.10553(4) 0.0167(3) Uani 1 1 d . . .
C1B C 0.9289(2) 0.7140(2) 0.07631(4) 0.0186(3) Uani 1 1 d . . .
H1B H 0.9719 0.7488 0.0551 0.022 Uiso 1 1 calc R . .
C3B C 0.9933(2) 0.6982(2) 0.13674(4) 0.0159(3) Uani 1 1 d . . .
H3B H 1.0818 0.7227 0.1563 0.019 Uiso 1 1 calc R . .
O2B O 0.83475(17) 0.60452(16) 0.19863(3) 0.0159(2) Uani 1 1 d . . .
O1B O 0.55052(17) 0.48646(18) 0.17133(3) 0.0190(3) Uani 1 1 d . . .
O3 O -0.5074(2) -0.1169(2) 0.20700(4) 0.0277(3) Uani 1 1 d . . .
N2B N 0.6019(2) 0.5970(2) 0.04921(4) 0.0225(3) Uani 1 1 d . . .
N1B N 1.2518(2) 0.8380(2) 0.10310(4) 0.0215(3) Uani 1 1 d . . .
O11B O 1.36207(19) 0.8636(2) 0.12890(4) 0.0291(3) Uani 1 1 d . . .
O12B O 1.2982(2) 0.8854(2) 0.07523(4) 0.0329(3) Uani 1 1 d . . .
O21B O 0.4326(2) 0.5260(2) 0.05250(3) 0.0315(3) Uani 1 1 d . . .
O22B O 0.6626(2) 0.6441(2) 0.02250(3) 0.0352(4) Uani 1 1 d . . .
Li2 Li -0.2171(4) -0.1546(4) 0.21643(7) 0.0181(5) Uani 1 1 d . . .
H21 H 0.262(4) 0.606(4) 0.2479(7) 0.035(7) Uiso 1 1 d . . .
H22 H 0.126(4) 0.593(4) 0.2209(7) 0.042(7) Uiso 1 1 d . . .
H11 H 0.739(4) 0.412(4) 0.2261(7) 0.042(7) Uiso 1 1 d . . .
H12 H 0.761(5) 0.228(5) 0.2280(8) 0.064(10) Uiso 1 1 d . . .
H32 H -0.601(5) -0.205(5) 0.2120(8) 0.066(10) Uiso 1 1 d . . .
H31 H -0.577(5) -0.019(5) 0.2049(8) 0.052(8) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C5A C6A 1.385(2) . ?
C5A C4A 1.398(2) . ?
C5A H5A 0.9500 . ?
C3A C2A 1.382(2) . ?
C3A C4A 1.399(2) . ?
C3A H3A 0.9500 . ?
C4A C7A 1.485(2) . ?
C6A C1A 1.406(2) . ?
C6A H6A 0.9500 . ?
C2A C1A 1.415(2) . ?
C2A H2A 0.9500 . ?
C1A N1A 1.380(2) . ?
C7A O2A 1.2603(19) . ?
C7A O1A 1.2770(18) . ?
C9A N1A 1.453(2) . ?
C9A H9A1 0.9800 . ?
C9A H9A2 0.9800 . ?
C9A H9A3 0.9800 . ?
C8A N1A 1.448(2) . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
O1A Li1 1.889(3) . ?
O2A Li2 1.878(3) . ?
O1 Li2 1.966(3) 2 ?
O1 Li1 2.030(3) . ?
O1 H11 0.86(3) . ?
O1 H12 0.93(4) . ?
O2 Li1 1.971(3) . ?
O2 H21 0.86(3) . ?
O2 H22 0.83(3) . ?
Li1 O1B 1.921(3) . ?
Li1 Li2 3.509(4) 2 ?
Li1 H11 2.19(3) . ?
C4B C5B 1.388(2) . ?
C4B C3B 1.391(2) . ?
C4B C7B 1.506(2) . ?
C5B C6B 1.379(2) . ?
C5B H5B 0.9500 . ?
C7B O1B 1.2382(19) . ?
C7B O2B 1.2815(18) . ?
C7B Li2 2.764(3) 1_665 ?
C6B C1B 1.382(2) . ?
C6B N2B 1.467(2) . ?
C2B C3B 1.381(2) . ?
C2B C1B 1.382(2) . ?
C2B N1B 1.465(2) . ?
C1B H1B 0.9500 . ?
C3B H3B 0.9500 . ?
O2B Li2 1.972(3) 1_665 ?
O3 Li2 1.892(3) . ?
O3 H32 0.93(4) . ?
O3 H31 0.86(3) . ?
N2B O22B 1.219(2) . ?
N2B O21B 1.225(2) . ?
N1B O11B 1.223(2) . ?
N1B O12B 1.231(2) . ?
Li2 O1 1.966(3) 2_545 ?
Li2 O2B 1.972(3) 1_445 ?
Li2 C7B 2.764(3) 1_445 ?
Li2 Li1 3.509(4) 2_545 ?

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
C6A C5A C4A 121.42(15) . . ?
C6A C5A H5A 119.3 . . ?
C4A C5A H5A 119.3 . . ?
C2A C3A C4A 121.26(14) . . ?
C2A C3A H3A 119.4 . . ?
C4A C3A H3A 119.4 . . ?
C5A C4A C3A 117.99(14) . . ?
C5A C4A C7A 120.35(14) . . ?
C3A C4A C7A 121.60(13) . . ?
C5A C6A C1A 120.80(14) . . ?
C5A C6A H6A 119.6 . . ?
C1A C6A H6A 119.6 . . ?
C3A C2A C1A 120.85(15) . . ?
C3A C2A H2A 119.6 . . ?
C1A C2A H2A 119.6 . . ?
N1A C1A C6A 121.11(14) . . ?
N1A C1A C2A 121.20(15) . . ?
C6A C1A C2A 117.67(14) . . ?
O2A C7A O1A 121.39(14) . . ?
O2A C7A C4A 119.26(13) . . ?
O1A C7A C4A 119.34(14) . . ?
N1A C9A H9A1 109.5 . . ?
N1A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
N1A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
N1A C8A H8A1 109.5 . . ?
N1A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
N1A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C1A N1A C8A 120.19(14) . . ?
C1A N1A C9A 119.58(15) . . ?
C8A N1A C9A 116.01(15) . . ?
C7A O1A Li1 141.49(14) . . ?
C7A O2A Li2 146.71(15) . . ?
Li2 O1 Li1 122.86(13) 2 . ?
Li2 O1 H11 107.4(19) 2 . ?
Li1 O1 H11 88.8(18) . . ?
Li2 O1 H12 109(2) 2 . ?
Li1 O1 H12 121(2) . . ?
H11 O1 H12 101(3) . . ?
Li1 O2 H21 120.1(18) . . ?
Li1 O2 H22 116(2) . . ?
H21 O2 H22 105(2) . . ?
O1A Li1 O1B 123.14(16) . . ?
O1A Li1 O2 108.84(14) . . ?
O1B Li1 O2 107.04(16) . . ?
O1A Li1 O1 108.79(15) . . ?
O1B Li1 O1 93.76(13) . . ?
O2 Li1 O1 114.94(15) . . ?
O1A Li1 Li2 107.05(13) . 2 ?
O1B Li1 Li2 115.30(13) . 2 ?
O2 Li1 Li2 90.40(11) . 2 ?
O1 Li1 Li2 28.07(7) . 2 ?
O1A Li1 H11 130.1(9) . . ?
O1B Li1 H11 74.1(8) . . ?
O2 Li1 H11 108.6(8) . . ?
O1 Li1 H11 23.2(8) . . ?
Li2 Li1 H11 41.6(8) 2 . ?
C5B C4B C3B 120.10(14) . . ?
C5B C4B C7B 117.96(14) . . ?
C3B C4B C7B 121.91(13) . . ?
C6B C5B C4B 119.07(14) . . ?
C6B C5B H5B 120.5 . . ?
C4B C5B H5B 120.5 . . ?
O1B C7B O2B 124.85(14) . . ?
O1B C7B C4B 117.28(13) . . ?
O2B C7B C4B 117.88(14) . . ?
O1B C7B Li2 116.72(12) . 1_665 ?
O2B C7B Li2 40.42(9) . 1_665 ?
C4B C7B Li2 109.84(12) . 1_665 ?
C5B C6B C1B 122.68(14) . . ?
C5B C6B N2B 118.91(14) . . ?
C1B C6B N2B 118.38(14) . . ?
C3B C2B C1B 123.16(15) . . ?
C3B C2B N1B 118.83(14) . . ?
C1B C2B N1B 117.99(15) . . ?
C2B C1B C6B 116.55(15) . . ?
C2B C1B H1B 121.7 . . ?
C6B C1B H1B 121.7 . . ?
C2B C3B C4B 118.43(14) . . ?
C2B C3B H3B 120.8 . . ?
C4B C3B H3B 120.8 . . ?
C7B O2B Li2 114.66(13) . 1_665 ?
C7B O1B Li1 129.01(13) . . ?
Li2 O3 H32 120(2) . . ?
Li2 O3 H31 130(2) . . ?
H32 O3 H31 107(3) . . ?
O22B N2B O21B 124.42(15) . . ?
O22B N2B C6B 117.86(15) . . ?
O21B N2B C6B 117.72(14) . . ?
O11B N1B O12B 123.97(15) . . ?
O11B N1B C2B 117.99(15) . . ?
O12B N1B C2B 118.05(15) . . ?
O2A Li2 O3 108.99(16) . . ?
O2A Li2 O1 103.12(14) . 2_545 ?
O3 Li2 O1 105.00(15) . 2_545 ?
O2A Li2 O2B 127.59(16) . 1_445 ?
O3 Li2 O2B 104.72(14) . 1_445 ?
O1 Li2 O2B 105.45(15) 2_545 1_445 ?
O2A Li2 C7B 125.27(14) . 1_445 ?
O3 Li2 C7B 83.99(11) . 1_445 ?
O1 Li2 C7B 125.10(14) 2_545 1_445 ?
O2B Li2 C7B 24.92(6) 1_445 1_445 ?
O2A Li2 Li1 79.76(11) . 2_545 ?
O3 Li2 Li1 129.68(14) . 2_545 ?
O1 Li2 Li1 29.07(7) 2_545 2_545 ?
O2B Li2 Li1 107.46(12) 1_445 2_545 ?
C7B Li2 Li1 132.28(12) 1_445 2_545 ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        29.31
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.066


