#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:09:43 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180378 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/47/7204752.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_7204752
loop_
_publ_author_name
'Holbrey, John D.'
'Turner, Megan B.'
'Reichert, W. Matthew'
'Rogers, Robin D.'
_publ_section_title
;
 New ionic liquids containing an appended hydroxyl functionality from
 the atom-efficient, one-pot reaction of 1-methylimidazole and acid
 with propylene oxide
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              731
_journal_paper_doi               10.1039/b311717k
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C31 H33 B N2 O'
_chemical_formula_weight         460.40
_chemical_melting_point          411
_chemical_name_systematic
'1-(2-hydroxypropyl)-3-methylimidazolium tetraphenylborate'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                96.211(5)
_cell_angle_beta                 111.392(5)
_cell_angle_gamma                94.957(5)
_cell_formula_units_Z            2
_cell_length_a                   10.771(3)
_cell_length_b                   11.201(3)
_cell_length_c                   11.612(4)
_cell_measurement_reflns_used    941
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      46.44
_cell_measurement_theta_min      5.77
_cell_volume                     1284.7(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  ccd
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5698
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         1.85
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.53
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             492
_exptl_crystal_size_max          1.50
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.045(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         3634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0403
_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)+(0.0856P)²+0.0701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1153
_reflns_number_gt                3103
_reflns_number_total             3634
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b311717k.txt
_cod_data_source_block           propyl
_cod_original_cell_volume        1284.6(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204752
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
B B 0.14065(17) 0.23359(16) 0.79326(17) 0.0323(4) Uani 1 1 d . . .
N1 N 0.70217(12) 0.18367(11) 0.96850(12) 0.0352(3) Uani 1 1 d . . .
N2 N 0.71168(13) 0.29170(11) 1.13809(12) 0.0364(3) Uani 1 1 d . . .
O1 O 0.43838(12) 0.04933(11) 0.84045(11) 0.0431(3) Uani 1 1 d . . .
H1A H 0.363(3) 0.077(2) 0.802(2) 0.095(9) Uiso 1 1 d . . .
C2 C 0.67609(16) 0.18182(15) 1.07187(15) 0.0369(4) Uani 1 1 d . . .
H2A H 0.6363(16) 0.1113(16) 1.0964(15) 0.038(4) Uiso 1 1 d . . .
C4 C 0.76380(17) 0.36716(16) 1.07548(16) 0.0421(4) Uani 1 1 d . . .
H4A H 0.7934(18) 0.4522(18) 1.1056(17) 0.053(5) Uiso 1 1 d . . .
C5 C 0.75676(17) 0.30007(16) 0.96970(17) 0.0418(4) Uani 1 1 d . . .
H5A H 0.7769(19) 0.3173(17) 0.8999(18) 0.053(5) Uiso 1 1 d . . .
C6 C 0.7065(2) 0.32553(18) 1.26150(18) 0.0459(5) Uani 1 1 d . . .
H6A H 0.673(2) 0.2514(19) 1.2855(18) 0.065(6) Uiso 1 1 d . . .
H6B H 0.652(2) 0.390(2) 1.2563(19) 0.068(6) Uiso 1 1 d . . .
H6C H 0.795(2) 0.3473(19) 1.327(2) 0.068(6) Uiso 1 1 d . . .
C7 C 0.66678(17) 0.08315(16) 0.86608(16) 0.0399(4) Uani 1 1 d . . .
H7A H 0.6775(17) 0.0076(17) 0.9014(15) 0.042(5) Uiso 1 1 d . . .
H7B H 0.7294(18) 0.0920(15) 0.8222(16) 0.044(5) Uiso 1 1 d . . .
C8 C 0.52321(17) 0.07902(15) 0.77448(15) 0.0390(4) Uani 1 1 d . . .
H8A H 0.5098(16) 0.1616(16) 0.7537(14) 0.039(4) Uiso 1 1 d . . .
C9 C 0.4910(3) -0.01272(19) 0.6587(2) 0.0567(5) Uani 1 1 d . . .
H9A H 0.399(3) -0.012(2) 0.595(2) 0.074(7) Uiso 1 1 d . . .
H9B H 0.509(2) -0.096(2) 0.6833(19) 0.070(6) Uiso 1 1 d . . .
H9C H 0.554(2) 0.007(2) 0.618(2) 0.075(7) Uiso 1 1 d . . .
C10 C 0.00192(15) 0.28481(13) 0.70656(13) 0.0310(4) Uani 1 1 d . . .
C11 C -0.12768(16) 0.22449(15) 0.67893(15) 0.0376(4) Uani 1 1 d . . .
H11A H -0.1372(18) 0.1435(17) 0.7044(16) 0.050(5) Uiso 1 1 d . . .
C12 C -0.24448(17) 0.27065(16) 0.61205(16) 0.0424(4) Uani 1 1 d . . .
H12A H -0.333(2) 0.2220(17) 0.5983(16) 0.053(5) Uiso 1 1 d . . .
C13 C -0.23679(17) 0.37958(16) 0.56782(15) 0.0393(4) Uani 1 1 d . . .
H13A H -0.3156(19) 0.4158(16) 0.5203(16) 0.046(5) Uiso 1 1 d . . .
C14 C -0.11078(17) 0.44194(15) 0.59113(15) 0.0385(4) Uani 1 1 d . . .
H14A H -0.1066(18) 0.5192(18) 0.5586(16) 0.049(5) Uiso 1 1 d . . .
C15 C 0.00437(16) 0.39441(14) 0.65895(14) 0.0350(4) Uani 1 1 d . . .
H15A H 0.0918(18) 0.4398(15) 0.6705(15) 0.041(4) Uiso 1 1 d . . .
C16 C 0.26348(15) 0.28683(13) 0.75012(14) 0.0328(4) Uani 1 1 d . . .
C17 C 0.25007(17) 0.26901(15) 0.62432(16) 0.0388(4) Uani 1 1 d . . .
H17A H 0.1711(18) 0.2199(16) 0.5589(16) 0.043(5) Uiso 1 1 d . . .
C18 C 0.34653(18) 0.31931(16) 0.58271(18) 0.0445(4) Uani 1 1 d . . .
H18A H 0.3278(17) 0.2999(15) 0.4911(17) 0.045(5) Uiso 1 1 d . . .
C19 C 0.46081(18) 0.39296(15) 0.66706(18) 0.0448(5) Uani 1 1 d . . .
H19A H 0.526(2) 0.4298(18) 0.6388(18) 0.061(6) Uiso 1 1 d . . .
C20 C 0.47844(17) 0.41403(15) 0.79197(18) 0.0403(4) Uani 1 1 d . . .
H20A H 0.5601(18) 0.4668(15) 0.8572(16) 0.045(5) Uiso 1 1 d . . .
C21 C 0.38221(15) 0.36069(14) 0.83226(16) 0.0357(4) Uani 1 1 d . . .
H21A H 0.4005(16) 0.3794(15) 0.9258(16) 0.038(4) Uiso 1 1 d . . .
C22 C 0.10822(14) 0.08326(14) 0.76940(14) 0.0314(4) Uani 1 1 d . . .
C23 C 0.05386(16) 0.02294(15) 0.84415(16) 0.0371(4) Uani 1 1 d . . .
H23A H 0.0500(16) 0.0679(15) 0.9174(16) 0.040(4) Uiso 1 1 d . . .
C24 C 0.00665(17) -0.10038(15) 0.81850(16) 0.0410(4) Uani 1 1 d . . .
H24A H -0.0316(19) -0.1352(17) 0.8750(18) 0.059(5) Uiso 1 1 d . . .
C25 C 0.01412(17) -0.17052(15) 0.71594(16) 0.0414(4) Uani 1 1 d . . .
H25A H -0.0196(18) -0.2544(17) 0.6971(16) 0.048(5) Uiso 1 1 d . . .
C26 C 0.07020(16) -0.11616(15) 0.64123(16) 0.0390(4) Uani 1 1 d . . .
H26A H 0.0752(17) -0.1654(15) 0.5665(17) 0.046(5) Uiso 1 1 d . . .
C27 C 0.11556(15) 0.00782(15) 0.66800(15) 0.0350(4) Uani 1 1 d . . .
H27A H 0.1514(17) 0.0439(15) 0.6118(16) 0.044(5) Uiso 1 1 d . . .
C28 C 0.17855(14) 0.28149(13) 0.94266(14) 0.0307(4) Uani 1 1 d . . .
C29 C 0.10687(16) 0.35954(14) 0.98886(15) 0.0337(4) Uani 1 1 d . . .
H29A H 0.0283(17) 0.3882(14) 0.9260(15) 0.036(4) Uiso 1 1 d . . .
C30 C 0.14049(17) 0.39717(15) 1.11597(15) 0.0380(4) Uani 1 1 d . . .
H30A H 0.0934(19) 0.4526(17) 1.1475(17) 0.051(5) Uiso 1 1 d . . .
C31 C 0.24798(17) 0.35799(14) 1.20352(15) 0.0382(4) Uani 1 1 d . . .
H31A H 0.2719(16) 0.3857(14) 1.2958(16) 0.040(4) Uiso 1 1 d . . .
C32 C 0.32178(17) 0.28043(15) 1.16170(16) 0.0389(4) Uani 1 1 d . . .
H32A H 0.3949(19) 0.2521(15) 1.2228(17) 0.046(5) Uiso 1 1 d . . .
C33 C 0.28757(16) 0.24359(14) 1.03530(15) 0.0358(4) Uani 1 1 d . . .
H33A H 0.3368(17) 0.1858(15) 1.0064(15) 0.041(4) 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'
B B 0.0013 0.0007 '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
C28 B C10 110.44(12) . . ?
C28 B C22 108.26(12) . . ?
C10 B C22 107.11(12) . . ?
C28 B C16 110.01(12) . . ?
C10 B C16 107.07(12) . . ?
C22 B C16 113.91(12) . . ?
C2 N1 C5 108.02(14) . . ?
C2 N1 C7 125.80(14) . . ?
C5 N1 C7 125.92(14) . . ?
C2 N2 C4 108.49(14) . . ?
C2 N2 C6 125.77(14) . . ?
C4 N2 C6 125.58(14) . . ?
N2 C2 N1 109.00(14) . . ?
C5 C4 N2 107.00(15) . . ?
C4 C5 N1 107.49(15) . . ?
N1 C7 C8 111.18(13) . . ?
O1 C8 C9 111.06(15) . . ?
O1 C8 C7 106.29(13) . . ?
C9 C8 C7 111.96(16) . . ?
C15 C10 C11 114.47(15) . . ?
C15 C10 B 122.66(13) . . ?
C11 C10 B 122.82(14) . . ?
C12 C11 C10 122.94(16) . . ?
C13 C12 C11 120.39(16) . . ?
C12 C13 C14 118.87(16) . . ?
C13 C14 C15 119.65(16) . . ?
C14 C15 C10 123.66(15) . . ?
C17 C16 C21 114.72(14) . . ?
C17 C16 B 121.29(13) . . ?
C21 C16 B 123.78(14) . . ?
C18 C17 C16 123.19(16) . . ?
C19 C18 C17 119.86(18) . . ?
C20 C19 C18 119.23(16) . . ?
C19 C20 C21 120.07(16) . . ?
C20 C21 C16 122.91(16) . . ?
C27 C22 C23 114.47(14) . . ?
C27 C22 B 124.63(13) . . ?
C23 C22 B 120.45(13) . . ?
C24 C23 C22 123.41(15) . . ?
C25 C24 C23 119.83(16) . . ?
C24 C25 C26 119.05(16) . . ?
C25 C26 C27 120.10(16) . . ?
C26 C27 C22 123.10(15) . . ?
C29 C28 C33 114.62(14) . . ?
C29 C28 B 124.39(14) . . ?
C33 C28 B 120.99(13) . . ?
C30 C29 C28 122.99(16) . . ?
C31 C30 C29 120.53(15) . . ?
C30 C31 C32 118.35(16) . . ?
C33 C32 C31 120.68(16) . . ?
C32 C33 C28 122.84(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
B C28 1.646(2) . ?
B C10 1.659(2) . ?
B C22 1.661(2) . ?
B C16 1.664(2) . ?
N1 C2 1.330(2) . ?
N1 C5 1.380(2) . ?
N1 C7 1.460(2) . ?
N2 C2 1.323(2) . ?
N2 C4 1.381(2) . ?
N2 C6 1.465(2) . ?
O1 C8 1.430(2) . ?
C4 C5 1.342(3) . ?
C7 C8 1.517(2) . ?
C8 C9 1.511(3) . ?
C10 C15 1.402(2) . ?
C10 C11 1.404(2) . ?
C11 C12 1.393(2) . ?
C12 C13 1.381(3) . ?
C13 C14 1.389(2) . ?
C14 C15 1.391(2) . ?
C16 C17 1.405(2) . ?
C16 C21 1.409(2) . ?
C17 C18 1.398(2) . ?
C18 C19 1.387(3) . ?
C19 C20 1.383(3) . ?
C20 C21 1.399(2) . ?
C22 C27 1.404(2) . ?
C22 C23 1.408(2) . ?
C23 C24 1.391(2) . ?
C24 C25 1.386(2) . ?
C25 C26 1.386(2) . ?
C26 C27 1.394(2) . ?
C28 C29 1.402(2) . ?
C28 C33 1.407(2) . ?
C29 C30 1.391(2) . ?
C30 C31 1.376(2) . ?
C31 C32 1.390(2) . ?
C32 C33 1.381(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
C2 H2A O1 0.984(18) 2.211(18) 3.193(2) 175.9(13) 2_657
C4 H4A C15 0.962(19) 3.027(19) 3.785(2) 136.7(14) 2_667
C8 H8A C17 0.990(17) 3.072(16) 3.790(3) 130.5(12) .
C8 H8A C18 0.990(17) 2.984(17) 3.862(3) 148.4(12) .
C8 H8A C19 0.990(17) 2.902(18) 3.888(3) 174.4(12) .
C8 H8A C20 0.990(17) 2.883(17) 3.818(3) 157.8(12) .
C8 H8A C21 0.990(17) 2.949(16) 3.718(2) 135.2(12) .
O1 H1A B 0.87(3) 3.07(3) 3.866(2) 153(2) .
O1 H1A C16 0.87(3) 2.70(3) 3.428(2) 141(2) .
O1 H1A C22 0.87(3) 2.64(3) 3.411(2) 148(2) .
O1 H1A C27 0.87(3) 2.55(3) 3.280(2) 142(2) .
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
N1 C7 C8 C9 171.86(15) . . . . ?
C2 N1 C7 C8 84.25(19) . . . . ?
C5 N1 C7 C8 -89.21(19) . . . . ?
N1 C7 C8 O1 -66.71(17) . . . . ?
