#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:58:52 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180366 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/35/7203596.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_7203596
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         '2(C7 H9 N), C4 H6 O4'
_chemical_formula_sum            'C18 H24 N2 O4'
_chemical_formula_weight         332.39
_chemical_name_common            '3,5 lutidine succinic acid co-crystal'
_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                 95.67(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.464(2)
_cell_length_b                   4.9696(10)
_cell_length_c                   17.113(3)
_cell_measurement_reflns_used    9867
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     885.6(3)
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0570
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5880
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         3.91
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.004
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0580
_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)+(0.0619P)²+0.2795P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1453
_reflns_number_gt                1336
_reflns_number_total             2025
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b610294h.txt
_cod_data_source_block           wj0433
_cod_original_cell_volume        885.5(3)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7203596
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 0.81915(16) -0.2285(3) 0.89971(10) 0.0347(4) Uani 1 1 d . . .
C12 C 0.7347(2) -0.3291(4) 0.84321(12) 0.0344(5) Uani 1 1 d . . .
H12 H 0.650(2) -0.242(4) 0.8401(12) 0.033(5) Uiso 1 1 d . . .
C13 C 0.76253(19) -0.5379(4) 0.79426(12) 0.0350(5) Uani 1 1 d . . .
C14 C 0.8852(2) -0.6450(4) 0.80545(12) 0.0337(5) Uani 1 1 d . . .
H14 H 0.907(2) -0.794(5) 0.7736(13) 0.046(6) Uiso 1 1 d . . .
C15 C 0.97546(18) -0.5455(4) 0.86302(11) 0.0306(5) Uani 1 1 d . . .
C16 C 0.9371(2) -0.3367(4) 0.90862(12) 0.0330(5) Uani 1 1 d . . .
H16 H 0.996(2) -0.262(4) 0.9507(13) 0.038(6) Uiso 1 1 d . . .
C17 C 0.6622(2) -0.6430(5) 0.73233(15) 0.0517(6) Uani 1 1 d . . .
H17A H 0.6826 -0.8292 0.7194 0.078 Uiso 0.50 1 calc PR . .
H17B H 0.6612 -0.5313 0.6851 0.078 Uiso 0.50 1 calc PR . .
H17C H 0.5776 -0.6367 0.7523 0.078 Uiso 0.50 1 calc PR . .
H17D H 0.5983 -0.5022 0.7185 0.078 Uiso 0.50 1 calc PR . .
H17E H 0.6197 -0.8001 0.7528 0.078 Uiso 0.50 1 calc PR . .
H17F H 0.7033 -0.6948 0.6855 0.078 Uiso 0.50 1 calc PR . .
C18 C 1.1087(2) -0.6604(5) 0.87691(13) 0.0413(5) Uani 1 1 d . . .
H18A H 1.1047 -0.8393 0.9006 0.062 Uiso 1 1 calc R . .
H18B H 1.1622 -0.5420 0.9124 0.062 Uiso 1 1 calc R . .
H18C H 1.1461 -0.6749 0.8268 0.062 Uiso 1 1 calc R . .
C21 C 0.61601(18) 0.2336(4) 0.96575(11) 0.0303(5) Uani 1 1 d . . .
C22 C 0.56752(18) 0.4557(4) 1.01413(12) 0.0315(5) Uani 1 1 d . . .
H22A H 0.6259 0.6121 1.0130 0.038 Uiso 1 1 calc R . .
H22B H 0.5694 0.3945 1.0693 0.038 Uiso 1 1 calc R . .
O21 O 0.55295(14) 0.1270(3) 0.91129(9) 0.0417(4) Uani 1 1 d . . .
O22 O 0.73648(13) 0.1645(3) 0.98904(9) 0.0383(4) Uani 1 1 d . . .
H22 H 0.771(3) 0.012(7) 0.954(2) 0.100(11) Uiso 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'
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 117.78(18) . . ?
N11 C12 C13 123.64(19) . . ?
N11 C12 H12 113.8(12) . . ?
C13 C12 H12 122.6(12) . . ?
C12 C13 C14 116.89(18) . . ?
C12 C13 C17 120.77(19) . . ?
C14 C13 C17 122.3(2) . . ?
C13 C14 C15 121.17(19) . . ?
C13 C14 H14 119.3(13) . . ?
C15 C14 H14 119.5(13) . . ?
C16 C15 C14 117.01(18) . . ?
C16 C15 C18 120.83(18) . . ?
C14 C15 C18 122.16(19) . . ?
N11 C16 C15 123.51(19) . . ?
N11 C16 H16 116.1(13) . . ?
C15 C16 H16 120.3(13) . . ?
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 . . ?
C13 C17 H17D 109.5 . . ?
H17A C17 H17D 141.1 . . ?
H17B C17 H17D 56.3 . . ?
H17C C17 H17D 56.3 . . ?
C13 C17 H17E 109.5 . . ?
H17A C17 H17E 56.3 . . ?
H17B C17 H17E 141.1 . . ?
H17C C17 H17E 56.3 . . ?
H17D C17 H17E 109.5 . . ?
C13 C17 H17F 109.5 . . ?
H17A C17 H17F 56.3 . . ?
H17B C17 H17F 56.3 . . ?
H17C C17 H17F 141.1 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O21 C21 O22 123.14(18) . . ?
O21 C21 C22 124.05(18) . . ?
O22 C21 C22 112.82(16) . . ?
C21 C22 C22 113.2(2) . 3_667 ?
C21 C22 H22A 108.9 . . ?
C22 C22 H22A 108.9 3_667 . ?
C21 C22 H22B 108.9 . . ?
C22 C22 H22B 108.9 3_667 . ?
H22A C22 H22B 107.7 . . ?
C21 O22 H22 112.5(17) . . ?
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 1.340(3) . ?
N11 C16 1.341(3) . ?
C12 C13 1.383(3) . ?
C12 H12 0.99(2) . ?
C13 C14 1.386(3) . ?
C13 C17 1.510(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.96(2) . ?
C15 C16 1.381(3) . ?
C15 C18 1.504(3) . ?
C16 H16 0.97(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17D 0.9800 . ?
C17 H17E 0.9800 . ?
C17 H17F 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 O21 1.210(2) . ?
C21 O22 1.329(2) . ?
C21 C22 1.498(3) . ?
C22 C22 1.513(4) 3_667 ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
O22 H22 1.05(4) . ?
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
O22 H22 N11 1.05(4) 1.62(4) 2.676(2) 178(3) .
