#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:19:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180387 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/56/7205642.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_7205642
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+ , C5 H9 N O'
_chemical_formula_sum            'C35 H34 N2 O7'
_chemical_formula_weight         594.64
_chemical_name_common            '2,3 lutidinium pamoate NMP 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                 112.929(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6610(19)
_cell_length_b                   13.7621(19)
_cell_length_c                   16.906(2)
_cell_measurement_reflns_used    3868
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.452
_cell_measurement_theta_min      2.207
_cell_volume                     2927.3(7)
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17075
_diffrn_reflns_theta_full        26.64
_diffrn_reflns_theta_max         26.64
_diffrn_reflns_theta_min         1.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.9759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         6102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0843P)²+1.6923P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1615
_refine_ls_wR_factor_ref         0.1812
_reflns_number_gt                4329
_reflns_number_total             6102
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00528b.txt
_cod_data_source_block           6
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7205642
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 0.1971(2) 1.10792(19) 0.18377(19) 0.0648(8) Uani 1 1 d . . .
H11 H 0.1961 1.0812 0.2307 0.078 Uiso 1 1 calc R . .
C12 C 0.2798(2) 1.08875(18) 0.16649(18) 0.0443(6) Uani 1 1 d . . .
C13 C 0.2870(2) 1.13074(18) 0.09205(16) 0.0434(6) Uani 1 1 d . . .
C14 C 0.2073(2) 1.18770(19) 0.0425(2) 0.0521(7) Uani 1 1 d . . .
H14 H 0.2102 1.2159 -0.0078 0.063 Uiso 1 1 calc R . .
C15 C 0.1198(3) 1.2065(2) 0.0638(3) 0.1003(18) Uani 1 1 d . . .
H15 H 0.0641 1.2479 0.0287 0.120 Uiso 1 1 calc R . .
C16 C 0.1151(3) 1.1620(3) 0.1400(3) 0.0706(10) Uani 1 1 d . . .
H16 H 0.0570 1.1714 0.1568 0.085 Uiso 1 1 calc R . .
C17 C 0.3637(2) 1.02461(18) 0.22247(19) 0.0512(7) Uani 1 1 d . . .
H17A H 0.3445 1.0009 0.2692 0.077 Uiso 1 1 calc R . .
H17B H 0.4308 1.0607 0.2466 0.077 Uiso 1 1 calc R . .
H17C H 0.3721 0.9693 0.1891 0.077 Uiso 1 1 calc R . .
C18 C 0.3792(2) 1.1102(2) 0.0705(2) 0.0594(8) Uani 1 1 d . . .
H18A H 0.3740 1.1484 0.0201 0.089 Uiso 1 1 calc R . .
H18B H 0.3807 1.0409 0.0578 0.089 Uiso 1 1 calc R . .
H18C H 0.4446 1.1277 0.1192 0.089 Uiso 1 1 calc R . .
O211 O 0.25327(12) 0.70344(11) 0.24613(9) 0.0279(3) Uani 1 1 d . . .
C211 C 0.23864(15) 0.76398(14) 0.17882(12) 0.0220(4) Uani 1 1 d . . .
H211 H 0.193(3) 0.718(2) 0.262(2) 0.069(10) Uiso 1 1 d . . .
C212 C 0.14505(15) 0.82298(14) 0.14539(13) 0.0225(4) Uani 1 1 d . . .
C213 C 0.12855(15) 0.88074(14) 0.07508(13) 0.0225(4) Uani 1 1 d . . .
H213 H 0.0672 0.9210 0.0538 0.027 Uiso 1 1 calc R . .
C214 C 0.20064(15) 0.88172(14) 0.03373(12) 0.0219(4) Uani 1 1 d . . .
C215 C 0.17844(16) 0.93533(15) -0.04298(13) 0.0250(4) Uani 1 1 d . . .
H215 H 0.1163 0.9744 -0.0650 0.030 Uiso 1 1 calc R . .
C216 C 0.24544(17) 0.93149(15) -0.08582(13) 0.0283(5) Uani 1 1 d . . .
H216 H 0.2292 0.9665 -0.1378 0.034 Uiso 1 1 calc R . .
C217 C 0.33880(17) 0.87490(16) -0.05176(13) 0.0281(5) Uani 1 1 d . . .
H217 H 0.3850 0.8719 -0.0816 0.034 Uiso 1 1 calc R . .
C218 C 0.36413(16) 0.82421(15) 0.02330(13) 0.0248(4) Uani 1 1 d . . .
H218 H 0.4286 0.7883 0.0455 0.030 Uiso 1 1 calc R . .
C219 C 0.29532(15) 0.82443(14) 0.06884(12) 0.0221(4) Uani 1 1 d . . .
C220 C 0.31541(15) 0.76724(14) 0.14391(13) 0.0221(4) Uani 1 1 d . . .
C221 C 0.06581(15) 0.82071(15) 0.18658(13) 0.0243(4) Uani 1 1 d . . .
O221 O 0.07990(11) 0.76751(11) 0.24946(9) 0.0291(3) Uani 1 1 d . . .
O222 O -0.01619(12) 0.87584(12) 0.15169(10) 0.0331(4) Uani 1 1 d . . .
H222 H -0.079(3) 0.872(3) 0.183(2) 0.097(13) Uiso 1 1 d . . .
C222 C 0.41632(15) 0.70665(15) 0.18371(13) 0.0241(4) Uani 1 1 d . . .
H22A H 0.4227 0.6641 0.1387 0.029 Uiso 1 1 calc R . .
H22B H 0.4093 0.6642 0.2285 0.029 Uiso 1 1 calc R . .
C223 C 0.51826(15) 0.76596(14) 0.22387(13) 0.0227(4) Uani 1 1 d . . .
C224 C 0.59516(15) 0.76120(14) 0.18956(13) 0.0237(4) Uani 1 1 d . . .
O224 O 0.58071(12) 0.69939(11) 0.12313(10) 0.0299(4) Uani 1 1 d . . .
H224 H 0.638(2) 0.707(2) 0.1097(19) 0.059(9) Uiso 1 1 d . . .
C225 C 0.68942(15) 0.81934(14) 0.22295(13) 0.0244(4) Uani 1 1 d . . .
C226 C 0.70594(16) 0.87835(15) 0.29218(14) 0.0274(5) Uani 1 1 d . . .
H226 H 0.7671 0.9188 0.3128 0.033 Uiso 1 1 calc R . .
C227 C 0.63399(16) 0.88043(15) 0.33361(13) 0.0264(5) Uani 1 1 d . . .
C228 C 0.65724(18) 0.93356(17) 0.41062(15) 0.0336(5) Uani 1 1 d . . .
H228 H 0.7198 0.9721 0.4325 0.040 Uiso 1 1 calc R . .
C229 C 0.59134(19) 0.93033(17) 0.45397(15) 0.0354(5) Uani 1 1 d . . .
H229 H 0.6084 0.9656 0.5060 0.043 Uiso 1 1 calc R . .
C230 C 0.49770(17) 0.87420(16) 0.42085(14) 0.0306(5) Uani 1 1 d . . .
H230 H 0.4518 0.8718 0.4510 0.037 Uiso 1 1 calc R . .
C231 C 0.47171(16) 0.82298(15) 0.34577(13) 0.0264(5) Uani 1 1 d . . .
H231 H 0.4075 0.7867 0.3243 0.032 Uiso 1 1 calc R . .
C232 C 0.53946(15) 0.82322(14) 0.29930(13) 0.0231(4) Uani 1 1 d . . .
C233 C 0.77132(17) 0.81370(16) 0.18434(15) 0.0295(5) Uani 1 1 d . . .
O233 O 0.76003(13) 0.75445(13) 0.12586(12) 0.0442(5) Uani 1 1 d . . .
O234 O 0.85090(12) 0.87114(11) 0.21625(10) 0.0336(4) Uani 1 1 d . . .
O1 O 0.2121(2) 0.9978(2) 0.3248(2) 0.0557(10) Uani 0.699(5) 1 d P A 1
C1 C 0.1336(4) 0.9990(3) 0.3438(3) 0.0366(11) Uani 0.699(5) 1 d P A 1
N2 N 0.1156(3) 0.9385(2) 0.4006(2) 0.0443(10) Uani 0.699(5) 1 d P A 1
C3 C 0.0148(6) 0.9519(5) 0.4072(5) 0.0468(16) Uani 0.699(5) 1 d P A 1
H3A H 0.0226 0.9515 0.4680 0.056 Uiso 0.699(5) 1 calc PR A 1
H3B H -0.0363 0.9006 0.3755 0.056 Uiso 0.699(5) 1 calc PR A 1
C4 C -0.0215(5) 1.0529(3) 0.3658(4) 0.0574(13) Uani 0.699(5) 1 d P A 1
H4A H -0.0993 1.0543 0.3323 0.069 Uiso 0.699(5) 1 calc PR A 1
H4B H -0.0025 1.1046 0.4100 0.069 Uiso 0.699(5) 1 calc PR A 1
C5 C 0.0390(4) 1.0655(4) 0.3073(4) 0.0374(11) Uani 0.699(5) 1 d P A 1
H5A H -0.0060 1.0469 0.2476 0.045 Uiso 0.699(5) 1 calc PR A 1
H5B H 0.0621 1.1337 0.3078 0.045 Uiso 0.699(5) 1 calc PR A 1
C6 C 0.1831(9) 0.8587(8) 0.4420(7) 0.086(5) Uani 0.699(5) 1 d P A 1
H6A H 0.1447 0.7975 0.4217 0.129 Uiso 0.699(5) 1 calc PR A 1
H6B H 0.2043 0.8639 0.5043 0.129 Uiso 0.699(5) 1 calc PR A 1
H6C H 0.2466 0.8599 0.4284 0.129 Uiso 0.699(5) 1 calc PR A 1
O1A O -0.0437(5) 0.9232(5) 0.4381(4) 0.052(2) Uani 0.301(5) 1 d P A 2
C1A C 0.0360(15) 0.9192(13) 0.4140(13) 0.056(5) Uani 0.301(5) 1 d P A 2
N2A N 0.0717(6) 0.9883(6) 0.3741(4) 0.0345(18) Uani 0.301(5) 1 d P A 2
C3A C 0.1672(9) 0.9675(8) 0.3724(8) 0.038(3) Uani 0.301(5) 1 d P A 2
H3C H 0.2186 1.0207 0.3984 0.046 Uiso 0.301(5) 1 calc PR A 2
H3D H 0.1614 0.9565 0.3129 0.046 Uiso 0.301(5) 1 calc PR A 2
C4A C 0.2026(13) 0.8692(19) 0.4289(11) 0.039(4) Uani 0.301(5) 1 d P A 2
H4D H 0.2147 0.8160 0.3944 0.046 Uiso 0.301(5) 1 calc PR A 2
H4C H 0.2689 0.8801 0.4801 0.046 Uiso 0.301(5) 1 calc PR A 2
C5A C 0.1165(9) 0.8454(10) 0.4542(11) 0.083(6) Uani 0.301(5) 1 d P A 2
H5C H 0.1402 0.8474 0.5175 0.100 Uiso 0.301(5) 1 calc PR A 2
H5D H 0.0885 0.7797 0.4337 0.100 Uiso 0.301(5) 1 calc PR A 2
C6A C 0.0097(12) 1.0718(10) 0.3306(9) 0.055(4) Uani 0.301(5) 1 d P A 2
H6E H 0.0575 1.1257 0.3324 0.082 Uiso 0.301(5) 1 calc PR A 2
H6D H -0.0373 1.0914 0.3591 0.082 Uiso 0.301(5) 1 calc PR A 2
H6F H -0.0331 1.0550 0.2706 0.082 Uiso 0.301(5) 1 calc PR 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
C12 N11 C16 128.0(3) . . ?
N11 C12 C13 118.8(3) . . ?
N11 C12 C17 120.5(3) . . ?
C13 C12 C17 120.6(3) . . ?
C14 C13 C12 118.1(3) . . ?
C14 C13 C18 121.7(3) . . ?
C12 C13 C18 120.2(3) . . ?
C13 C14 C15 121.0(3) . . ?
C14 C15 C16 119.2(3) . . ?
N11 C16 C15 114.7(3) . . ?
O211 C211 C220 119.05(17) . . ?
O211 C211 C212 119.67(17) . . ?
C220 C211 C212 121.28(18) . . ?
C213 C212 C211 119.35(18) . . ?
C213 C212 C221 120.63(18) . . ?
C211 C212 C221 120.02(18) . . ?
C212 C213 C214 121.52(18) . . ?
C213 C214 C215 121.04(18) . . ?
C213 C214 C219 118.75(18) . . ?
C215 C214 C219 120.16(18) . . ?
C216 C215 C214 120.91(19) . . ?
C215 C216 C217 119.25(19) . . ?
C218 C217 C216 121.41(19) . . ?
C217 C218 C219 121.11(19) . . ?
C220 C219 C218 122.65(18) . . ?
C220 C219 C214 120.17(17) . . ?
C218 C219 C214 117.12(18) . . ?
C211 C220 C219 118.70(17) . . ?
C211 C220 C222 119.79(17) . . ?
C219 C220 C222 121.45(17) . . ?
O221 C221 O222 123.73(18) . . ?
O221 C221 C212 120.71(18) . . ?
O222 C221 C212 115.55(18) . . ?
C220 C222 C223 114.53(16) . . ?
C224 C223 C232 118.46(18) . . ?
C224 C223 C222 119.85(18) . . ?
C232 C223 C222 121.62(17) . . ?
O224 C224 C223 119.04(18) . . ?
O224 C224 C225 119.59(17) . . ?
C223 C224 C225 121.37(19) . . ?
C226 C225 C224 119.47(18) . . ?
C226 C225 C233 119.99(19) . . ?
C224 C225 C233 120.52(19) . . ?
C225 C226 C227 121.41(19) . . ?
C226 C227 C228 121.06(19) . . ?
C226 C227 C232 118.77(19) . . ?
C228 C227 C232 120.07(19) . . ?
C229 C228 C227 121.2(2) . . ?
C228 C229 C230 119.4(2) . . ?
C231 C230 C229 121.1(2) . . ?
C230 C231 C232 121.2(2) . . ?
C227 C232 C231 117.05(19) . . ?
C227 C232 C223 120.20(18) . . ?
C231 C232 C223 122.68(18) . . ?
O233 C233 O234 124.15(19) . . ?
O233 C233 C225 119.79(19) . . ?
O234 C233 C225 116.04(19) . . ?
O1 C1 N2 126.1(5) . . ?
O1 C1 C5 126.5(4) . . ?
N2 C1 C5 107.4(4) . . ?
C1 N2 C6 123.7(7) . . ?
C1 N2 C3 114.7(5) . . ?
C6 N2 C3 121.1(6) . . ?
N2 C3 C4 103.1(6) . . ?
C5 C4 C3 103.7(5) . . ?
C1 C5 C4 105.1(5) . . ?
O1A C1A N2A 128.9(11) . . ?
O1A C1A C5A 117.1(15) . . ?
N2A C1A C5A 111.5(14) . . ?
C3A N2A C1A 113.5(11) . . ?
C3A N2A C6A 122.5(11) . . ?
C1A N2A C6A 123.7(10) . . ?
N2A C3A C4A 103.5(11) . . ?
C5A C4A C3A 106.0(14) . . ?
C4A C5A C1A 105.0(15) . . ?
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 C12 1.300(4) . ?
N11 C16 1.308(4) . ?
C12 C13 1.423(4) . ?
C12 C17 1.464(4) . ?
C13 C14 1.338(4) . ?
C13 C18 1.468(4) . ?
C14 C15 1.401(6) . ?
C15 C16 1.450(6) . ?
O211 C211 1.361(2) . ?
C211 C220 1.390(3) . ?
C211 C212 1.432(3) . ?
C212 C213 1.374(3) . ?
C212 C221 1.498(3) . ?
C213 C214 1.413(3) . ?
C214 C215 1.418(3) . ?
C214 C219 1.431(3) . ?
C215 C216 1.372(3) . ?
C216 C217 1.411(3) . ?
C217 C218 1.369(3) . ?
C218 C219 1.428(3) . ?
C219 C220 1.426(3) . ?
C220 C222 1.525(3) . ?
C221 O221 1.243(2) . ?
C221 O222 1.290(2) . ?
C222 C223 1.526(3) . ?
C223 C224 1.385(3) . ?
C223 C232 1.429(3) . ?
C224 O224 1.361(2) . ?
C224 C225 1.432(3) . ?
C225 C226 1.369(3) . ?
C225 C233 1.501(3) . ?
C226 C227 1.412(3) . ?
C227 C228 1.417(3) . ?
C227 C232 1.428(3) . ?
C228 C229 1.365(3) . ?
C229 C230 1.410(3) . ?
C230 C231 1.372(3) . ?
C231 C232 1.428(3) . ?
C233 O233 1.244(3) . ?
C233 O234 1.281(3) . ?
O1 C1 1.235(5) . ?
C1 N2 1.363(6) . ?
C1 C5 1.506(7) . ?
N2 C6 1.430(11) . ?
N2 C3 1.436(9) . ?
C3 C4 1.549(8) . ?
C4 C5 1.525(6) . ?
O1A C1A 1.30(2) . ?
C1A N2A 1.36(2) . ?
C1A C5A 1.457(16) . ?
N2A C3A 1.346(15) . ?
N2A C6A 1.448(14) . ?
C3A C4A 1.62(3) . ?
C4A C5A 1.44(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
O211 H211 O221 0.98(3) 1.63(3) 2.548(2) 155(3) .
N11 H11 O1 0.88 1.90 2.764(4) 165.6 .
O224 H224 O233 0.90(3) 1.71(3) 2.547(2) 153(3) .
O222 H222 O234 1.18(4) 1.28(4) 2.457(2) 177(4) 1_455
