# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_author_address             
;
Faculty of Chemistry,
Adam Mickiewicz University,
Grunwaldzka 6, 60-780 Pozna\'n
Poland
;
loop_
_publ_author_footnote
;
Faculty of Chemistry,
Adam Mickiewicz University,
Grunwaldzka 6, 60-780 Pozna\'n
Poland
;
_publ_contact_author_address     
;
Faculty of Chemistry,
Adam Mickiewicz University,
Grunwaldzka 6, 60-780 Pozna\'n
Poland
;
_publ_contact_author_email       katran@amu.edu.pl
_publ_contact_author_fax         +48(61)8291505
_publ_contact_author_phone       +48(61)8291443
_publ_contact_author_name        'Andrzej Katrusiak'
_publ_section_title              
;
?
;
_publ_author_name                'Andrzej Katrusiak'

data_NmetdabcoBr12
_database_code_depnum_ccdc_archive 'CCDC 869507'
#TrackingRef '- structures.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
N-methyl-1,4-diazabicyclo[2.2.2]octanium bromide dimethanol cocrystal
;
_chemical_name_common            
;N-methyl-1,4-diazabicyclo(2.2.2)octanium bromide dimethanol
cocrystal
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H15 N2, 2(C H4 O), Br'
_chemical_formula_sum            'C9 H23 Br N2 O2'
_chemical_formula_weight         271.20

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/m'
_symmetry_space_group_name_Hall  '-P 2yb'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   9.270(2)
_cell_length_b                   6.7304(13)
_cell_length_c                   9.710(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.60(4)
_cell_angle_gamma                90.00
_cell_volume                     577.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       1200000
_cell_measurement_reflns_used    4082
_cell_measurement_theta_min      3.81
_cell_measurement_theta_max      28.23

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    3.540
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.71
_exptl_absorpt_process_details   
;
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Pozna\'n.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
;
Data were collected at room temperature and pressure of 1.2(5) GPa
(1200000 kPa) with the crystal obtained by the in-situ high-pressure
crystallization technique.
Pressure was determined by monitoring the shift of the ruby
R1-fluorescence line.
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4082
_diffrn_reflns_av_R_equivalents  0.1142
_diffrn_reflns_av_sigmaI/netI    0.0792
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.81
_diffrn_reflns_theta_max         28.23
_reflns_number_total             447
_reflns_number_gt                332
_reflns_threshold_expression     >2sigma(I)

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
The DAC imposes severe restrictions on which reflections can be collected,
resulting in a low data:parameter ratio.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0779P)^2^+0.4758P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         447
_refine_ls_number_parameters     40
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1599
_refine_ls_wR_factor_gt          0.1434
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_restrained_S_all      1.164
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.23763(18) 0.7500 0.0816(4) 0.040(3) Uani 1 2 d S . .
N1 N 0.7172(14) 0.7500 0.153(3) 0.026(3) Uiso 1 2 d S . .
C2 C 0.8805(19) 0.7500 0.142(5) 0.031(3) Uiso 1 2 d S . .
H2A H 0.8995 0.8675 0.0920 0.037 Uiso 0.50 1 calc PR . .
H2B H 0.8995 0.6325 0.0920 0.037 Uiso 0.50 1 calc PR . .
C3 C 0.983(2) 0.7500 0.311(5) 0.041(4) Uiso 1 2 d S . .
H3A H 1.0477 0.6337 0.3284 0.049 Uiso 0.50 1 calc PR . .
H3B H 1.0477 0.8663 0.3284 0.049 Uiso 0.50 1 calc PR . .
N4 N 0.8995(13) 0.7500 0.411(3) 0.028(3) Uiso 1 2 d S . .
C5 C 0.7998(13) 0.9313(13) 0.380(3) 0.037(3) Uiso 1 1 d . . .
H5B H 0.7448 0.9388 0.4503 0.044 Uiso 1 1 calc R . .
H5A H 0.8630 1.0487 0.3914 0.044 Uiso 1 1 calc R . .
C6 C 0.6925(13) 0.9322(13) 0.237(3) 0.031(2) Uiso 1 1 d . . .
H6A H 0.7055 1.0519 0.1859 0.037 Uiso 1 1 calc R . .
H6B H 0.5902 0.9314 0.2433 0.037 Uiso 1 1 calc R . .
C7 C 0.6145(19) 0.7500 0.003(5) 0.030(3) Uiso 1 2 d S . .
H7A H 0.5371 0.6517 -0.0060 0.036 Uiso 0.50 1 calc PR . .
H7B H 0.6711 0.7196 -0.0620 0.036 Uiso 0.50 1 calc PR . .
H7C H 0.5687 0.8786 -0.0192 0.036 Uiso 0.50 1 calc PR . .
C1M C 0.8880(15) 0.7500 0.768(4) 0.045(4) Uiso 1 2 d SD . .
H1MA H 0.8895 0.6298 0.7209 0.053 Uiso 0.50 1 d P . .
H1MB H 0.8978 0.7176 0.8726 0.053 Uiso 0.50 1 d P . .
H1MC H 0.9803 0.8259 0.7748 0.053 Uiso 0.50 1 d P . .
O1M O 0.7539(14) 0.861(2) 0.716(4) 0.051(4) Uiso 0.50 1 d PD . .
H1M H 0.6821 0.9441 0.7522 0.061 Uiso 0.50 1 d P . .
C2M C 0.4188(19) 0.7500 0.466(4) 0.038(5) Uiso 1 2 d SD . .
H2MA H 0.4133 0.6156 0.4317 0.045 Uiso 0.50 1 calc PR . .
H2MB H 0.4959 0.8203 0.4384 0.045 Uiso 0.50 1 calc PR . .
H2MC H 0.3230 0.8142 0.4244 0.045 Uiso 0.50 1 calc PR . .
O2M O 0.4544(15) 0.7500 0.618(4) 0.049(4) Uiso 1 2 d SD . .
H2M H 0.5466 0.7500 0.6540 0.059 Uiso 1 2 calc SR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0394(12) 0.0377(8) 0.045(9) 0.000 0.018(3) 0.000

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N1 C7 1.48(4) . ?
N1 C6 1.52(2) . ?
N1 C6 1.52(2) 4_575 ?
N1 C2 1.551(18) . ?
C2 C3 1.63(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N4 1.41(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N4 C5 1.505(12) 4_575 ?
N4 C5 1.505(12) . ?
C5 C6 1.45(4) . ?
C5 H5B 0.9700 . ?
C5 H5A 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C1M O1M 1.408(5) 4_575 ?
C1M O1M 1.408(5) . ?
C1M H1MA 0.933(19) . ?
C1M H1MB 1.01(4) . ?
C1M H1MC 0.982(11) . ?
O1M O1M 1.50(3) 4_575 ?
O1M H1M 1.01(2) . ?
C2M O2M 1.410(5) . ?
C2M H2MA 0.9600 . ?
C2M H2MB 0.9600 . ?
C2M H2MC 0.9600 . ?
O2M H2M 0.8200 . ?

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
C7 N1 C6 111.5(12) . . ?
C7 N1 C6 111.5(12) . 4_575 ?
C6 N1 C6 107(2) . 4_575 ?
C7 N1 C2 106(3) . . ?
C6 N1 C2 110.2(12) . . ?
C6 N1 C2 110.2(12) 4_575 . ?
N1 C2 C3 102(3) . . ?
N1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
N1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
N4 C3 C2 114.8(16) . . ?
N4 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
N4 C3 H3B 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.5 . . ?
C3 N4 C5 107.1(19) . 4_575 ?
C3 N4 C5 107.1(19) . . ?
C5 N4 C5 108.3(11) 4_575 . ?
C6 C5 N4 113.5(18) . . ?
C6 C5 H5B 108.9 . . ?
N4 C5 H5B 108.9 . . ?
C6 C5 H5A 108.9 . . ?
N4 C5 H5A 108.9 . . ?
H5B C5 H5A 107.7 . . ?
C5 C6 N1 109.7(12) . . ?
C5 C6 H6A 109.7 . . ?
N1 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
N1 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1M C1M O1M 64.3(13) 4_575 . ?
O1M C1M H1MA 60.4(9) 4_575 . ?
O1M C1M H1MA 115(2) . . ?
O1M C1M H1MB 92.6(19) 4_575 . ?
O1M C1M H1MB 106(2) . . ?
H1MA C1M H1MB 107.3(16) . . ?
O1M C1M H1MC 163(4) 4_575 . ?
O1M C1M H1MC 113.8(10) . . ?
H1MA C1M H1MC 110(2) . . ?
H1MB C1M H1MC 104(3) . . ?
C1M O1M O1M 57.8(6) . 4_575 ?
C1M O1M H1M 141(3) . . ?
O1M O1M H1M 123.6(9) 4_575 . ?
O2M C2M H2MA 109.5 . . ?
O2M C2M H2MB 109.5 . . ?
H2MA C2M H2MB 109.5 . . ?
O2M C2M H2MC 109.5 . . ?
H2MA C2M H2MC 109.5 . . ?
H2MB C2M H2MC 109.5 . . ?
C2M O2M H2M 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.290
_diffrn_reflns_theta_full        28.23
_diffrn_measured_fraction_theta_full 0.290
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.078

#===END

data_NmetdabcoBr17
_database_code_depnum_ccdc_archive 'CCDC 869508'
#TrackingRef '- structures.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
N-methyl-1,4-diazabicyclo[2.2.2]octanium bromide dimethanol cocrystal
;
_chemical_name_common            
;N-methyl-1,4-diazabicyclo(2.2.2)octanium bromide dimethanol
cocrystal
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H15 N2, 2(C H4 O), Br'
_chemical_formula_sum            'C9 H23 Br N2 O2'
_chemical_formula_weight         271.20

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/m'
_symmetry_space_group_name_Hall  '-P 2yb'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   9.194(4)
_cell_length_b                   6.653(3)
_cell_length_c                   9.643(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.72(7)
_cell_angle_gamma                90.00
_cell_volume                     561.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       1700000
_cell_measurement_reflns_used    3313
_cell_measurement_theta_min      3.85
_cell_measurement_theta_max      28.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    3.639
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_T_max  0.62
_exptl_absorpt_process_details   
;
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Pozna\'n.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
;
Data were collected at room temperature and pressure of 1.7(5) GPa
(1700000 kPa) with the crystal obtained by the in-situ high-pressure
crystallization technique.
Pressure was determined by monitoring the shift of the ruby
R1-fluorescence line.
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3313
_diffrn_reflns_av_R_equivalents  0.2220
_diffrn_reflns_av_sigmaI/netI    0.1550
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.85
_diffrn_reflns_theta_max         28.49
_reflns_number_total             370
_reflns_number_gt                229
_reflns_threshold_expression     >2sigma(I)

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
The DAC imposes severe restrictions on which reflections can be collected,
resulting in a low data:parameter ratio.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1232P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         370
_refine_ls_number_parameters     43
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1801
_refine_ls_R_factor_gt           0.1125
_refine_ls_wR_factor_ref         0.2507
_refine_ls_wR_factor_gt          0.2178
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.2374(4) 0.7500 0.0821(9) 0.049(8) Uani 1 2 d S . .
N1 N 0.713(3) 0.7500 0.150(7) 0.021(5) Uiso 1 2 d S . .
C2 C 0.877(4) 0.7500 0.136(11) 0.035(8) Uiso 1 2 d S . .
H2A H 0.8967 0.8691 0.0867 0.042 Uiso 0.50 1 calc PR . .
H2B H 0.8967 0.6309 0.0867 0.042 Uiso 0.50 1 calc PR . .
C3 C 0.975(4) 0.7500 0.306(10) 0.029(7) Uiso 1 2 d S . .
H3A H 1.0407 0.6330 0.3227 0.035 Uiso 0.50 1 calc PR . .
H3B H 1.0407 0.8670 0.3227 0.035 Uiso 0.50 1 calc PR . .
N4 N 0.903(3) 0.7500 0.417(7) 0.027(6) Uiso 1 2 d S . .
C5 C 0.800(2) 0.933(2) 0.374(6) 0.030(5) Uiso 1 1 d . . .
H5B H 0.7454 0.9487 0.4448 0.036 Uiso 1 1 calc R . .
H5A H 0.8641 1.0502 0.3807 0.036 Uiso 1 1 calc R . .
C6 C 0.692(2) 0.932(2) 0.235(7) 0.027(5) Uiso 1 1 d . . .
H6A H 0.7037 1.0530 0.1835 0.032 Uiso 1 1 calc R . .
H6B H 0.5903 0.9314 0.2447 0.032 Uiso 1 1 calc R . .
C7 C 0.608(4) 0.7500 -0.002(9) 0.025(7) Uiso 1 2 d S . .
H7A H 0.5299 0.6507 -0.0115 0.029 Uiso 0.50 1 calc PR . .
H7B H 0.6647 0.7192 -0.0683 0.029 Uiso 0.50 1 calc PR . .
H7C H 0.5618 0.8802 -0.0249 0.029 Uiso 0.50 1 calc PR . .
C1M C 0.892(3) 0.7500 0.772(9) 0.050(9) Uiso 1 2 d SD . .
H1MA H 0.8895 0.6298 0.7209 0.060 Uiso 0.50 1 d P . .
H1MB H 0.8978 0.7176 0.8726 0.060 Uiso 0.50 1 d P . .
H1MC H 0.9803 0.8259 0.7748 0.060 Uiso 0.50 1 d P . .
O1M O 0.755(3) 0.860(4) 0.728(9) 0.056(8) Uiso 0.50 1 d PD . .
H1M H 0.6821 0.9441 0.7522 0.067 Uiso 0.50 1 d P . .
C2M C 0.416(4) 0.7500 0.460(9) 0.047(16) Uiso 1 2 d SD . .
H2MA H 0.4102 0.6140 0.4253 0.056 Uiso 0.50 1 calc PR . .
H2MB H 0.4916 0.8222 0.4300 0.056 Uiso 0.50 1 calc PR . .
H2MC H 0.3183 0.8138 0.4200 0.056 Uiso 0.50 1 calc PR . .
O2M O 0.456(3) 0.7500 0.613(8) 0.041(9) Uiso 1 2 d SD . .
H2M H 0.5488 0.7500 0.6471 0.049 Uiso 1 2 calc SR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.043(3) 0.0374(17) 0.07(2) 0.000 0.022(7) 0.000

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N1 C7 1.49(9) . ?
N1 C6 1.51(5) . ?
N1 C6 1.51(5) 4_575 ?
N1 C2 1.55(4) . ?
C2 C3 1.61(14) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N4 1.41(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N4 C5 1.52(3) 4_575 ?
N4 C5 1.52(3) . ?
C5 C6 1.40(8) . ?
C5 H5B 0.9700 . ?
C5 H5A 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C1M O1M 1.409(5) 4_575 ?
C1M O1M 1.409(5) . ?
C1M H1MA 0.94(4) . ?
C1M H1MB 0.98(8) . ?
C1M H1MC 0.95(2) . ?
O1M O1M 1.47(5) 4_575 ?
O1M H1M 0.95(4) . ?
C2M O2M 1.40(5) . ?
C2M H2MA 0.9600 . ?
C2M H2MB 0.9600 . ?
C2M H2MC 0.9600 . ?
O2M H2M 0.8200 . ?

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
C7 N1 C6 113(2) . . ?
C7 N1 C6 113(2) . 4_575 ?
C6 N1 C6 107(5) . 4_575 ?
C7 N1 C2 106(5) . . ?
C6 N1 C2 109(3) . . ?
C6 N1 C2 109(3) 4_575 . ?
N1 C2 C3 100(6) . . ?
N1 C2 H2A 111.8 . . ?
C3 C2 H2A 111.8 . . ?
N1 C2 H2B 111.8 . . ?
C3 C2 H2B 111.8 . . ?
H2A C2 H2B 109.5 . . ?
N4 C3 C2 122(3) . . ?
N4 C3 H3A 106.9 . . ?
C2 C3 H3A 106.9 . . ?
N4 C3 H3B 106.9 . . ?
C2 C3 H3B 106.9 . . ?
H3A C3 H3B 106.7 . . ?
C3 N4 C5 101(4) . 4_575 ?
C3 N4 C5 101(4) . . ?
C5 N4 C5 106(2) 4_575 . ?
C6 C5 N4 117(3) . . ?
C6 C5 H5B 108.0 . . ?
N4 C5 H5B 108.0 . . ?
C6 C5 H5A 108.0 . . ?
N4 C5 H5A 108.0 . . ?
H5B C5 H5A 107.2 . . ?
C5 C6 N1 111(2) . . ?
C5 C6 H6A 109.5 . . ?
N1 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1M C1M O1M 63(2) 4_575 . ?
O1M C1M H1MA 61.4(19) 4_575 . ?
O1M C1M H1MA 114(4) . . ?
O1M C1M H1MB 88(4) 4_575 . ?
O1M C1M H1MB 101(5) . . ?
H1MA C1M H1MB 109(3) . . ?
O1M C1M H1MC 165(8) 4_575 . ?
O1M C1M H1MC 114(2) . . ?
H1MA C1M H1MC 110(5) . . ?
H1MB C1M H1MC 108(6) . . ?
C1M O1M O1M 58.6(12) . 4_575 ?
C1M O1M H1M 150(8) . . ?
O1M O1M H1M 125.9(19) 4_575 . ?
O2M C2M H2MA 109.5 . . ?
O2M C2M H2MB 109.5 . . ?
H2MA C2M H2MB 109.5 . . ?
O2M C2M H2MC 109.5 . . ?
H2MA C2M H2MC 109.5 . . ?
H2MB C2M H2MC 109.5 . . ?
C2M O2M H2M 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.240
_diffrn_reflns_theta_full        28.49
_diffrn_measured_fraction_theta_full 0.240
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.093

#===END

data_NmetdabcoI10
_database_code_depnum_ccdc_archive 'CCDC 869509'
#TrackingRef '- structures.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
N-methyl-1,4-diazabicyclo[2.2.2]octanium iodide dimethanol cocrystal
;
_chemical_name_common            
;N-methyl-1,4-diazabicyclo(2.2.2)octanium iodide dimethanol
cocrystal
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H15 N2, 2(C H4 O), I'

_chemical_formula_sum            'C9 H23 I N2 O2'

_chemical_formula_weight         318.19

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/m'
_symmetry_space_group_name_Hall  '-P 2yb'

loop_

_symmetry_equiv_pos_as_xyz

'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   9.059(3)

_cell_length_b                   6.7868(17)

_cell_length_c                   10.543(4)

_cell_angle_alpha                90.00

_cell_angle_beta                 108.28(3)

_cell_angle_gamma                90.00

_cell_volume                     615.5(3)

_cell_formula_units_Z            2

_cell_measurement_temperature    296(2)

_cell_measurement_pressure       1000000

_cell_measurement_reflns_used    2279

_cell_measurement_theta_min      3.57

_cell_measurement_theta_max      26.85

_exptl_crystal_description       plate

_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.28

_exptl_crystal_size_mid          0.16

_exptl_crystal_size_min          0.10

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.717

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             320

_exptl_absorpt_coefficient_mu    2.584

_exptl_absorpt_correction_type   integration

_exptl_absorpt_correction_T_min  0.59

_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   
;
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Pozna\'n.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
;
Data were collected at room temperature and pressure of 1.0(5) GPa
(1000000 kPa) with the crystal obtained by the in-situ high-pressure
crystallization technique.
Pressure was determined by monitoring the shift of the ruby
R1-fluorescence line.
;
_diffrn_ambient_temperature      296(2)

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'multiwire proportional'

_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count 0

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        0

_diffrn_reflns_number            2279

_diffrn_reflns_av_R_equivalents  0.0394

_diffrn_reflns_av_sigmaI/netI    0.0159

_diffrn_reflns_limit_h_min       -5

_diffrn_reflns_limit_h_max       5

_diffrn_reflns_limit_k_min       -8

_diffrn_reflns_limit_k_max       8

_diffrn_reflns_limit_l_min       -9

_diffrn_reflns_limit_l_max       9

_diffrn_reflns_theta_min         3.57

_diffrn_reflns_theta_max         26.85

_reflns_number_total             221

_reflns_number_gt                210

_reflns_threshold_expression     >2sigma(I)

_refine_special_details          
;

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F^2^, conventional R-factors R are based

on F, with F set to zero for negative F^2^. The threshold expression of

F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F^2^ are statistically about twice as large as those based on F, and R-

factors based on ALL data will be even larger.
The DAC imposes severe restrictions on which reflections can be collected,
resulting in a low data:parameter ratio.

;

_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0338P)^2^+0.7968P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_number_reflns         221

_refine_ls_number_parameters     42

_refine_ls_number_restraints     2

_refine_ls_R_factor_all          0.0277

_refine_ls_R_factor_gt           0.0258

_refine_ls_wR_factor_ref         0.0617

_refine_ls_wR_factor_gt          0.0609

_refine_ls_goodness_of_fit_ref   1.178

_refine_ls_restrained_S_all      1.171

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000

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

I1 I 0.1708(3) 0.2500 0.28609(17) 0.054(6) Uani 1 2 d S . .
N1 N 0.153(3) 0.2500 -0.291(2) 0.029(2) Uiso 1 2 d S . .
C2 C 0.140(5) 0.2500 -0.159(3) 0.048(4) Uiso 1 2 d S . .
H2A H 0.0831 0.1342 -0.1468 0.058 Uiso 0.50 1 calc PR . .
H2B H 0.0831 0.3658 -0.1468 0.058 Uiso 0.50 1 calc PR . .
C3 C 0.307(7) 0.2500 -0.053(4) 0.038(7) Uiso 1 2 d S . .
H3A H 0.3200 0.3658 0.0035 0.045 Uiso 0.50 1 calc PR . .
H3B H 0.3200 0.1342 0.0035 0.045 Uiso 0.50 1 calc PR . .
N4 N 0.421(5) 0.2500 -0.118(3) 0.038(6) Uiso 1 2 d S . .
C5 C 0.411(3) 0.0730(9) -0.2058(18) 0.039(2) Uiso 1 1 d . . .
H5A H 0.4268 -0.0462 -0.1524 0.047 Uiso 1 1 calc R . .
H5B H 0.4896 0.0796 -0.2499 0.047 Uiso 1 1 calc R . .
C6 C 0.247(3) 0.0707(10) -0.3109(19) 0.0354(19) Uiso 1 1 d . . .
H6A H 0.2560 0.0740 -0.4000 0.042 Uiso 1 1 calc R . .
H6B H 0.1928 -0.0496 -0.3020 0.042 Uiso 1 1 calc R . .
C7 C 0.001(4) 0.2500 -0.397(3) 0.040(3) Uiso 1 2 d S . .
H7A H 0.0178 0.2500 -0.4829 0.048 Uiso 1 2 calc SR . .
H7B H -0.0564 0.3655 -0.3893 0.048 Uiso 0.50 1 calc PR . .
H7C H -0.0564 0.1345 -0.3893 0.048 Uiso 0.50 1 calc PR . .
O1M O 0.732(3) 0.2500 0.043(2) 0.059(5) Uiso 1 2 d SD . .
H1M H 0.6400 0.2500 -0.0025 0.071 Uiso 1 2 calc SR . .
C1M C 0.825(3) 0.2500 -0.042(3) 0.050(6) Uiso 1 2 d SD . .
H1MA H 0.7602 0.2500 -0.1334 0.060 Uiso 1 2 calc SR . .
H1MB H 0.8899 0.1345 -0.0251 0.060 Uiso 0.50 1 calc PR . .
H1MC H 0.8899 0.3655 -0.0251 0.060 Uiso 0.50 1 calc PR . .
O2M O 0.584(3) 0.2500 0.3946(19) 0.065(3) Uiso 1 2 d SD . .
H2M H 0.4922 0.2500 0.3490 0.078 Uiso 1 2 calc SR . .
C2M C 0.595(3) 0.2500 0.5310(19) 0.056(4) Uiso 1 2 d SD . .
H2MA H 0.4928 0.2500 0.5396 0.068 Uiso 1 2 calc SR . .
H2MB H 0.6503 0.3655 0.5732 0.068 Uiso 0.50 1 calc PR . .
H2MC H 0.6503 0.1345 0.5732 0.068 Uiso 0.50 1 calc PR . .

loop_

_atom_site_aniso_label

_atom_site_aniso_U_11

_atom_site_aniso_U_22

_atom_site_aniso_U_33

_atom_site_aniso_U_23

_atom_site_aniso_U_13

_atom_site_aniso_U_12

I1 0.064(9) 0.0409(5) 0.048(4) 0.000 0.005(5) 0.000

_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell esds are taken

into account individually in the estimation of esds in distances, angles

and torsion angles; correlations between esds in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell esds is used for estimating esds involving l.s. planes.

;

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

N1 C2 1.43(7) . ?
N1 C7 1.48(2) . ?
N1 C6 1.54(3) . ?
N1 C6 1.54(3) 4_565 ?
C2 C3 1.58(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N4 1.41(11) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N4 C5 1.50(3) . ?
N4 C5 1.50(3) 4_565 ?
C5 C6 1.550(19) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
O1M C1M 1.410(6) . ?
O1M H1M 0.8200 . ?
C1M H1MA 0.9600 . ?
C1M H1MB 0.9600 . ?
C1M H1MC 0.9600 . ?
O2M C2M 1.410(6) . ?
O2M H2M 0.8200 . ?
C2M H2MA 0.9600 . ?
C2M H2MB 0.9600 . ?
C2M H2MC 0.9600 . ?

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

C2 N1 C7 114(4) . . ?
C2 N1 C6 110.6(13) . . ?
C7 N1 C6 108.5(14) . . ?
C2 N1 C6 110.6(13) . 4_565 ?
C7 N1 C6 108.5(14) . 4_565 ?
C6 N1 C6 105(3) . 4_565 ?
N1 C2 C3 110(5) . . ?
N1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
N4 C3 C2 110(4) . . ?
N4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
N4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C3 N4 C5 113(3) . . ?
C3 N4 C5 113(3) . 4_565 ?
C5 N4 C5 107(3) . 4_565 ?
N4 C5 C6 108.0(19) . . ?
N4 C5 H5A 110.1 . . ?
C6 C5 H5A 110.1 . . ?
N4 C5 H5B 110.1 . . ?
C6 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
N1 C6 C5 109.9(11) . . ?
N1 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N1 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1M O1M H1M 109.5 . . ?
O1M C1M H1MA 109.5 . . ?
O1M C1M H1MB 109.5 . . ?
H1MA C1M H1MB 109.5 . . ?
O1M C1M H1MC 109.5 . . ?
H1MA C1M H1MC 109.5 . . ?
H1MB C1M H1MC 109.5 . . ?
C2M O2M H2M 109.5 . . ?
O2M C2M H2MA 109.5 . . ?
O2M C2M H2MB 109.5 . . ?
H2MA C2M H2MB 109.5 . . ?
O2M C2M H2MC 109.5 . . ?
H2MA C2M H2MC 109.5 . . ?
H2MB C2M H2MC 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.153

_diffrn_reflns_theta_full        26.85

_diffrn_measured_fraction_theta_full 0.153

_refine_diff_density_max         0.195

_refine_diff_density_min         -0.196

_refine_diff_density_rms         0.041

#===END

data_NmetdabcoI12
_database_code_depnum_ccdc_archive 'CCDC 869510'
#TrackingRef '- structures.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
N-methyl-1,4-diazabicyclo[2.2.2]octanium iodide dimethanol cocrystal
;
_chemical_name_common            
;N-methyl-1,4-diazabicyclo(2.2.2)octanium iodide dimethanol
cocrystal
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H15 N2, 2(C H4 O), I'

_chemical_formula_sum            'C9 H23 I N2 O2'

_chemical_formula_weight         318.19

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/m'
_symmetry_space_group_name_Hall  '-P 2yb'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   9.040(3)
_cell_length_b                   6.7590(9)
_cell_length_c                   10.516(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.45(3)
_cell_angle_gamma                90.00
_cell_volume                     609.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       1200000
_cell_measurement_reflns_used    2345
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      26.98

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    2.609
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_T_max  0.66
_exptl_absorpt_process_details   
;
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Pozna\'n.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
;
Data were collected at room temperature and pressure of 1.2(5) GPa
(1200000 kPa) with the crystal obtained by the in-situ high-pressure
crystallization technique.
Pressure was determined by monitoring the shift of the ruby
R1-fluorescence line.
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'

_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2345
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.59
_diffrn_reflns_theta_max         26.98
_reflns_number_total             226
_reflns_number_gt                218
_reflns_threshold_expression     >2sigma(I)

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
The DAC imposes severe restrictions on which reflections can be collected,
resulting in a low data:parameter ratio.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0739P)^2^+1.2296P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         226
_refine_ls_number_parameters     42
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1566
_refine_ls_wR_factor_gt          0.1544
_refine_ls_goodness_of_fit_ref   1.679
_refine_ls_restrained_S_all      1.644
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
I1 I 0.1705(7) 0.2500 0.2856(4) 0.046(13) Uani 1 2 d S . .
N1 N 0.155(5) 0.2500 -0.293(4) 0.028(5) Uiso 1 2 d SD . .
C2 C 0.130(7) 0.2500 -0.159(4) 0.043(8) Uiso 1 2 d SD . .
H2A H 0.0713 0.1335 -0.1492 0.051 Uiso 0.50 1 calc PR . .
H2B H 0.0713 0.3665 -0.1492 0.051 Uiso 0.50 1 calc PR . .
C3 C 0.299(9) 0.2500 -0.046(6) 0.06(2) Uiso 1 2 d SD . .
H3A H 0.3112 0.3664 0.0099 0.075 Uiso 0.50 1 calc PR . .
H3B H 0.3112 0.1336 0.0099 0.075 Uiso 0.50 1 calc PR . .
N4 N 0.419(7) 0.2500 -0.118(4) 0.014(8) Uiso 1 2 d SD . .
C5 C 0.411(6) 0.073(2) -0.206(4) 0.036(5) Uiso 1 1 d D . .
H5A H 0.4285 -0.0473 -0.1523 0.043 Uiso 1 1 calc R . .
H5B H 0.4891 0.0817 -0.2503 0.043 Uiso 1 1 calc R . .
C6 C 0.243(6) 0.070(2) -0.311(4) 0.033(5) Uiso 1 1 d D . .
H6A H 0.2514 0.0679 -0.4010 0.040 Uiso 1 1 calc R . .
H6B H 0.1885 -0.0488 -0.2995 0.040 Uiso 1 1 calc R . .
C7 C -0.003(9) 0.2500 -0.401(6) 0.020(5) Uiso 1 2 d S . .
H7A H 0.0113 0.2500 -0.4877 0.023 Uiso 1 2 calc SR . .
H7B H -0.0600 0.3660 -0.3918 0.023 Uiso 0.50 1 calc PR . .
H7C H -0.0600 0.1340 -0.3918 0.023 Uiso 0.50 1 calc PR . .
O1M O 0.739(7) 0.2500 0.041(5) 0.055(10) Uiso 1 2 d SD . .
H1M H 0.6460 0.2500 -0.0026 0.066 Uiso 1 2 calc SR . .
C1M C 0.828(7) 0.2500 -0.048(6) 0.054(15) Uiso 1 2 d SD . .
H1MA H 0.7591 0.2500 -0.1390 0.065 Uiso 1 2 calc SR . .
H1MB H 0.8924 0.1340 -0.0330 0.065 Uiso 0.50 1 calc PR . .
H1MC H 0.8924 0.3660 -0.0330 0.065 Uiso 0.50 1 calc PR . .
O2M O 0.593(7) 0.2500 0.395(4) 0.054(6) Uiso 1 2 d SD . .
H2M H 0.5010 0.2500 0.3482 0.064 Uiso 1 2 calc SR . .
C2M C 0.602(8) 0.2500 0.531(4) 0.049(9) Uiso 1 2 d SD . .
H2MA H 0.4983 0.2500 0.5383 0.059 Uiso 1 2 calc SR . .
H2MB H 0.6564 0.3660 0.5743 0.059 Uiso 0.50 1 calc PR . .
H2MC H 0.6564 0.1340 0.5743 0.059 Uiso 0.50 1 calc PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.049(19) 0.0369(11) 0.044(9) 0.000 0.005(12) 0.000

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N1 C6 1.50(3) 4_565 ?
N1 C6 1.50(3) . ?
N1 C7 1.52(4) . ?
N1 C2 1.50(3) . ?
C2 C3 1.61(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N4 1.50(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N4 C5 1.50(3) . ?
N4 C5 1.50(3) 4_565 ?
C5 C6 1.57(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
O1M C1M 1.410(5) . ?
O1M H1M 0.8200 . ?
C1M H1MA 0.9600 . ?
C1M H1MB 0.9600 . ?
C1M H1MC 0.9600 . ?
O2M C2M 1.410(5) . ?
O2M H2M 0.8200 . ?
C2M H2MA 0.9600 . ?
C2M H2MB 0.9600 . ?
C2M H2MC 0.9600 . ?

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
C6 N1 C6 109(4) 4_565 . ?
C6 N1 C7 109(3) 4_565 . ?
C6 N1 C7 109(3) . . ?
C6 N1 C2 111(2) 4_565 . ?
C6 N1 C2 111(2) . . ?
C7 N1 C2 108(5) . . ?
N1 C2 C3 107(4) . . ?
N1 C2 H2A 110.3 . . ?
C3 C2 H2A 110.3 . . ?
N1 C2 H2B 110.3 . . ?
C3 C2 H2B 110.3 . . ?
H2A C2 H2B 108.5 . . ?
N4 C3 C2 108(5) . . ?
N4 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
N4 C3 H3B 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.5 . . ?
C5 N4 C5 106(3) . 4_565 ?
C5 N4 C3 114(3) . . ?
C5 N4 C3 114(3) 4_565 . ?
N4 C5 C6 107(3) . . ?
N4 C5 H5A 110.2 . . ?
C6 C5 H5A 110.2 . . ?
N4 C5 H5B 110.2 . . ?
C6 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
N1 C6 C5 109(2) . . ?
N1 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N1 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1M O1M H1M 109.5 . . ?
O1M C1M H1MA 109.5 . . ?
O1M C1M H1MB 109.5 . . ?
H1MA C1M H1MB 109.5 . . ?
O1M C1M H1MC 109.5 . . ?
H1MA C1M H1MC 109.5 . . ?
H1MB C1M H1MC 109.5 . . ?
C2M O2M H2M 109.5 . . ?
O2M C2M H2MA 109.5 . . ?
O2M C2M H2MB 109.5 . . ?
H2MA C2M H2MB 109.5 . . ?
O2M C2M H2MC 109.5 . . ?
H2MA C2M H2MC 109.5 . . ?
H2MB C2M H2MC 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.156
_diffrn_reflns_theta_full        26.98
_diffrn_measured_fraction_theta_full 0.156
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.113

#===END

data_NmetdabcoI24
_database_code_depnum_ccdc_archive 'CCDC 869511'
#TrackingRef '- structures.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
N-methyl-1,4-diazabicyclo[2.2.2]octanium iodide dimethanol cocrystal
;
_chemical_name_common            
;N-methyl-1,4-diazabicyclo(2.2.2)octanium iodide dimethanol
cocrystal
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H15 N2, 2(C H4 O), I'

_chemical_formula_sum            'C9 H23 I N2 O2'

_chemical_formula_weight         318.19

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Mercury (2008)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/m'
_symmetry_space_group_name_Hall  '-P 2yb'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   8.879(3)
_cell_length_b                   6.6161(9)
_cell_length_c                   10.328(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.81(3)
_cell_angle_gamma                90.00
_cell_volume                     574.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_pressure       2400000
_cell_measurement_reflns_used    2509
_cell_measurement_theta_min      3.67
_cell_measurement_theta_max      28.17

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    2.769
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.41
_exptl_absorpt_correction_T_max  0.70
_exptl_absorpt_process_details   
;
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Pozna\'n.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_special_details           
;
Data were collected at room temperature and pressure of 2.4(5) GPa
(2400000 kPa) with the crystal obtained by the in-situ high-pressure
crystallization technique.
Pressure was determined by monitoring the shift of the ruby
R1-fluorescence line.
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'

_diffrn_measurement_method       
;
HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2509
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.67
_diffrn_reflns_theta_max         28.17
_reflns_number_total             241
_reflns_number_gt                240
_reflns_threshold_expression     >2sigma(I)

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+5.5037P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         241
_refine_ls_number_parameters     42
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.0884
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.394
_refine_ls_restrained_S_all      1.388
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
I1 I 0.1710(5) 0.2500 0.2833(3) 0.032(6) Uani 1 2 d S . .
N1 N 0.153(5) 0.2500 -0.298(3) 0.012(4) Uiso 1 2 d S . .
C2 C 0.128(8) 0.2500 -0.158(5) 0.026(5) Uiso 1 2 d S . .
H2A H 0.0687 0.3691 -0.1480 0.031 Uiso 0.50 1 calc PR . .
H2B H 0.0687 0.1309 -0.1480 0.031 Uiso 0.50 1 calc PR . .
C3 C 0.300(9) 0.2500 -0.047(6) 0.026(10) Uiso 1 2 d S . .
H3A H 0.3128 0.3687 0.0107 0.031 Uiso 0.50 1 calc PR . .
H3B H 0.3128 0.1313 0.0107 0.031 Uiso 0.50 1 calc PR . .
N4 N 0.430(8) 0.2500 -0.117(5) 0.020(8) Uiso 1 2 d S . .
C5 C 0.419(5) 0.0682(18) -0.205(3) 0.028(4) Uiso 1 1 d . . .
H5B H 0.4966 0.0756 -0.2523 0.034 Uiso 1 1 calc R . .
H5A H 0.4381 -0.0534 -0.1495 0.034 Uiso 1 1 calc R . .
C6 C 0.243(5) 0.0651(19) -0.312(3) 0.026(4) Uiso 1 1 d . . .
H6A H 0.1878 -0.0540 -0.2965 0.031 Uiso 1 1 calc R . .
H6B H 0.2492 0.0576 -0.4039 0.031 Uiso 1 1 calc R . .
C7 C -0.004(6) 0.2500 -0.405(4) 0.020(5) Uiso 1 2 d S . .
H7A H 0.0090 0.2500 -0.4932 0.024 Uiso 1 2 calc SR . .
H7B H -0.0619 0.3685 -0.3948 0.024 Uiso 0.50 1 calc PR . .
H7C H -0.0619 0.1315 -0.3948 0.024 Uiso 0.50 1 calc PR . .
O1M O 0.743(5) 0.2500 0.047(3) 0.042(6) Uiso 1 2 d SD . .
H1M H 0.6474 0.2500 0.0036 0.050 Uiso 1 2 calc SR . .
C1M C 0.830(6) 0.2500 -0.045(4) 0.038(9) Uiso 1 2 d SD . .
H1MA H 0.7582 0.2500 -0.1376 0.045 Uiso 1 2 calc SR . .
H1MB H 0.8960 0.1315 -0.0308 0.045 Uiso 0.50 1 calc PR . .
H1MC H 0.8960 0.3685 -0.0308 0.045 Uiso 0.50 1 calc PR . .
O2M O 0.594(5) 0.2500 0.400(3) 0.046(5) Uiso 1 2 d SD . .
H2M H 0.5024 0.2500 0.3475 0.055 Uiso 1 2 calc SR . .
C2M C 0.594(5) 0.2500 0.536(3) 0.031(6) Uiso 1 2 d SD . .
H2MA H 0.4866 0.2500 0.5371 0.037 Uiso 1 2 calc SR . .
H2MB H 0.6481 0.3685 0.5819 0.037 Uiso 0.50 1 calc PR . .
H2MC H 0.6481 0.1315 0.5819 0.037 Uiso 0.50 1 calc PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.035(9) 0.0277(7) 0.030(5) 0.000 0.007(6) 0.000

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N1 C7 1.47(3) . ?
N1 C2 1.54(9) . ?
N1 C6 1.49(4) 4_565 ?
N1 C6 1.49(4) . ?
C2 C3 1.59(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N4 1.54(15) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N4 C5 1.49(4) . ?
N4 C5 1.49(4) 4_565 ?
C5 C6 1.59(3) . ?
C5 H5B 0.9700 . ?
C5 H5A 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
O1M C1M 1.41(5) . ?
O1M H1M 0.8200 . ?
C1M H1MA 0.9600 . ?
C1M H1MB 0.9600 . ?
C1M H1MC 0.9600 . ?
O2M C2M 1.410(5) . ?
O2M H2M 0.8200 . ?
C2M H2MA 0.9600 . ?
C2M H2MB 0.9600 . ?
C2M H2MC 0.9600 . ?

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
C7 N1 C2 108(5) . . ?
C7 N1 C6 109.9(17) . 4_565 ?
C2 N1 C6 110(2) . 4_565 ?
C7 N1 C6 109.9(17) . . ?
C2 N1 C6 110(2) . . ?
C6 N1 C6 110(5) 4_565 . ?
C3 C2 N1 106(7) . . ?
C3 C2 H2A 110.5 . . ?
N1 C2 H2A 110.5 . . ?
C3 C2 H2B 110.5 . . ?
N1 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
N4 C3 C2 110(5) . . ?
N4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
N4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C3 N4 C5 112(4) . . ?
C3 N4 C5 112(4) . 4_565 ?
C5 N4 C5 108(4) . 4_565 ?
C6 C5 N4 107(3) . . ?
C6 C5 H5B 110.3 . . ?
N4 C5 H5B 110.3 . . ?
C6 C5 H5A 110.3 . . ?
N4 C5 H5A 110.3 . . ?
H5B C5 H5A 108.6 . . ?
C5 C6 N1 111.0(15) . . ?
C5 C6 H6A 109.4 . . ?
N1 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
N1 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1M O1M H1M 109.5 . . ?
O1M C1M H1MA 109.5 . . ?
O1M C1M H1MB 109.5 . . ?
H1MA C1M H1MB 109.5 . . ?
O1M C1M H1MC 109.5 . . ?
H1MA C1M H1MC 109.5 . . ?
H1MB C1M H1MC 109.5 . . ?
C2M O2M H2M 109.5 . . ?
O2M C2M H2MA 109.5 . . ?
O2M C2M H2MB 109.5 . . ?
H2MA C2M H2MB 109.5 . . ?
O2M C2M H2MC 109.5 . . ?
H2MA C2M H2MC 109.5 . . ?
H2MB C2M H2MC 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.157
_diffrn_reflns_theta_full        28.17
_diffrn_measured_fraction_theta_full 0.157
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.077

#===END