#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:04:12 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179650 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/03/4510362.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_4510362
loop_
_publ_author_name
'Chesman, Anthony S. R.'
'Hodgson, Jennifer L.'
'Izgorodina, Ekaterina I.'
'Urbatsch, Aron'
'Turner, David R.'
'Deacon, Glen B.'
'Batten, Stuart R.'
_publ_section_title
;
 Anion--Anion Interactions in the Crystal Packing of Functionalized
 Methanide Anions: An Experimental and Computational Study
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1922
_journal_paper_doi               10.1021/cg500051m
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C3 N3 O2, C4 H12 N'
_chemical_formula_sum            'C7 H12 N4 O2'
_chemical_formula_weight         184.21
_chemical_name_common            (Me4N)(dcnom)
_chemical_name_systematic
;
 Tetramethylammonium dicyanonitromethanide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 109.555(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.5852(12)
_cell_length_b                   15.6154(19)
_cell_length_c                   11.3954(11)
_cell_measurement_reflns_used    15447
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.63
_cell_volume                     1942.6(4)
_computing_cell_refinement       'Bruker SMART (Bruker)'
_computing_data_collection       'Bruker SMART (Bruker)'
_computing_data_reduction        'Bruker SAINT (Bruker)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker X8 Apex II CCD'
_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  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15447
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.63
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_correction_T_min  0.9812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1273
_reflns_number_gt                3251
_reflns_number_total             4453
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            2-(Me4N)(dcnom).CIF
_cod_data_source_block           (Me4N)(dcnom).CIF
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/automatic-downloads/current/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      P21/c
_cod_database_code               4510362
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N7 N 0.10602(10) 0.18383(7) 0.62407(10) 0.0312(3) Uani 1 1 d .
N8 N 0.38881(10) 0.83996(7) 0.84633(10) 0.0303(3) Uani 1 1 d .
N4 N 0.29916(10) 0.54398(8) 0.96771(10) 0.0375(3) Uani 1 1 d .
N1 N 0.12905(10) 0.60848(8) 0.59807(11) 0.0358(3) Uani 1 1 d .
N6 N 0.33245(13) 0.34125(9) 0.86679(13) 0.0472(3) Uani 1 1 d .
N2 N 0.27833(12) 0.43334(9) 0.53707(13) 0.0479(3) Uani 1 1 d .
N3 N 0.00090(14) 0.45343(10) 0.72816(13) 0.0526(4) Uani 1 1 d .
N5 N 0.48161(14) 0.58683(10) 0.79021(13) 0.0535(4) Uani 1 1 d .
C4 C 0.35584(12) 0.50231(9) 0.89581(12) 0.0313(3) Uani 1 1 d .
C3 C 0.06060(13) 0.48482(9) 0.67790(13) 0.0355(3) Uani 1 1 d .
C1 C 0.13486(11) 0.52210(9) 0.61618(12) 0.0308(3) Uani 1 1 d .
C5 C 0.42459(13) 0.55011(10) 0.83818(13) 0.0368(3) Uani 1 1 d .
C6 C 0.34186(12) 0.41358(10) 0.88141(12) 0.0334(3) Uani 1 1 d .
C2 C 0.21415(12) 0.47414(10) 0.57219(12) 0.0347(3) Uani 1 1 d .
O2 O 0.05665(10) 0.65128(7) 0.63439(11) 0.0510(3) Uani 1 1 d .
O1 O 0.19534(10) 0.64269(7) 0.54500(10) 0.0495(3) Uani 1 1 d .
O4 O 0.23882(10) 0.50192(7) 1.01999(10) 0.0470(3) Uani 1 1 d .
O3 O 0.31018(12) 0.62299(8) 0.97972(11) 0.0579(3) Uani 1 1 d .
C11 C 0.46848(15) 0.81141(12) 0.77607(15) 0.0493(4) Uani 1 1 d .
H11A H 0.4304 0.8264 0.6880 0.074 Uiso 1 1 calc R
H11B H 0.4795 0.7492 0.7842 0.074 Uiso 1 1 calc R
H11C H 0.5484 0.8397 0.8095 0.074 Uiso 1 1 calc R
C14 C 0.44679(14) 0.81744(12) 0.98009(14) 0.0482(4) Uani 1 1 d .
H14A H 0.5260 0.8466 1.0137 0.072 Uiso 1 1 calc R
H14B H 0.4592 0.7554 0.9883 0.072 Uiso 1 1 calc R
H14C H 0.3933 0.8356 1.0264 0.072 Uiso 1 1 calc R
C12 C 0.26764(14) 0.79704(15) 0.79507(17) 0.0609(5) Uani 1 1 d .
H12A H 0.2125 0.8191 0.8371 0.091 Uiso 1 1 calc R
H12B H 0.2779 0.7351 0.8088 0.091 Uiso 1 1 calc R
H12C H 0.2326 0.8086 0.7056 0.091 Uiso 1 1 calc R
C13 C 0.3732(2) 0.93297(11) 0.83372(17) 0.0596(5) Uani 1 1 d .
H13A H 0.4536 0.9608 0.8639 0.089 Uiso 1 1 calc R
H13B H 0.3233 0.9527 0.8829 0.089 Uiso 1 1 calc R
H13C H 0.3322 0.9476 0.7459 0.089 Uiso 1 1 calc R
C9 C 0.04452(17) 0.25151(13) 0.67204(16) 0.0599(5) Uani 1 1 d .
H9A H -0.0062 0.2865 0.6025 0.090 Uiso 1 1 calc R
H9B H 0.1063 0.2878 0.7308 0.090 Uiso 1 1 calc R
H9C H -0.0073 0.2251 0.7146 0.090 Uiso 1 1 calc R
C7 C 0.0145(2) 0.12913(14) 0.5358(2) 0.0877(8) Uani 1 1 d .
H7A H 0.0561 0.0848 0.5040 0.132 Uiso 1 1 calc R
H7B H -0.0367 0.1640 0.4663 0.132 Uiso 1 1 calc R
H7C H -0.0370 0.1021 0.5781 0.132 Uiso 1 1 calc R
C10 C 0.18481(16) 0.13240(11) 0.73032(16) 0.0513(4) Uani 1 1 d .
H10A H 0.1337 0.1041 0.7721 0.077 Uiso 1 1 calc R
H10B H 0.2439 0.1701 0.7895 0.077 Uiso 1 1 calc R
H10C H 0.2288 0.0890 0.6996 0.077 Uiso 1 1 calc R
C8 C 0.18362(17) 0.22510(14) 0.56156(18) 0.0647(5) Uani 1 1 d .
H8A H 0.2250 0.1811 0.5288 0.097 Uiso 1 1 calc R
H8B H 0.2449 0.2611 0.6213 0.097 Uiso 1 1 calc R
H8C H 0.1327 0.2606 0.4928 0.097 Uiso 1 1 calc R
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
C7 N7 C8 109.99(16)
C7 N7 C9 110.06(15)
C8 N7 C9 108.33(14)
C7 N7 C10 110.50(14)
C8 N7 C10 108.89(13)
C9 N7 C10 109.04(12)
C13 N8 C11 108.97(13)
C13 N8 C12 109.80(14)
C11 N8 C12 109.25(13)
C13 N8 C14 109.49(13)
C11 N8 C14 109.51(12)
C12 N8 C14 109.82(12)
O3 N4 O4 121.58(12)
O3 N4 C4 118.93(13)
O4 N4 C4 119.49(13)
O2 N1 O1 121.60(13)
O2 N1 C1 119.01(12)
O1 N1 C1 119.39(12)
N4 C4 C6 118.67(12)
N4 C4 C5 119.11(13)
C6 C4 C5 122.22(13)
N3 C3 C1 179.08(16)
N1 C1 C2 118.67(12)
N1 C1 C3 118.55(12)
C2 C1 C3 122.78(13)
N5 C5 C4 178.02(17)
N6 C6 C4 177.69(15)
N2 C2 C1 178.58(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N7 C7 1.467(2)
N7 C8 1.470(2)
N7 C9 1.4778(19)
N7 C10 1.4848(18)
N8 C13 1.465(2)
N8 C11 1.4787(18)
N8 C12 1.4873(19)
N8 C14 1.4875(18)
N4 O3 1.2433(17)
N4 O4 1.2464(16)
N4 C4 1.3733(18)
N1 O2 1.2465(15)
N1 O1 1.2458(15)
N1 C1 1.3628(19)
N6 C6 1.1415(19)
N2 C2 1.1481(18)
N3 C3 1.1453(19)
N5 C5 1.1426(19)
C4 C6 1.398(2)
C4 C5 1.405(2)
C3 C1 1.407(2)
C1 C2 1.4015(19)
