#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:19:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180387 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/56/7205639.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_7205639
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            '2,4 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                 108.7730(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9767(12)
_cell_length_b                   12.6966(11)
_cell_length_c                   16.7676(15)
_cell_measurement_reflns_used    3918
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.524
_cell_measurement_theta_min      2.223
_cell_volume                     2817.2(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.912
_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  0.0663
_diffrn_reflns_av_sigmaI/netI    0.0634
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16490
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.54
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         6121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0622P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                4032
_reflns_number_total             6121
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00528b.txt
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7205639
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
N11 N 0.24529(11) 0.66792(11) 0.56393(9) 0.0252(3) Uani 1 1 d . . .
H11 H 0.2543(15) 0.6978(16) 0.5133(13) 0.055(6) Uiso 1 1 d . . .
C12 C 0.31804(13) 0.60577(13) 0.61466(10) 0.0258(4) Uani 1 1 d . . .
C13 C 0.30187(13) 0.56226(14) 0.68444(10) 0.0285(4) Uani 1 1 d . . .
H13 H 0.3522 0.5182 0.7207 0.034 Uiso 1 1 calc R . .
C14 C 0.21375(14) 0.58135(14) 0.70277(10) 0.0294(4) Uani 1 1 d . . .
C15 C 0.14086(13) 0.64621(14) 0.64831(10) 0.0280(4) Uani 1 1 d . . .
H15 H 0.0794 0.6607 0.6590 0.034 Uiso 1 1 calc R . .
C16 C 0.15884(13) 0.68864(14) 0.57948(10) 0.0272(4) Uani 1 1 d . . .
H16 H 0.1097 0.7331 0.5424 0.033 Uiso 1 1 calc R . .
C17 C 0.41140(13) 0.58901(15) 0.59137(12) 0.0365(5) Uani 1 1 d . . .
H17A H 0.3942 0.5508 0.5378 0.055 Uiso 1 1 calc R . .
H17B H 0.4602 0.5478 0.6355 0.055 Uiso 1 1 calc R . .
H17C H 0.4411 0.6574 0.5856 0.055 Uiso 1 1 calc R . .
C18 C 0.19683(17) 0.53427(17) 0.77929(11) 0.0447(5) Uani 1 1 d . . .
H18A H 0.1412 0.5711 0.7909 0.067 Uiso 1 1 calc R . .
H18B H 0.2585 0.5414 0.8277 0.067 Uiso 1 1 calc R . .
H18C H 0.1798 0.4595 0.7691 0.067 Uiso 1 1 calc R . .
O211 O 0.45914(9) 0.81555(9) 0.41665(7) 0.0226(3) Uani 1 1 d . . .
H211 H 0.4091(18) 0.8049(18) 0.4359(14) 0.068(8) Uiso 1 1 d . . .
O221 O 0.29111(8) 0.74587(9) 0.42731(7) 0.0252(3) Uani 1 1 d . . .
O222 O 0.18038(8) 0.67857(9) 0.31074(7) 0.0238(3) Uani 1 1 d . . .
O224 O 0.77325(9) 0.81871(9) 0.27604(7) 0.0230(3) Uani 1 1 d . . .
H224 H 0.8272(17) 0.8103(17) 0.2592(13) 0.059(7) Uiso 1 1 d . . .
O233 O 0.94698(8) 0.76213(9) 0.27050(7) 0.0269(3) Uani 1 1 d . . .
O234 O 1.04659(8) 0.66409(9) 0.37538(7) 0.0253(3) Uani 1 1 d . . .
H234 H 1.1086(17) 0.6770(19) 0.3460(13) 0.081(8) Uiso 1 1 d . . .
C211 C 0.44257(11) 0.75513(12) 0.34636(9) 0.0173(3) Uani 1 1 d . . .
C212 C 0.34764(11) 0.70264(12) 0.31170(9) 0.0180(3) Uani 1 1 d . . .
C213 C 0.32979(12) 0.64557(12) 0.23921(9) 0.0191(3) Uani 1 1 d . . .
H213 H 0.2666 0.6109 0.2162 0.023 Uiso 1 1 calc R . .
C214 C 0.40257(11) 0.63680(12) 0.19780(9) 0.0181(3) Uani 1 1 d . . .
C215 C 0.38167(12) 0.58083(13) 0.12140(10) 0.0216(4) Uani 1 1 d . . .
H215 H 0.3179 0.5474 0.0981 0.026 Uiso 1 1 calc R . .
C216 C 0.45147(12) 0.57382(13) 0.08041(10) 0.0222(4) Uani 1 1 d . . .
H216 H 0.4367 0.5353 0.0293 0.027 Uiso 1 1 calc R . .
C217 C 0.54589(12) 0.62435(12) 0.11479(9) 0.0206(4) Uani 1 1 d . . .
H217 H 0.5946 0.6195 0.0864 0.025 Uiso 1 1 calc R . .
C218 C 0.56839(12) 0.68016(12) 0.18829(9) 0.0185(3) Uani 1 1 d . . .
H218 H 0.6322 0.7139 0.2098 0.022 Uiso 1 1 calc R . .
C219 C 0.49790(11) 0.68857(12) 0.23325(9) 0.0166(3) Uani 1 1 d . . .
C220 C 0.51747(11) 0.74790(12) 0.30898(9) 0.0170(3) Uani 1 1 d . . .
C221 C 0.26804(12) 0.71010(12) 0.35352(10) 0.0192(3) Uani 1 1 d . . .
C222 C 0.61583(11) 0.80917(12) 0.34592(9) 0.0185(3) Uani 1 1 d . . .
H22A H 0.6239 0.8566 0.3016 0.022 Uiso 1 1 calc R . .
H22B H 0.6090 0.8542 0.3920 0.022 Uiso 1 1 calc R . .
C223 C 0.71233(11) 0.74479(12) 0.38032(9) 0.0174(3) Uani 1 1 d . . .
C224 C 0.78774(12) 0.75349(12) 0.34334(9) 0.0181(3) Uani 1 1 d . . .
C225 C 0.88078(11) 0.69677(12) 0.37568(9) 0.0183(3) Uani 1 1 d . . .
C226 C 0.89557(11) 0.63236(12) 0.44409(9) 0.0191(3) Uani 1 1 d . . .
H226 H 0.9563 0.5928 0.4641 0.023 Uiso 1 1 calc R . .
C227 C 0.82276(11) 0.62340(12) 0.48559(9) 0.0179(3) Uani 1 1 d . . .
C228 C 0.84171(12) 0.56261(13) 0.55996(10) 0.0214(4) Uani 1 1 d . . .
H228 H 0.9021 0.5224 0.5797 0.026 Uiso 1 1 calc R . .
C229 C 0.77430(12) 0.56086(13) 0.60386(10) 0.0232(4) Uani 1 1 d . . .
H229 H 0.7880 0.5203 0.6539 0.028 Uiso 1 1 calc R . .
C230 C 0.68431(12) 0.61999(13) 0.57389(9) 0.0220(4) Uani 1 1 d . . .
H230 H 0.6381 0.6200 0.6048 0.026 Uiso 1 1 calc R . .
C231 C 0.66231(12) 0.67735(12) 0.50112(9) 0.0199(4) Uani 1 1 d . . .
H231 H 0.6004 0.7150 0.4818 0.024 Uiso 1 1 calc R . .
C232 C 0.73064(11) 0.68172(12) 0.45383(9) 0.0174(3) Uani 1 1 d . . .
C233 C 0.96152(12) 0.71010(13) 0.33582(10) 0.0201(4) Uani 1 1 d . . .
C1 C 1.03479(15) 0.55096(18) 0.16239(12) 0.0463(5) Uani 1 1 d . A .
H1A H 1.0777 0.4881 0.1728 0.069 Uiso 1 1 calc R . .
H1B H 1.0162 0.5669 0.2127 0.069 Uiso 1 1 calc R . .
H1C H 1.0717 0.6107 0.1495 0.069 Uiso 1 1 calc R . .
N2 N 0.94439(11) 0.53195(11) 0.09192(8) 0.0259(3) Uani 1 1 d . . .
C3 C 0.87270(17) 0.61664(17) 0.06387(14) 0.0500(6) Uani 1 1 d . A .
H3A H 0.8982 0.6675 0.0316 0.075 Uiso 1 1 calc R . .
H3B H 0.8632 0.6518 0.1128 0.075 Uiso 1 1 calc R . .
H3C H 0.8079 0.5882 0.0281 0.075 Uiso 1 1 calc R . .
C4A C 0.9360(4) 0.4405(4) 0.0503(3) 0.0275(10) Uani 0.777(6) 1 d P A 1
H4A H 0.9885 0.3905 0.0718 0.033 Uiso 0.777(6) 1 calc PR A 1
O5A O 0.86704(14) 0.41560(15) -0.01259(12) 0.0432(8) Uani 0.777(6) 1 d P A 1
C4B C 0.9089(18) 0.453(2) 0.0396(18) 0.070(10) Uiso 0.223(6) 1 d P A 2
H4B H 0.8452 0.4597 -0.0031 0.084 Uiso 0.223(6) 1 calc PR A 2
O5B O 0.9577(5) 0.3718(6) 0.0456(4) 0.048(3) Uani 0.223(6) 1 d P A 2
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
C16 N11 C12 122.33(15) . . ?
N11 C12 C13 118.27(16) . . ?
N11 C12 C17 117.57(15) . . ?
C13 C12 C17 124.16(17) . . ?
C12 C13 C14 121.32(17) . . ?
C13 C14 C15 118.18(16) . . ?
C13 C14 C18 121.09(17) . . ?
C15 C14 C18 120.73(17) . . ?
C16 C15 C14 119.36(17) . . ?
N11 C16 C15 120.54(17) . . ?
O211 C211 C220 119.08(14) . . ?
O211 C211 C212 119.41(13) . . ?
C220 C211 C212 121.50(14) . . ?
C213 C212 C211 119.21(14) . . ?
C213 C212 C221 119.97(14) . . ?
C211 C212 C221 120.82(14) . . ?
C212 C213 C214 121.74(15) . . ?
C213 C214 C215 121.07(14) . . ?
C213 C214 C219 118.82(14) . . ?
C215 C214 C219 120.08(14) . . ?
C216 C215 C214 121.15(15) . . ?
C215 C216 C217 119.34(15) . . ?
C218 C217 C216 121.10(14) . . ?
C217 C218 C219 121.22(14) . . ?
C218 C219 C220 122.97(14) . . ?
C218 C219 C214 117.10(14) . . ?
C220 C219 C214 119.91(13) . . ?
C211 C220 C219 118.81(14) . . ?
C211 C220 C222 119.71(13) . . ?
C219 C220 C222 121.36(13) . . ?
O221 C221 O222 124.38(14) . . ?
O221 C221 C212 119.31(14) . . ?
O222 C221 C212 116.31(13) . . ?
C223 C222 C220 116.89(13) . . ?
C224 C223 C232 118.76(14) . . ?
C224 C223 C222 119.67(14) . . ?
C232 C223 C222 121.39(13) . . ?
O224 C224 C223 119.13(14) . . ?
O224 C224 C225 119.64(13) . . ?
C223 C224 C225 121.21(14) . . ?
C226 C225 C224 119.44(14) . . ?
C226 C225 C233 120.67(14) . . ?
C224 C225 C233 119.88(14) . . ?
C225 C226 C227 121.55(14) . . ?
C226 C227 C228 121.20(14) . . ?
C226 C227 C232 118.71(14) . . ?
C228 C227 C232 120.01(14) . . ?
C229 C228 C227 121.04(15) . . ?
C228 C229 C230 119.23(15) . . ?
C231 C230 C229 121.30(14) . . ?
C230 C231 C232 121.22(15) . . ?
C223 C232 C231 122.56(14) . . ?
C223 C232 C227 120.20(13) . . ?
C231 C232 C227 117.17(14) . . ?
O233 C233 O234 123.65(14) . . ?
O233 C233 C225 121.55(14) . . ?
O234 C233 C225 114.80(14) . . ?
C4B N2 C3 106.0(10) . . ?
C4A N2 C3 122.7(3) . . ?
C4B N2 C1 135.6(10) . . ?
C4A N2 C1 118.5(3) . . ?
C3 N2 C1 118.36(16) . . ?
O5A C4A N2 126.0(5) . . ?
O5B C4B N2 120(2) . . ?
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
N11 C16 1.342(2) . ?
N11 C12 1.350(2) . ?
C12 C13 1.377(2) . ?
C12 C17 1.493(2) . ?
C13 C14 1.383(2) . ?
C14 C15 1.397(2) . ?
C14 C18 1.502(2) . ?
C15 C16 1.368(2) . ?
O211 C211 1.3623(18) . ?
O221 C221 1.2587(18) . ?
O222 C221 1.2689(18) . ?
O224 C224 1.3612(18) . ?
O233 C233 1.2387(18) . ?
O234 C233 1.2991(18) . ?
C211 C220 1.385(2) . ?
C211 C212 1.430(2) . ?
C212 C213 1.367(2) . ?
C212 C221 1.497(2) . ?
C213 C214 1.408(2) . ?
C214 C215 1.411(2) . ?
C214 C219 1.432(2) . ?
C215 C216 1.365(2) . ?
C216 C217 1.413(2) . ?
C217 C218 1.368(2) . ?
C218 C219 1.424(2) . ?
C219 C220 1.425(2) . ?
C220 C222 1.527(2) . ?
C222 C223 1.523(2) . ?
C223 C224 1.389(2) . ?
C223 C232 1.422(2) . ?
C224 C225 1.432(2) . ?
C225 C226 1.369(2) . ?
C225 C233 1.495(2) . ?
C226 C227 1.410(2) . ?
C227 C228 1.417(2) . ?
C227 C232 1.431(2) . ?
C228 C229 1.370(2) . ?
C229 C230 1.411(2) . ?
C230 C231 1.368(2) . ?
C231 C232 1.425(2) . ?
C1 N2 1.446(2) . ?
N2 C4B 1.32(3) . ?
N2 C4A 1.340(5) . ?
N2 C3 1.442(2) . ?
C4A O5A 1.219(5) . ?
C4B O5B 1.22(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 O221 0.97(2) 1.79(2) 2.7534(17) 171.0(18) .
O234 H234 O222 1.14(2) 1.32(2) 2.4514(15) 173(2) 1_655
