#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:58:52 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180366 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/35/7203593.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_7203593
loop_
_publ_author_name
'Haynes, Delia A.'
'Jones, William'
'Motherwell, W. D. Samuel'
_publ_section_title
;
 Cocrystallisation of succinic and fumaric acids with lutidines: a
 systematic study
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              830
_journal_paper_doi               10.1039/b610294h
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C7 H10 N 1+,0.5(C4 H2 O4 2-),C4 H4 O4'
_chemical_formula_sum            'C13 H15 N O6'
_chemical_formula_weight         281.26
_chemical_name_common            '3,4 lutidine fumarate'
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.305(2)
_cell_angle_beta                 104.584(2)
_cell_angle_gamma                107.975(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0478(2)
_cell_length_b                   10.0870(3)
_cell_length_c                   10.8570(3)
_cell_measurement_reflns_used    3656
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     674.12(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6479
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.53
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3049
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0421
_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)+(0.0302P)²+0.3119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1015
_reflns_number_gt                2565
_reflns_number_total             3049
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b610294h.txt
_cod_data_source_block           wj0324
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        674.12(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7203593
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.20706(19) 0.20194(13) 0.40151(12) 0.0271(3) Uani 1 1 d . . .
H11N H 0.1133 0.2009 0.4421 0.032 Uiso 1 1 calc R . .
C11 C 0.1509(2) 0.09657(16) 0.28507(15) 0.0270(3) Uani 1 1 d . . .
H11 H 0.0123 0.0220 0.2488 0.032 Uiso 1 1 calc R . .
C12 C 0.2925(2) 0.09517(16) 0.21714(14) 0.0255(3) Uani 1 1 d . . .
C13 C 0.4950(2) 0.20926(16) 0.27226(15) 0.0260(3) Uani 1 1 d . . .
C14 C 0.5458(2) 0.31398(16) 0.39362(15) 0.0292(3) Uani 1 1 d . . .
H14 H 0.6827 0.3906 0.4329 0.035 Uiso 1 1 calc R . .
C15 C 0.4002(2) 0.30810(16) 0.45772(15) 0.0294(3) Uani 1 1 d . . .
H15 H 0.4369 0.3793 0.5417 0.035 Uiso 1 1 calc R . .
C16 C 0.2314(3) -0.02772(19) 0.09203(16) 0.0399(4) Uani 1 1 d . . .
H16A H 0.0849 -0.0953 0.0702 0.060 Uiso 1 1 calc R . .
H16B H 0.3265 -0.0806 0.1056 0.060 Uiso 1 1 calc R . .
H16C H 0.2427 0.0120 0.0181 0.060 Uiso 1 1 calc R . .
C17 C 0.6558(3) 0.2140(2) 0.20310(18) 0.0398(4) Uani 1 1 d . . .
H17A H 0.7908 0.2951 0.2592 0.060 Uiso 1 1 calc R . .
H17B H 0.6047 0.2291 0.1165 0.060 Uiso 1 1 calc R . .
H17C H 0.6768 0.1211 0.1886 0.060 Uiso 1 1 calc R . .
C21 C 0.7711(2) 0.08890(14) 0.47855(13) 0.0197(3) Uani 1 1 d . . .
C22 C 0.5920(2) 0.05604(14) 0.53269(13) 0.0204(3) Uani 1 1 d . . .
H22 H 0.6114 0.1184 0.6177 0.025 Uiso 1 1 calc R . .
O21 O 0.92674(15) 0.21056(10) 0.53914(10) 0.0253(2) Uani 1 1 d . . .
O22 O 0.76103(16) -0.00068(11) 0.37568(10) 0.0295(2) Uani 1 1 d . . .
C31 C 0.0748(2) 0.53480(16) 0.19180(15) 0.0270(3) Uani 1 1 d . . .
C32 C 0.0337(2) 0.47078(16) 0.04635(14) 0.0275(3) Uani 1 1 d . . .
H32 H 0.0570 0.3831 0.0180 0.033 Uiso 1 1 calc R . .
O31 O 0.01917(17) 0.64843(12) 0.21885(11) 0.0347(3) Uani 1 1 d D . .
H31 H 0.049(3) 0.693(2) 0.3172(15) 0.042 Uiso 1 1 d D . .
O32 O 0.15194(19) 0.48558(13) 0.27476(11) 0.0383(3) Uani 1 1 d . . .
C41 C -0.3961(2) 0.68900(15) 0.13213(13) 0.0237(3) Uani 1 1 d . . .
C42 C -0.4862(2) 0.52797(15) 0.06400(14) 0.0237(3) Uani 1 1 d . . .
H42 H -0.5251 0.4634 0.1136 0.028 Uiso 1 1 calc R . .
O41 O -0.41013(17) 0.72113(11) 0.25343(10) 0.0316(3) Uani 1 1 d D . .
H41 H -0.348(3) 0.8259(16) 0.2969(17) 0.038 Uiso 1 1 d D . .
O42 O -0.32139(18) 0.77960(11) 0.08213(11) 0.0345(3) Uani 1 1 d . . .
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'
O O 0.0106 0.0060 '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'
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
C15 N11 C11 122.09(12) . . ?
C15 N11 H11N 119.0 . . ?
C11 N11 H11N 119.0 . . ?
N11 C11 C12 120.84(13) . . ?
N11 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 118.03(13) . . ?
C11 C12 C16 119.99(13) . . ?
C13 C12 C16 121.94(13) . . ?
C14 C13 C12 118.75(12) . . ?
C14 C13 C17 120.63(14) . . ?
C12 C13 C17 120.58(14) . . ?
C15 C14 C13 120.59(13) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
N11 C15 C14 119.64(14) . . ?
N11 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O22 C21 O21 122.49(12) . . ?
O22 C21 C22 120.04(11) . . ?
O21 C21 C22 117.45(11) . . ?
C22 C22 C21 122.92(15) 2_656 . ?
C22 C22 H22 118.5 2_656 . ?
C21 C22 H22 118.5 . . ?
O32 C31 O31 124.71(13) . . ?
O32 C31 C32 122.09(14) . . ?
O31 C31 C32 113.20(13) . . ?
C32 C32 C31 123.80(17) 2_565 . ?
C32 C32 H32 118.1 2_565 . ?
C31 C32 H32 118.1 . . ?
C31 O31 H31 113.1(11) . . ?
O42 C41 O41 124.28(13) . . ?
O42 C41 C42 124.08(13) . . ?
O41 C41 C42 111.63(12) . . ?
C42 C42 C41 121.69(17) 2_465 . ?
C42 C42 H42 119.2 2_465 . ?
C41 C42 H42 119.2 . . ?
C41 O41 H41 110.5(11) . . ?
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 C15 1.3325(19) . ?
N11 C11 1.3418(19) . ?
N11 H11N 0.8800 . ?
C11 C12 1.3837(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.408(2) . ?
C12 C16 1.492(2) . ?
C13 C14 1.384(2) . ?
C13 C17 1.5036(19) . ?
C14 C15 1.371(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C21 O22 1.2488(16) . ?
C21 O21 1.2665(16) . ?
C21 C22 1.4990(17) . ?
C22 C22 1.324(3) 2_656 ?
C22 H22 0.9500 . ?
C31 O32 1.2099(19) . ?
C31 O31 1.3213(19) . ?
C31 C32 1.4880(19) . ?
C32 C32 1.331(3) 2_565 ?
C32 H32 0.9500 . ?
O31 H31 1.005(14) . ?
C41 O42 1.2105(17) . ?
C41 O41 1.3240(16) . ?
C41 C42 1.4844(19) . ?
C42 C42 1.323(3) 2_465 ?
C42 H42 0.9500 . ?
O41 H41 0.964(14) . ?
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 H11N O21 0.88 1.89 2.7715(14) 175.9 1_455
O31 H31 O21 1.005(14) 1.591(15) 2.5769(14) 166.0(18) 2_666
O41 H41 O22 0.964(14) 1.607(14) 2.5706(14) 177.3(18) 1_465
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
C15 N11 C11 C12 -0.8(2) . . . . ?
N11 C11 C12 C13 -1.4(2) . . . . ?
N11 C11 C12 C16 176.43(14) . . . . ?
C11 C12 C13 C14 2.4(2) . . . . ?
C16 C12 C13 C14 -175.45(14) . . . . ?
C11 C12 C13 C17 -179.90(14) . . . . ?
C16 C12 C13 C17 2.3(2) . . . . ?
C12 C13 C14 C15 -1.1(2) . . . . ?
C17 C13 C14 C15 -178.90(14) . . . . ?
C11 N11 C15 C14 2.1(2) . . . . ?
C13 C14 C15 N11 -1.1(2) . . . . ?
O22 C21 C22 C22 -9.0(3) . . . 2_656 ?
O21 C21 C22 C22 169.48(17) . . . 2_656 ?
O32 C31 C32 C32 -174.04(17) . . . 2_565 ?
O31 C31 C32 C32 5.9(2) . . . 2_565 ?
O42 C41 C42 C42 -8.1(3) . . . 2_465 ?
O41 C41 C42 C42 171.07(16) . . . 2_465 ?
