#------------------------------------------------------------------------------
#$Date: 2017-03-05 07:26:38 +0200 (Sun, 05 Mar 2017) $
#$Revision: 193875 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/59/7055930.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_7055930
loop_
_publ_author_name
'Zavgorodnya, Oleksandra'
'Shamshina, Julia L.'
'Mittenthal, Max'
'McCrary, Parker D.'
'Rachiero, Giovanni P.'
'Titi, Hatem M.'
'Rogers, Robin D.'
_publ_section_title
;
 Polyethylene glycol derivatization of the non-active ion in active
 pharmaceutical ingredient ionic liquids enhances transdermal delivery
;
_journal_issue                   4
_journal_name_full               'New J. Chem.'
_journal_page_first              1499
_journal_paper_doi               10.1039/C6NJ03709G
_journal_volume                  41
_journal_year                    2017
_chemical_formula_sum            'C12 H17 N O3'
_chemical_formula_weight         223.26
_chemical_melting_point          385.15
_chemical_name_systematic        'methylpyrrolidinium salicylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-11-28 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.981(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.655(5)
_cell_length_b                   9.012(4)
_cell_length_c                   12.686(5)
_cell_measurement_reflns_used    4162
_cell_measurement_temperature    196(2)
_cell_measurement_theta_max      35.005
_cell_measurement_theta_min      3.006
_cell_volume                     1197.8(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (sheldrick 2015)'
_diffrn_ambient_temperature      196(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27642
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.005
_diffrn_reflns_theta_min         3.006
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         5227
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0506
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0808P)²+0.1787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1509
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4162
_reflns_number_total             5227
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6nj03709g2.cif
_cod_data_source_block           s1
_cod_depositor_comments          'Adding full bibliography for 7055930.cif.'
_cod_original_cell_volume        1197.9(8)
_cod_database_code               7055930
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.81628(7) 0.79027(8) 0.08885(7) 0.02898(15) Uani 1 1 d . .
H1 H 0.8755(12) 0.7140(15) 0.1242(11) 0.035 Uiso 1 1 d . U
C2 C 0.79764(12) 0.87305(12) 0.18226(9) 0.0424(2) Uani 1 1 d . .
H2A H 0.7919 0.8037 0.2403 0.051 Uiso 1 1 calc R U
H2B H 0.7189 0.9336 0.1479 0.051 Uiso 1 1 calc R U
C3 C 0.91419(15) 0.97065(18) 0.23855(12) 0.0600(4) Uani 1 1 d . .
H3A H 0.9759 0.9271 0.3137 0.072 Uiso 1 1 calc R U
H3B H 0.8899 1.0706 0.2542 0.072 Uiso 1 1 calc R U
C4 C 0.97341(12) 0.98061(15) 0.15176(13) 0.0518(3) Uani 1 1 d . .
H4A H 0.9815 1.0854 0.1326 0.062 Uiso 1 1 calc R U
H4B H 1.0591 0.9343 0.1853 0.062 Uiso 1 1 calc R U
C5 C 0.88230(9) 0.89708(10) 0.04300(9) 0.03478(18) Uani 1 1 d . .
H5A H 0.8203 0.9656 -0.0151 0.042 Uiso 1 1 calc R U
H5B H 0.9295 0.8438 0.0060 0.042 Uiso 1 1 calc R U
C6 C 0.69717(9) 0.72570(12) -0.00280(9) 0.0388(2) Uani 1 1 d . .
H6A H 0.7159 0.6764 -0.0624 0.058 Uiso 1 1 calc R U
H6B H 0.6346 0.8048 -0.0396 0.058 Uiso 1 1 calc R U
H6C H 0.6623 0.6532 0.0330 0.058 Uiso 1 1 calc R U
C7 C 1.07997(7) 0.39018(8) 0.32296(6) 0.02163(13) Uani 1 1 d . .
C8 C 1.10126(9) 0.34147(9) 0.43504(7) 0.02964(16) Uani 1 1 d . .
H8A H 1.0532 0.3832 0.4718 0.036 Uiso 1 1 calc R U
C9 C 1.19179(10) 0.23289(11) 0.49301(8) 0.0376(2) Uani 1 1 d . .
H9 H 1.2050 0.2002 0.5687 0.045 Uiso 1 1 calc R U
C10 C 1.26339(10) 0.17189(10) 0.43948(9) 0.0367(2) Uani 1 1 d . .
H10 H 1.3261 0.0987 0.4795 0.044 Uiso 1 1 calc R U
C11 C 1.24343(8) 0.21756(9) 0.32828(8) 0.03153(17) Uani 1 1 d . .
H11 H 1.2923 0.1756 0.2924 0.038 Uiso 1 1 calc R U
C12 C 1.15108(7) 0.32566(8) 0.26897(7) 0.02347(14) Uani 1 1 d . .
C13 C 0.98637(7) 0.51354(8) 0.26456(7) 0.02354(14) Uani 1 1 d . .
O14 O 0.92952(7) 0.57413(8) 0.31639(7) 0.03583(16) Uani 1 1 d . .
O15 O 0.97308(6) 0.55334(7) 0.16194(5) 0.02958(13) Uani 1 1 d . .
O16 O 1.13270(7) 0.36508(7) 0.15940(5) 0.03134(14) Uani 1 1 d . .
H16 H 1.0762(14) 0.4389(17) 0.1375(13) 0.047 Uiso 1 1 d . U
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
C6 N1 C2 113.94(8)
C6 N1 C5 114.24(8)
C2 N1 C5 105.34(8)
N1 C2 C3 104.64(10)
C2 C3 C4 106.77(10)
C5 C4 C3 105.46(10)
N1 C5 C4 103.82(9)
C8 C7 C12 118.84(7)
C8 C7 C13 119.89(7)
C12 C7 C13 121.23(7)
C9 C8 C7 120.86(8)
C8 C9 C10 119.74(8)
C11 C10 C9 120.46(8)
C10 C11 C12 119.95(8)
O16 C12 C11 118.11(7)
O16 C12 C7 121.75(7)
C11 C12 C7 120.14(8)
O14 C13 O15 123.59(8)
O14 C13 C7 120.16(8)
O15 C13 C7 116.22(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C6 1.4845(13)
N1 C2 1.4944(13)
N1 C5 1.4998(13)
C2 C3 1.510(2)
C3 C4 1.537(2)
C4 C5 1.5212(16)
C7 C8 1.4024(12)
C7 C12 1.4112(11)
C7 C13 1.5056(11)
C8 C9 1.3899(14)
C9 C10 1.3987(15)
C10 C11 1.3878(14)
C11 C12 1.4015(11)
C12 O16 1.3576(11)
C13 O14 1.2455(10)
C13 O15 1.2926(11)
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
N1 H1 O14 0.938(13) 2.566(13) 3.2450(14) 129.6(10) .
N1 H1 O15 0.938(13) 1.772(13) 2.6972(12) 168.2(12) .
C2 H2A O14 0.99 2.54 3.1975(16) 124.1 .
C2 H2B O14 0.99 2.34 3.2147(15) 146.5 2_655
C6 H6A O16 0.98 2.58 3.4639(15) 149.6 3_765
C6 H6B O14 0.98 2.53 3.4610(15) 158.0 4_575
O16 H16 O15 0.891(15) 1.712(16) 2.5285(11) 151.1(15) .
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
C6 N1 C2 C3 -160.85(9)
C5 N1 C2 C3 -34.86(11)
N1 C2 C3 C4 18.48(13)
C2 C3 C4 C5 4.26(14)
C6 N1 C5 C4 163.29(8)
C2 N1 C5 C4 37.48(10)
C3 C4 C5 N1 -25.22(12)
C12 C7 C8 C9 0.79(12)
C13 C7 C8 C9 -176.79(7)
C7 C8 C9 C10 0.44(14)
C8 C9 C10 C11 -0.89(15)
C9 C10 C11 C12 0.07(14)
C10 C11 C12 O16 -178.68(8)
C10 C11 C12 C7 1.18(13)
C8 C7 C12 O16 178.26(7)
C13 C7 C12 O16 -4.20(11)
C8 C7 C12 C11 -1.59(11)
C13 C7 C12 C11 175.95(7)
C8 C7 C13 O14 1.26(11)
C12 C7 C13 O14 -176.26(7)
C8 C7 C13 O15 179.24(7)
C12 C7 C13 O15 1.72(10)
