#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:22:32 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180390 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/59/7205910.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_7205910
loop_
_publ_author_name
'Oelkers, Benjamin'
'Sundermeyer, Jörg'
_publ_section_title
;
 Pentaalkylmethylguanidinium methylcarbonates -- versatile precursors
 for the preparation of halide-free and metal-free guanidinium-based
 ILs
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              608
_journal_paper_doi               10.1039/c0gc00698j
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C7 H18 N3, Cl'
_chemical_formula_sum            'C7 H18 Cl N3'
_chemical_formula_weight         179.69
_chemical_name_systematic
;
?
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 104.10(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.622(3)
_cell_length_b                   7.8211(11)
_cell_length_c                   9.8987(17)
_cell_measurement_reflns_used    2571
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      3.0
_cell_volume                     1022.8(3)
_computing_cell_refinement       'STOE Cell'
_computing_data_collection       'STOE Expose'
_computing_data_reduction        'STOE Integrate'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'STOE IPDS 1'
_diffrn_measurement_method       'rotation method'
_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  0.0638
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4051
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.96
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.257
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         1080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.257
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0701
_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)+(0.1015P)²+1.6196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2253
_refine_ls_wR_factor_ref         0.2320
_reflns_number_gt                745
_reflns_number_total             1080
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0gc00698j.txt
_cod_data_source_block           Me6GuaCl
_cod_original_cell_volume        1022.9(3)
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               7205910
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
C1 C 0.5000 0.0000 0.0000 0.0368(18) Uani 1 4 d S . .
C2 C 0.3969(4) -0.2607(6) -0.0474(5) 0.0556(12) Uani 1 1 d . . .
H2A H 0.3828 -0.3209 0.0327 0.083 Uiso 1 1 calc R . .
H2B H 0.4017 -0.3437 -0.1196 0.083 Uiso 1 1 calc R . .
H2C H 0.3420 -0.1799 -0.0847 0.083 Uiso 1 1 calc R . .
C3 C 0.3596(5) 0.0000 0.1137(6) 0.069(2) Uani 1 2 d S . .
H3A H 0.3534 -0.0718 0.1923 0.103 Uiso 0.50 1 calc PR . .
H3B H 0.2920 0.0268 0.0562 0.103 Uiso 0.50 1 calc PR . .
H3C H 0.3947 0.1063 0.1488 0.103 Uiso 0.50 1 calc PR . .
C11 C 0.0000 0.5000 0.5000 0.0295(16) Uani 1 4 d S . .
C12 C 0.0646(4) 0.7627(6) 0.4177(5) 0.0595(13) Uani 1 1 d . . .
H12A H 0.0977 0.6803 0.3688 0.089 Uiso 1 1 calc R . .
H12B H 0.1161 0.8305 0.4820 0.089 Uiso 1 1 calc R . .
H12C H 0.0213 0.8388 0.3499 0.089 Uiso 1 1 calc R . .
C13 C 0.1854(4) 0.5000 0.5504(6) 0.070(2) Uani 1 2 d S . .
H13A H 0.1740 0.3951 0.5985 0.105 Uiso 0.50 1 calc PR . .
H13B H 0.2296 0.5768 0.6166 0.105 Uiso 0.50 1 calc PR . .
H13C H 0.2176 0.4714 0.4749 0.105 Uiso 0.50 1 calc PR . .
N1 N 0.5000 -0.1603(12) 0.0000 0.040(2) Uani 0.50 2 d SP . .
N2 N 0.4213(4) -0.0978(8) 0.0238(6) 0.0347(14) Uani 0.50 1 d P . .
N11 N 0.0000 0.6666(11) 0.5000 0.0350(19) Uani 0.50 2 d SP . .
N12 N 0.0829(4) 0.5896(8) 0.4892(6) 0.0352(14) Uani 0.50 1 d P . .
Cl1 Cl 0.18190(12) 0.0000 0.74894(15) 0.0586(7) Uani 1 2 d S . .
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'
Cl Cl 0.1484 0.1585 '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
N1 C1 N1 180.0 5_655 . ?
N1 C1 N2 123.6(3) . 5_655 ?
N1 C1 N2 56.4(3) . . ?
N2 C1 N2 180.0(6) 5_655 . ?
N2 C1 N2 112.9(5) . 2_655 ?
N2 C1 N2 67.1(5) . 6 ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N11 C11 N11 180.000(1) . 5_566 ?
N11 C11 N12 121.1(3) . 5_566 ?
N11 C11 N12 58.9(3) . . ?
N12 C11 N12 117.7(6) 2_556 . ?
N12 C11 N12 180.0(7) 5_566 . ?
N12 C11 N12 62.3(6) . 6_565 ?
N11 C12 H12A 109.5 . . ?
N11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N12 C13 H13A 109.5 . . ?
N12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 N1 N2 134.0(10) 2_655 . ?
N2 N1 C1 67.0(5) . . ?
N2 N1 C2 151.6(4) 2_655 . ?
N2 N1 C2 60.6(3) . . ?
C1 N1 C2 119.8(3) . . ?
C2 N1 C2 120.3(7) . 2_655 ?
N1 N2 C1 56.6(5) . . ?
N1 N2 N2 113.0(5) . 6 ?
C1 N2 N2 56.4(3) . 6 ?
N1 N2 C3 154.3(5) . . ?
C1 N2 C3 111.9(4) . . ?
N2 N2 C3 60.7(2) 6 . ?
C11 N11 N12 62.5(4) . . ?
N12 N11 N12 125.1(9) 2_556 . ?
N12 N11 C12 152.7(3) . 2_556 ?
C11 N11 C12 119.3(4) . . ?
N12 N11 C12 64.1(3) . . ?
C12 N11 C12 121.3(7) 2_556 . ?
N11 N12 C11 58.6(4) . . ?
N11 N12 N12 117.5(4) . 6_565 ?
C11 N12 N12 58.9(3) . 6_565 ?
N11 N12 C13 153.1(5) . . ?
C11 N12 C13 115.2(4) . . ?
N12 N12 C13 63.1(2) 6_565 . ?
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
C1 N1 1.254(10) . ?
C1 N2 1.384(6) . ?
C2 N1 1.578(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 N2 1.564(7) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C11 N11 1.303(9) . ?
C11 N12 1.355(6) . ?
C12 N11 1.534(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N12 1.548(8) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 N2 1.252(7) . ?
N1 C2 1.578(6) 2_655 ?
N2 N2 1.530(13) 6 ?
N11 N12 1.307(7) . ?
N11 C12 1.534(6) 2_556 ?
N12 N12 1.401(13) 6_565 ?
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
N2 C1 N1 N2 0.0 5_655 . . 2_655 ?
N2 C1 N1 N2 180.0 . . . 2_655 ?
N2 C1 N1 N2 180.0 6 . . 2_655 ?
N2 C1 N1 N2 180.0 5_655 . . . ?
N2 C1 N1 N2 180.0 2_655 . . . ?
N2 C1 N1 N2 0.0 6 . . . ?
N2 C1 N1 C2 -149.1(3) 5_655 . . . ?
N2 C1 N1 C2 30.9(3) . . . . ?
N2 C1 N1 C2 -149.1(3) 2_655 . . . ?
N2 C1 N1 C2 30.9(3) 6 . . . ?
N2 C1 N1 C2 30.9(3) 5_655 . . 2_655 ?
N2 C1 N1 C2 -149.1(3) . . . 2_655 ?
N2 C1 N1 C2 30.9(3) 2_655 . . 2_655 ?
N2 C1 N1 C2 -149.1(3) 6 . . 2_655 ?
N2 N1 N2 C1 0.0 2_655 . . . ?
C2 N1 N2 C1 -149.3(3) . . . . ?
C2 N1 N2 C1 110.6(14) 2_655 . . . ?
N2 N1 N2 N2 0.0 2_655 . . 6 ?
C1 N1 N2 N2 0.0 . . . 6 ?
C2 N1 N2 N2 -149.3(3) . . . 6 ?
C2 N1 N2 N2 110.6(14) 2_655 . . 6 ?
N2 N1 N2 C3 -69.9(13) 2_655 . . . ?
C1 N1 N2 C3 -69.9(13) . . . . ?
C2 N1 N2 C3 140.8(14) . . . . ?
C2 N1 N2 C3 41(3) 2_655 . . . ?
N1 C1 N2 N1 180.0 5_655 . . . ?
N2 C1 N2 N1 0.0 2_655 . . . ?
N2 C1 N2 N1 180.0 6 . . . ?
N1 C1 N2 N2 0.0 5_655 . . 6 ?
N1 C1 N2 N2 180.0 . . . 6 ?
N2 C1 N2 N2 180.0 2_655 . . 6 ?
N1 C1 N2 C3 -26.0(5) 5_655 . . . ?
N1 C1 N2 C3 154.0(5) . . . . ?
N2 C1 N2 C3 154.0(5) 2_655 . . . ?
N2 C1 N2 C3 -26.0(5) 6 . . . ?
N12 C11 N11 N12 0.0 5_566 . . 2_556 ?
N12 C11 N11 N12 180.0 . . . 2_556 ?
N12 C11 N11 N12 180.0 6_565 . . 2_556 ?
N12 C11 N11 N12 180.0 2_556 . . . ?
N12 C11 N11 N12 180.0 5_566 . . . ?
N12 C11 N11 N12 0.0 6_565 . . . ?
N12 C11 N11 C12 31.1(4) 2_556 . . 2_556 ?
N12 C11 N11 C12 31.1(4) 5_566 . . 2_556 ?
N12 C11 N11 C12 -148.9(4) . . . 2_556 ?
N12 C11 N11 C12 -148.9(4) 6_565 . . 2_556 ?
N12 C11 N11 C12 -148.9(4) 2_556 . . . ?
N12 C11 N11 C12 -148.9(4) 5_566 . . . ?
N12 C11 N11 C12 31.1(4) . . . . ?
N12 C11 N11 C12 31.1(4) 6_565 . . . ?
N12 N11 N12 C11 0.0 2_556 . . . ?
C12 N11 N12 C11 101.4(14) 2_556 . . . ?
C12 N11 N12 C11 -150.0(3) . . . . ?
C11 N11 N12 N12 0.0 . . . 6_565 ?
N12 N11 N12 N12 0.0 2_556 . . 6_565 ?
C12 N11 N12 N12 101.4(14) 2_556 . . 6_565 ?
C12 N11 N12 N12 -150.0(3) . . . 6_565 ?
C11 N11 N12 C13 -84.1(12) . . . . ?
N12 N11 N12 C13 -84.1(12) 2_556 . . . ?
C12 N11 N12 C13 17(3) 2_556 . . . ?
C12 N11 N12 C13 125.9(13) . . . . ?
N11 C11 N12 N11 180.0 5_566 . . . ?
N12 C11 N12 N11 180.0 6_565 . . . ?
N11 C11 N12 N12 180.0 . . . 6_565 ?
N11 C11 N12 N12 0.0 5_566 . . 6_565 ?
N11 C11 N12 C13 150.2(6) . . . . ?
N11 C11 N12 C13 -29.8(6) 5_566 . . . ?
N12 C11 N12 C13 -29.8(6) 6_565 . . . ?
