#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:19:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180387 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/56/7205640.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7205640
loop_
_publ_author_name
'Wahl, Helene'
'Haynes, Delia A.'
'le Roex, Tanya'
_publ_section_title
;
 Solvate formation in lutidinium pamoate salts: a systematic study
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              2227
_journal_paper_doi               10.1039/c0ce00528b
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C23 H15 O6 1- , C7 H10 N 1+ , C3 H7 N O'
_chemical_formula_sum            'C33 H32 N2 O7'
_chemical_formula_weight         568.61
_chemical_name_common            '3,4 lutidinium pamoate DMF solvate'
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.507(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.794(3)
_cell_length_b                   13.334(3)
_cell_length_c                   16.615(3)
_cell_measurement_reflns_used    3156
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.433
_cell_measurement_theta_min      2.195
_cell_volume                     2862.3(10)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17002
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.04
_diffrn_reflns_theta_min         1.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.9685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         6269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0753P)²+0.6499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1589
_reflns_number_gt                4043
_reflns_number_total             6269
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00528b.txt
_cod_data_source_block           4
_cod_original_cell_volume        2862.4(9)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7205640
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.07715(15) 0.48009(15) 0.40627(13) 0.0509(5) Uani 1 1 d . . .
C5 C 0.1443(3) 0.3948(3) 0.4170(3) 0.0983(12) Uani 1 1 d . A .
H5A H 0.1356 0.3660 0.3606 0.147 Uiso 1 1 calc R . .
H5B H 0.1268 0.3443 0.4525 0.147 Uiso 1 1 calc R . .
H5C H 0.2164 0.4160 0.4451 0.147 Uiso 1 1 calc R . .
C2 C 0.0922(5) 0.5635(4) 0.4681(5) 0.0590(16) Uani 0.547(8) 1 d P A 1
H2 H 0.1578 0.5677 0.5128 0.071 Uiso 0.547(8) 1 calc PR A 1
O3 O 0.0296(3) 0.6263(2) 0.4674(2) 0.0540(14) Uani 0.547(8) 1 d P A 1
C4 C -0.0179(7) 0.4758(7) 0.3383(5) 0.063(2) Uani 0.547(8) 1 d P A 1
H4A H -0.0573 0.4177 0.3459 0.095 Uiso 0.547(8) 1 calc PR A 1
H4B H -0.0057 0.4694 0.2839 0.095 Uiso 0.547(8) 1 calc PR A 1
H4C H -0.0571 0.5372 0.3375 0.095 Uiso 0.547(8) 1 calc PR A 1
C2A C 0.1250(6) 0.5600(4) 0.4335(5) 0.0472(17) Uani 0.453(8) 1 d P A 2
H2A H 0.1980 0.5603 0.4481 0.057 Uiso 0.453(8) 1 calc PR A 2
O3A O 0.0836(4) 0.6366(3) 0.4422(3) 0.0584(16) Uani 0.453(8) 1 d P A 2
C4A C -0.0354(8) 0.4687(8) 0.3729(7) 0.063(3) Uani 0.453(8) 1 d P A 2
H4A1 H -0.0680 0.5351 0.3621 0.095 Uiso 0.453(8) 1 calc PR A 2
H4A2 H -0.0575 0.4329 0.4150 0.095 Uiso 0.453(8) 1 calc PR A 2
H4A3 H -0.0563 0.4305 0.3191 0.095 Uiso 0.453(8) 1 calc PR A 2
O211 O 0.44059(10) 0.67474(9) 0.40290(8) 0.0302(3) Uani 1 1 d . . .
H211 H 0.379(2) 0.6880(18) 0.4155(15) 0.056(7) Uiso 1 1 d . . .
C211 C 0.42690(13) 0.73712(13) 0.33524(11) 0.0237(4) Uani 1 1 d . . .
C212 C 0.33470(13) 0.79556(13) 0.30276(12) 0.0249(4) Uani 1 1 d . . .
C213 C 0.32127(14) 0.85869(13) 0.23477(12) 0.0260(4) Uani 1 1 d . . .
H213 H 0.2614 0.8999 0.2150 0.031 Uiso 1 1 calc R . .
C214 C 0.39477(13) 0.86373(13) 0.19344(12) 0.0243(4) Uani 1 1 d . . .
C215 C 0.37801(15) 0.92519(14) 0.12034(12) 0.0301(4) Uani 1 1 d . . .
H215 H 0.3185 0.9670 0.1011 0.036 Uiso 1 1 calc R . .
C216 C 0.44559(16) 0.92557(14) 0.07695(13) 0.0338(5) Uani 1 1 d . . .
H216 H 0.4334 0.9671 0.0279 0.041 Uiso 1 1 calc R . .
C217 C 0.53409(15) 0.86332(14) 0.10585(12) 0.0315(4) Uani 1 1 d . . .
H217 H 0.5803 0.8621 0.0748 0.038 Uiso 1 1 calc R . .
C218 C 0.55461(14) 0.80491(13) 0.17748(12) 0.0262(4) Uani 1 1 d . . .
H218 H 0.6154 0.7649 0.1960 0.031 Uiso 1 1 calc R . .
C219 C 0.48585(13) 0.80319(12) 0.22494(11) 0.0220(4) Uani 1 1 d . . .
C220 C 0.50388(13) 0.74285(12) 0.29932(11) 0.0219(4) Uani 1 1 d . . .
O221 O 0.26681(11) 0.73289(11) 0.40652(9) 0.0415(4) Uani 1 1 d . . .
C221 C 0.25184(14) 0.78751(14) 0.34211(13) 0.0299(4) Uani 1 1 d . . .
O222 O 0.17003(10) 0.83767(10) 0.30522(9) 0.0344(3) Uani 1 1 d . . .
C222 C 0.60353(12) 0.68330(13) 0.33880(11) 0.0235(4) Uani 1 1 d . . .
H22A H 0.6115 0.6380 0.2943 0.028 Uiso 1 1 calc R . .
H22B H 0.5967 0.6408 0.3854 0.028 Uiso 1 1 calc R . .
C223 C 0.70167(13) 0.74599(12) 0.37532(11) 0.0223(4) Uani 1 1 d . . .
O224 O 0.76712(10) 0.67199(9) 0.27489(8) 0.0289(3) Uani 1 1 d . . .
H224 H 0.831(2) 0.681(2) 0.2612(17) 0.073(8) Uiso 1 1 d . . .
C224 C 0.77921(13) 0.73804(12) 0.34051(11) 0.0229(4) Uani 1 1 d . . .
C225 C 0.87084(13) 0.79783(13) 0.37152(11) 0.0244(4) Uani 1 1 d . . .
C226 C 0.88286(13) 0.86345(13) 0.43784(12) 0.0248(4) Uani 1 1 d . . .
H226 H 0.9428 0.9046 0.4572 0.030 Uiso 1 1 calc R . .
C227 C 0.80863(13) 0.87152(12) 0.47823(11) 0.0230(4) Uani 1 1 d . . .
C228 C 0.82393(14) 0.93634(13) 0.54929(12) 0.0276(4) Uani 1 1 d . . .
H228 H 0.8844 0.9768 0.5692 0.033 Uiso 1 1 calc R . .
C229 C 0.75310(15) 0.94149(14) 0.58962(12) 0.0297(4) Uani 1 1 d . . .
H229 H 0.7642 0.9850 0.6373 0.036 Uiso 1 1 calc R . .
C230 C 0.66321(15) 0.88145(14) 0.55978(12) 0.0295(4) Uani 1 1 d . . .
H230 H 0.6142 0.8847 0.5881 0.035 Uiso 1 1 calc R . .
C231 C 0.64520(14) 0.81863(13) 0.49080(11) 0.0261(4) Uani 1 1 d . . .
H231 H 0.5838 0.7794 0.4719 0.031 Uiso 1 1 calc R . .
C232 C 0.71730(13) 0.81122(12) 0.44677(11) 0.0218(4) Uani 1 1 d . . .
O233 O 0.93908(10) 0.73594(11) 0.26751(9) 0.0402(4) Uani 1 1 d . . .
C233 C 0.95179(14) 0.78994(14) 0.33108(13) 0.0307(4) Uani 1 1 d . . .
O234 O 1.03361(10) 0.84423(10) 0.36743(9) 0.0365(4) Uani 1 1 d . . .
H234 H 1.096(3) 0.833(3) 0.338(2) 0.107(11) Uiso 1 1 d . . .
N11 N 0.12009(17) 0.78287(16) 0.57718(13) 0.0548(5) Uani 1 1 d . . .
C16 C 0.0890(5) 0.8131(4) 0.6388(3) 0.0372(12) Uani 0.518(4) 1 d P B 3
H16 H 0.0289 0.7854 0.6457 0.045 Uiso 0.518(4) 1 calc PR B 3
C15 C 0.1456(5) 0.8862(4) 0.6936(3) 0.0436(16) Uani 0.518(4) 1 d P B 3
H15 H 0.1240 0.9138 0.7373 0.052 Uiso 0.518(4) 1 calc PR B 3
C14 C 0.2392(12) 0.9191(10) 0.6818(8) 0.055(5) Uani 0.518(4) 1 d P B 3
C13 C 0.2679(7) 0.8782(7) 0.6172(6) 0.048(3) Uani 0.518(4) 1 d P B 3
C12 C 0.2016(7) 0.8063(7) 0.5659(5) 0.0238(14) Uani 0.518(4) 1 d P B 3
H12 H 0.2190 0.7745 0.5216 0.029 Uiso 0.518(4) 1 calc PR B 3
C17 C 0.3640(3) 0.9112(3) 0.6077(3) 0.0490(14) Uani 0.518(4) 1 d P B 3
H17A H 0.4225 0.8937 0.6595 0.074 Uiso 0.518(4) 1 calc PR B 3
H17B H 0.3620 0.9840 0.5993 0.074 Uiso 0.518(4) 1 calc PR B 3
H17C H 0.3721 0.8780 0.5578 0.074 Uiso 0.518(4) 1 calc PR B 3
C18 C 0.3038(5) 0.9978(3) 0.7432(3) 0.0553(16) Uani 0.518(4) 1 d P B 3
H18A H 0.3134 1.0557 0.7105 0.083 Uiso 0.518(4) 1 calc PR B 3
H18B H 0.3715 0.9694 0.7767 0.083 Uiso 0.518(4) 1 calc PR B 3
H18C H 0.2684 1.0191 0.7822 0.083 Uiso 0.518(4) 1 calc PR B 3
C18A C 0.3897(4) 0.9707(4) 0.6808(3) 0.0519(15) Uani 0.482(4) 1 d P B 4
H18D H 0.3703 1.0417 0.6739 0.078 Uiso 0.482(4) 1 calc PR B 4
H18E H 0.4364 0.9560 0.6494 0.078 Uiso 0.482(4) 1 calc PR B 4
H18F H 0.4247 0.9558 0.7419 0.078 Uiso 0.482(4) 1 calc PR B 4
C15A C 0.2771(6) 0.8465(5) 0.5736(4) 0.054(2) Uani 0.482(4) 1 d P B 4
H15A H 0.3292 0.8456 0.5484 0.064 Uiso 0.482(4) 1 calc PR B 4
C14A C 0.2935(7) 0.9067(7) 0.6456(7) 0.0366(18) Uani 0.482(4) 1 d P B 4
C17A C 0.2315(5) 0.9736(4) 0.7625(3) 0.0601(17) Uani 0.482(4) 1 d P B 4
H17D H 0.1723 0.9621 0.7810 0.090 Uiso 0.482(4) 1 calc PR B 4
H17E H 0.2339 1.0445 0.7479 0.090 Uiso 0.482(4) 1 calc PR B 4
H17F H 0.2955 0.9555 0.8091 0.090 Uiso 0.482(4) 1 calc PR B 4
C12A C 0.1323(6) 0.8529(6) 0.6511(5) 0.0528(18) Uani 0.482(4) 1 d P B 4
H12A H 0.0787 0.8575 0.6746 0.063 Uiso 0.482(4) 1 calc PR B 4
C13A C 0.2202(10) 0.9104(11) 0.6853(9) 0.040(4) Uani 0.482(4) 1 d P B 4
C16A C 0.1977(10) 0.7928(8) 0.5395(5) 0.034(2) Uani 0.482(4) 1 d P B 4
H16A H 0.1896 0.7583 0.4875 0.041 Uiso 0.482(4) 1 calc PR B 4
H11 H 0.0728 0.7271 0.5384 0.124(13) Uiso 1 1 d R . .
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'
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
C2A N1 C5 113.2(4) . . ?
C4 N1 C5 116.6(5) . . ?
C2A N1 C4A 125.5(6) . . ?
C5 N1 C4A 121.2(5) . . ?
C4 N1 C2 117.1(5) . . ?
C5 N1 C2 125.5(3) . . ?
O3 C2 N1 126.4(5) . . ?
O3A C2A N1 123.6(6) . . ?
O211 C211 C220 118.92(16) . . ?
O211 C211 C212 119.67(15) . . ?
C220 C211 C212 121.41(16) . . ?
C213 C212 C211 119.56(16) . . ?
C213 C212 C221 119.89(17) . . ?
C211 C212 C221 120.54(16) . . ?
C212 C213 C214 121.23(17) . . ?
C213 C214 C215 121.06(16) . . ?
C213 C214 C219 118.94(16) . . ?
C215 C214 C219 119.97(16) . . ?
C216 C215 C214 121.29(17) . . ?
C215 C216 C217 119.15(18) . . ?
C218 C217 C216 121.41(17) . . ?
C217 C218 C219 120.95(17) . . ?
C220 C219 C214 120.11(15) . . ?
C220 C219 C218 122.71(16) . . ?
C214 C219 C218 117.16(16) . . ?
C211 C220 C219 118.48(16) . . ?
C211 C220 C222 119.75(15) . . ?
C219 C220 C222 121.75(14) . . ?
O221 C221 O222 124.92(17) . . ?
O221 C221 C212 119.35(17) . . ?
O222 C221 C212 115.73(17) . . ?
C220 C222 C223 115.29(14) . . ?
C224 C223 C232 118.70(15) . . ?
C224 C223 C222 119.95(15) . . ?
C232 C223 C222 121.33(15) . . ?
O224 C224 C223 119.07(15) . . ?
O224 C224 C225 119.53(15) . . ?
C223 C224 C225 121.39(16) . . ?
C226 C225 C224 119.24(16) . . ?
C226 C225 C233 120.47(16) . . ?
C224 C225 C233 120.28(16) . . ?
C225 C226 C227 121.82(16) . . ?
C226 C227 C228 121.41(16) . . ?
C226 C227 C232 118.44(16) . . ?
C228 C227 C232 120.14(16) . . ?
C229 C228 C227 121.03(17) . . ?
C228 C229 C230 119.35(17) . . ?
C231 C230 C229 121.33(17) . . ?
C230 C231 C232 121.03(17) . . ?
C223 C232 C231 122.61(16) . . ?
C223 C232 C227 120.27(15) . . ?
C231 C232 C227 117.11(16) . . ?
O233 C233 O234 124.13(17) . . ?
O233 C233 C225 121.27(16) . . ?
O234 C233 C225 114.59(16) . . ?
C12 N11 C16 127.1(4) . . ?
C12 N11 C16A 18.3(5) . . ?
C16 N11 C16A 145.2(5) . . ?
C12 N11 C12A 96.8(5) . . ?
C16 N11 C12A 30.8(3) . . ?
C16A N11 C12A 114.6(5) . . ?
N11 C16 C15 118.2(5) . . ?
C16 C15 C14 117.0(6) . . ?
C13 C14 C15 120.1(9) . . ?
C13 C14 C18 122.4(14) . . ?
C15 C14 C18 117.5(11) . . ?
C14 C13 C12 116.3(10) . . ?
C14 C13 C17 119.0(11) . . ?
C12 C13 C17 124.7(9) . . ?
N11 C12 C13 121.1(7) . . ?
C16A C15A C14A 124.5(8) . . ?
C13A C14A C15A 120.2(10) . . ?
C13A C14A C18A 118.9(10) . . ?
C15A C14A C18A 120.9(8) . . ?
C13A C12A N11 120.8(8) . . ?
C12A C13A C14A 117.9(11) . . ?
C12A C13A C17A 118.6(10) . . ?
C14A C13A C17A 123.5(12) . . ?
C15A C16A N11 121.5(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2A 1.252(6) . ?
N1 C4 1.400(9) . ?
N1 C5 1.438(3) . ?
N1 C4A 1.462(10) . ?
N1 C2 1.478(7) . ?
C2 O3 1.199(6) . ?
C2A O3A 1.203(8) . ?
O211 C211 1.357(2) . ?
C211 C220 1.391(2) . ?
C211 C212 1.427(2) . ?
C212 C213 1.368(3) . ?
C212 C221 1.506(2) . ?
C213 C214 1.411(2) . ?
C214 C215 1.415(3) . ?
C214 C219 1.429(2) . ?
C215 C216 1.364(3) . ?
C216 C217 1.414(3) . ?
C217 C218 1.366(3) . ?
C218 C219 1.430(2) . ?
C219 C220 1.422(2) . ?
C220 C222 1.523(2) . ?
O221 C221 1.250(2) . ?
C221 O222 1.270(2) . ?
C222 C223 1.525(2) . ?
C223 C224 1.387(2) . ?
C223 C232 1.426(2) . ?
O224 C224 1.366(2) . ?
C224 C225 1.429(2) . ?
C225 C226 1.371(2) . ?
C225 C233 1.495(2) . ?
C226 C227 1.411(2) . ?
C227 C228 1.418(2) . ?
C227 C232 1.430(2) . ?
C228 C229 1.366(2) . ?
C229 C230 1.412(3) . ?
C230 C231 1.370(2) . ?
C231 C232 1.430(2) . ?
O233 C233 1.239(2) . ?
C233 O234 1.298(2) . ?
N11 C12 1.242(9) . ?
N11 C16 1.305(6) . ?
N11 C16A 1.423(12) . ?
N11 C12A 1.505(9) . ?
C16 C15 1.375(7) . ?
C15 C14 1.440(18) . ?
C14 C13 1.379(16) . ?
C14 C18 1.517(12) . ?
C13 C12 1.392(12) . ?
C13 C17 1.457(11) . ?
C18A C14A 1.512(9) . ?
C15A C16A 1.265(14) . ?
C15A C14A 1.393(11) . ?
C14A C13A 1.387(16) . ?
C17A C13A 1.497(13) . ?
C12A C13A 1.377(18) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 O3 1.05 1.75 2.766(4) 162.0 .
N11 H11 O3A 1.05 2.05 2.880(5) 134.2 .
