#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:12:59 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179656 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/09/4510971.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_4510971
loop_
_publ_author_name
'Carvalho, Simão P.'
'Wang, Ruiyao'
'Wang, Haotian'
'Ball, Brian'
'Lebel, Olivier'
_publ_section_title
;
 The Brønsted-Lowry Reaction Revisited: Glass-Forming Properties of
 Salts of 1,5-Dimexylbiguanide
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2734
_journal_paper_doi               10.1021/cg1002435
_journal_volume                  10
_journal_year                    2010
_chemical_formula_sum            'C42 H56 N10 O4'
_chemical_formula_weight         764.97
_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                93.946(3)
_cell_angle_beta                 109.581(2)
_cell_angle_gamma                114.975(2)
_cell_formula_units_Z            1
_cell_length_a                   9.7875(19)
_cell_length_b                   10.587(2)
_cell_length_c                   12.438(3)
_cell_measurement_reflns_used    1603
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      23.07
_cell_measurement_theta_min      2.43
_cell_volume                     1066.9(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0543
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10803
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_correction_T_min  0.9767
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             410
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0507
_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)+(0.0683P)²+0.0888P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1430
_reflns_number_gt                2691
_reflns_number_total             4169
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg1002435_si_004.cif
_cod_data_source_block           ol06
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4510971
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
O1 O 0.32458(16) 0.13062(14) 0.95343(13) 0.0335(4) Uani 1 1 d .
O2 O 0.32710(18) 0.32479(15) 1.03441(14) 0.0423(4) Uani 1 1 d .
N1 N 0.7696(2) 0.49123(19) 0.88006(16) 0.0335(4) Uani 1 1 d .
H1N H 0.749(3) 0.564(3) 0.902(2) 0.053(7) Uiso 1 1 d .
N2 N 0.6236(2) 0.3822(2) 0.98449(17) 0.0362(5) Uani 1 1 d .
H2NA H 0.620(3) 0.460(3) 1.000(2) 0.053(8) Uiso 1 1 d .
H2NB H 0.535(3) 0.294(3) 0.982(2) 0.069(8) Uiso 1 1 d .
N3 N 0.6887(2) 0.24825(17) 0.87059(15) 0.0309(4) Uani 1 1 d .
N4 N 0.7253(2) 0.16759(18) 1.04496(15) 0.0335(4) Uani 1 1 d .
H4B H 0.7830 0.2559 1.0896 0.040 Uiso 1 1 calc R
H4C H 0.7063 0.0941 1.0774 0.040 Uiso 1 1 calc R
N5 N 0.5927(2) 0.00622(18) 0.86984(16) 0.0300(4) Uani 1 1 d .
H5N H 0.602(2) -0.051(2) 0.9149(18) 0.031(6) Uiso 1 1 d .
C1 C 0.8618(2) 0.5206(2) 0.81047(17) 0.0285(5) Uani 1 1 d .
C2 C 0.8678(2) 0.6317(2) 0.75631(18) 0.0319(5) Uani 1 1 d .
H2A H 0.8063 0.6785 0.7642 0.038 Uiso 1 1 calc R
C3 C 0.9617(3) 0.6758(2) 0.69088(18) 0.0361(5) Uani 1 1 d .
C4 C 1.0491(3) 0.6049(2) 0.67930(19) 0.0382(6) Uani 1 1 d .
H4A H 1.1133 0.6336 0.6341 0.046 Uiso 1 1 calc R
C5 C 1.0446(3) 0.4928(2) 0.73253(19) 0.0358(5) Uani 1 1 d .
C6 C 0.9507(3) 0.4514(2) 0.79931(18) 0.0343(5) Uani 1 1 d .
H6A H 0.9478 0.3759 0.8371 0.041 Uiso 1 1 calc R
C7 C 0.9695(3) 0.7989(3) 0.6351(2) 0.0563(7) Uani 1 1 d .
H7A H 0.8864 0.8242 0.6409 0.085 Uiso 1 1 calc R
H7B H 0.9482 0.7706 0.5521 0.085 Uiso 1 1 calc R
H7C H 1.0791 0.8821 0.6760 0.085 Uiso 1 1 calc R
C8 C 1.1419(3) 0.4186(3) 0.7192(2) 0.0547(7) Uani 1 1 d .
H8A H 1.1462 0.3592 0.7760 0.082 Uiso 1 1 calc R
H8B H 1.2541 0.4908 0.7339 0.082 Uiso 1 1 calc R
H8C H 1.0888 0.3576 0.6392 0.082 Uiso 1 1 calc R
C9 C 0.6954(2) 0.3701(2) 0.91274(18) 0.0284(5) Uani 1 1 d .
C10 C 0.6669(2) 0.1451(2) 0.92818(18) 0.0277(5) Uani 1 1 d .
C11 C 0.5075(2) -0.0571(2) 0.74770(18) 0.0298(5) Uani 1 1 d .
C12 C 0.4246(3) -0.0018(2) 0.6688(2) 0.0390(5) Uani 1 1 d .
H12A H 0.4253 0.0848 0.6956 0.047 Uiso 1 1 calc R
C13 C 0.3403(3) -0.0728(3) 0.5503(2) 0.0452(6) Uani 1 1 d .
C14 C 0.3405(3) -0.1992(3) 0.5130(2) 0.0496(7) Uani 1 1 d .
H14A H 0.2842 -0.2470 0.4317 0.060 Uiso 1 1 calc R
C15 C 0.4203(3) -0.2578(2) 0.5910(2) 0.0426(6) Uani 1 1 d .
C16 C 0.5030(3) -0.1859(2) 0.70927(19) 0.0354(5) Uani 1 1 d .
H16A H 0.5570 -0.2250 0.7645 0.042 Uiso 1 1 calc R
C17 C 0.2480(3) -0.0140(3) 0.4641(2) 0.0655(8) Uani 1 1 d .
H17A H 0.2973 0.0901 0.4943 0.098 Uiso 1 1 calc R
H17B H 0.1325 -0.0600 0.4536 0.098 Uiso 1 1 calc R
H17C H 0.2543 -0.0337 0.3882 0.098 Uiso 1 1 calc R
C18 C 0.4226(3) -0.3933(3) 0.5493(2) 0.0636(8) Uani 1 1 d .
H18A H 0.4570 -0.4321 0.6167 0.095 Uiso 1 1 calc R
H18B H 0.5002 -0.3718 0.5114 0.095 Uiso 1 1 calc R
H18C H 0.3121 -0.4642 0.4927 0.095 Uiso 1 1 calc R
C19 C 0.2526(3) 0.2011(2) 0.96823(19) 0.0317(5) Uani 1 1 d .
C20 C 0.0675(3) 0.1295(2) 0.9028(2) 0.0417(6) Uani 1 1 d .
H20A H 0.0386 0.1097 0.8170 0.050 Uiso 1 1 calc R
H20B H 0.0265 0.1954 0.9218 0.050 Uiso 1 1 calc R
C21 C -0.0157(3) -0.0105(2) 0.9356(2) 0.0378(5) Uani 1 1 d .
H21A H 0.027(2) -0.076(2) 0.9192(17) 0.031(5) Uiso 1 1 d .
H21B H -0.138(3) -0.060(3) 0.885(2) 0.053(7) 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
C9 N1 C1 130.72(19) .
C9 N1 H1N 114.1(15) .
C1 N1 H1N 114.9(15) .
C9 N2 H2NA 119.4(17) .
C9 N2 H2NB 115.1(16) .
H2NA N2 H2NB 118(2) .
C9 N3 C10 120.86(18) .
C10 N4 H4B 120.0 .
C10 N4 H4C 120.0 .
H4B N4 H4C 120.0 .
C10 N5 C11 129.58(19) .
C10 N5 H5N 113.8(14) .
C11 N5 H5N 116.6(14) .
C6 C1 C2 119.85(19) .
C6 C1 N1 124.22(19) .
C2 C1 N1 115.83(18) .
C3 C2 C1 121.3(2) .
C3 C2 H2A 119.4 .
C1 C2 H2A 119.4 .
C2 C3 C4 118.4(2) .
C2 C3 C7 120.4(2) .
C4 C3 C7 121.1(2) .
C3 C4 C5 121.3(2) .
C3 C4 H4A 119.3 .
C5 C4 H4A 119.3 .
C4 C5 C6 119.2(2) .
C4 C5 C8 120.2(2) .
C6 C5 C8 120.7(2) .
C1 C6 C5 119.9(2) .
C1 C6 H6A 120.0 .
C5 C6 H6A 120.0 .
C3 C7 H7A 109.5 .
C3 C7 H7B 109.5 .
H7A C7 H7B 109.5 .
C3 C7 H7C 109.5 .
H7A C7 H7C 109.5 .
H7B C7 H7C 109.5 .
C5 C8 H8A 109.5 .
C5 C8 H8B 109.5 .
H8A C8 H8B 109.5 .
C5 C8 H8C 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
N3 C9 N2 123.87(19) .
N3 C9 N1 121.30(18) .
N2 C9 N1 114.73(19) .
N3 C10 N4 124.71(19) .
N3 C10 N5 120.72(19) .
N4 C10 N5 114.36(18) .
C12 C11 C16 120.2(2) .
C12 C11 N5 123.60(19) .
C16 C11 N5 116.13(18) .
C11 C12 C13 120.0(2) .
C11 C12 H12A 120.0 .
C13 C12 H12A 120.0 .
C14 C13 C12 119.1(2) .
C14 C13 C17 120.7(2) .
C12 C13 C17 120.2(2) .
C15 C14 C13 121.9(2) .
C15 C14 H14A 119.1 .
C13 C14 H14A 119.1 .
C14 C15 C16 118.3(2) .
C14 C15 C18 121.4(2) .
C16 C15 C18 120.3(2) .
C15 C16 C11 120.6(2) .
C15 C16 H16A 119.7 .
C11 C16 H16A 119.7 .
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 .
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 .
O2 C19 O1 123.1(2) .
O2 C19 C20 119.56(19) .
O1 C19 C20 117.3(2) .
C19 C20 C21 111.33(18) .
C19 C20 H20A 109.4 .
C21 C20 H20A 109.4 .
C19 C20 H20B 109.4 .
C21 C20 H20B 109.4 .
H20A C20 H20B 108.0 .
C21 C21 C20 113.0(2) 2_557
C21 C21 H21A 106.5(11) 2_557
C20 C21 H21A 109.9(12) .
C21 C21 H21B 110.5(13) 2_557
C20 C21 H21B 109.5(13) .
H21A C21 H21B 107.3(18) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C19 1.265(2) .
O2 C19 1.252(2) .
N1 C9 1.350(3) .
N1 C1 1.409(3) .
N1 H1N 0.92(3) .
N2 C9 1.337(3) .
N2 H2NA 0.86(3) .
N2 H2NB 0.96(3) .
N3 C9 1.325(2) .
N3 C10 1.328(2) .
N4 C10 1.332(3) .
N4 H4B 0.8800 .
N4 H4C 0.8800 .
N5 C10 1.347(3) .
N5 C11 1.411(3) .
N5 H5N 0.86(2) .
C1 C6 1.385(3) .
C1 C2 1.385(3) .
C2 C3 1.384(3) .
C2 H2A 0.9500 .
C3 C4 1.388(3) .
C3 C7 1.503(3) .
C4 C5 1.390(3) .
C4 H4A 0.9500 .
C5 C6 1.396(3) .
C5 C8 1.507(3) .
C6 H6A 0.9500 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C11 C12 1.383(3) .
C11 C16 1.391(3) .
C12 C13 1.388(3) .
C12 H12A 0.9500 .
C13 C14 1.387(4) .
C13 C17 1.507(3) .
C14 C15 1.386(3) .
C14 H14A 0.9500 .
C15 C16 1.388(3) .
C15 C18 1.503(3) .
C16 H16A 0.9500 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 C20 1.512(3) .
C20 C21 1.520(3) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C21 1.508(5) 2_557
C21 H21A 0.99(2) .
C21 H21B 1.01(3) .
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 H1N O2 0.92(3) 1.89(3) 2.787(2) 164(2) 2_667
N2 H2NB O1 0.96(3) 1.95(3) 2.885(2) 167(2) .
N2 H2NB O2 0.96(3) 2.47(3) 2.991(2) 114.2(19) .
N2 H2NA O2 0.86(3) 2.22(3) 2.970(3) 146(2) 2_667
N4 H4C O1 0.88 2.26 2.987(2) 140.3 2_657
N5 H5N O1 0.86(2) 1.96(2) 2.797(2) 164(2) 2_657
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_4
C9 N1 C1 C6 -27.4(3) .
C9 N1 C1 C2 156.1(2) .
C6 C1 C2 C3 -0.1(3) .
N1 C1 C2 C3 176.48(18) .
C1 C2 C3 C4 0.7(3) .
C1 C2 C3 C7 -178.6(2) .
C2 C3 C4 C5 -0.5(3) .
C7 C3 C4 C5 178.8(2) .
C3 C4 C5 C6 -0.3(3) .
C3 C4 C5 C8 -179.5(2) .
C2 C1 C6 C5 -0.7(3) .
N1 C1 C6 C5 -177.00(19) .
C4 C5 C6 C1 0.9(3) .
C8 C5 C6 C1 -179.9(2) .
C10 N3 C9 N2 -26.1(3) .
C10 N3 C9 N1 157.64(19) .
C1 N1 C9 N3 -6.3(3) .
C1 N1 C9 N2 177.1(2) .
C9 N3 C10 N4 -33.9(3) .
C9 N3 C10 N5 151.68(19) .
C11 N5 C10 N3 -10.2(3) .
C11 N5 C10 N4 174.85(18) .
C10 N5 C11 C12 -28.9(3) .
C10 N5 C11 C16 154.4(2) .
C16 C11 C12 C13 -1.8(3) .
N5 C11 C12 C13 -178.37(19) .
C11 C12 C13 C14 0.2(3) .
C11 C12 C13 C17 179.3(2) .
C12 C13 C14 C15 1.0(4) .
C17 C13 C14 C15 -178.1(2) .
C13 C14 C15 C16 -0.5(3) .
C13 C14 C15 C18 -178.7(2) .
C14 C15 C16 C11 -1.1(3) .
C18 C15 C16 C11 177.2(2) .
C12 C11 C16 C15 2.2(3) .
N5 C11 C16 C15 179.09(18) .
O2 C19 C20 C21 -120.3(2) .
O1 C19 C20 C21 59.1(3) .
C19 C20 C21 C21 61.6(3) 2_557
