#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:04:12 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179650 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/03/4510364.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_4510364
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 H2 N3 O3, C4 H12 N'
_chemical_formula_sum            'C7 H14 N4 O3'
_chemical_formula_weight         202.22
_chemical_name_common            (Me4N)(ccnom)
_chemical_name_systematic
;
 Tetramethylammonium carbamoylcyanonitrosomethanide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.899(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4023(3)
_cell_length_b                   17.2639(8)
_cell_length_c                   8.3753(4)
_cell_measurement_reflns_used    8837
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.01
_cell_volume                     1064.63(8)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8837
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_correction_T_min  0.9804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       shard
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2440
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0362
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                2020
_reflns_number_total             2440
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            6-(Me4N)(ccnom).CIF
_cod_data_source_block           (Me4N)(ccnom).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/n
_cod_database_code               4510364
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
N4 N 0.46491(13) 0.33709(6) 0.80141(12) 0.0316(2) Uani 1 1 d .
C7 C 0.49632(17) 0.41853(7) 0.74938(16) 0.0357(3) Uani 1 1 d .
H7A H 0.3953 0.4349 0.6719 0.054 Uiso 1 1 calc R
H7B H 0.6100 0.4211 0.6992 0.054 Uiso 1 1 calc R
H7C H 0.5041 0.4529 0.8430 0.054 Uiso 1 1 calc R
C6 C 0.45152(18) 0.28545(8) 0.65880(16) 0.0391(3) Uani 1 1 d .
H6A H 0.3512 0.3027 0.5814 0.059 Uiso 1 1 calc R
H6B H 0.4290 0.2322 0.6921 0.059 Uiso 1 1 calc R
H6C H 0.5655 0.2874 0.6088 0.059 Uiso 1 1 calc R
C5 C 0.6212(2) 0.31172(10) 0.91623(19) 0.0538(4) Uani 1 1 d .
H5A H 0.7327 0.3125 0.8625 0.081 Uiso 1 1 calc R
H5B H 0.5992 0.2590 0.9532 0.081 Uiso 1 1 calc R
H5C H 0.6343 0.3470 1.0084 0.081 Uiso 1 1 calc R
C4 C 0.2927(2) 0.33330(10) 0.8792(2) 0.0560(4) Uani 1 1 d .
H4A H 0.2719 0.2799 0.9128 0.084 Uiso 1 1 calc R
H4B H 0.1912 0.3501 0.8026 0.084 Uiso 1 1 calc R
H4C H 0.3019 0.3674 0.9733 0.084 Uiso 1 1 calc R
N1 N 0.43819(13) 0.11479(6) 0.97432(12) 0.0299(2) Uani 1 1 d .
C1 C 0.33892(14) 0.08866(6) 0.83907(13) 0.0258(2) Uani 1 1 d .
C2 C 0.14882(15) 0.10135(7) 0.83003(14) 0.0309(3) Uani 1 1 d .
C3 C 0.41002(15) 0.05012(6) 0.70239(14) 0.0266(2) Uani 1 1 d .
N2 N -0.00542(15) 0.11092(8) 0.81753(15) 0.0496(3) Uani 1 1 d .
O4 O 0.60753(11) 0.10531(6) 0.99339(12) 0.0468(3) Uani 1 1 d .
O2 O 0.29820(11) 0.02911(5) 0.58965(10) 0.0351(2) Uani 1 1 d .
N3 N 0.58816(13) 0.04071(7) 0.70051(13) 0.0380(3) Uani 1 1 d .
H3A H 0.6310 0.0189 0.6172 0.046 Uiso 1 1 calc R
H3B H 0.6632 0.0563 0.7825 0.046 Uiso 1 1 calc R
O3 O 0.35986(12) 0.15066(6) 1.07930(11) 0.0403(2) Uani 1 1 d .
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
N4 0.0291(5) 0.0343(5) 0.0306(5) 0.0062(4) -0.0001(4) -0.0009(4)
C7 0.0365(7) 0.0297(6) 0.0410(7) 0.0019(5) 0.0050(5) -0.0015(5)
C6 0.0433(7) 0.0330(6) 0.0399(7) 0.0004(5) -0.0018(6) -0.0071(5)
C5 0.0518(9) 0.0554(9) 0.0490(8) 0.0152(7) -0.0206(7) -0.0047(7)
C4 0.0505(9) 0.0604(9) 0.0616(10) 0.0163(8) 0.0269(8) 0.0004(7)
N1 0.0236(5) 0.0350(5) 0.0312(5) -0.0054(4) 0.0034(4) -0.0033(4)
C1 0.0200(5) 0.0271(5) 0.0302(6) -0.0030(4) 0.0026(4) -0.0016(4)
C2 0.0256(6) 0.0392(6) 0.0282(6) -0.0094(5) 0.0041(4) -0.0014(5)
C3 0.0227(5) 0.0267(5) 0.0306(6) -0.0030(4) 0.0037(4) -0.0013(4)
N2 0.0260(6) 0.0783(9) 0.0445(7) -0.0217(6) 0.0030(5) 0.0038(5)
O4 0.0201(4) 0.0744(7) 0.0445(5) -0.0186(5) -0.0033(4) 0.0002(4)
O2 0.0235(4) 0.0480(5) 0.0337(4) -0.0130(4) 0.0028(3) -0.0010(4)
N3 0.0215(5) 0.0540(7) 0.0383(6) -0.0159(5) 0.0030(4) 0.0027(4)
O3 0.0333(5) 0.0523(6) 0.0359(5) -0.0169(4) 0.0064(4) -0.0027(4)
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
C6 N4 C4 109.61(11)
C6 N4 C5 108.99(11)
C4 N4 C5 110.27(12)
C6 N4 C7 109.21(9)
C4 N4 C7 109.48(10)
C5 N4 C7 109.26(10)
O4 N1 O3 119.85(10)
O4 N1 C1 120.52(10)
O3 N1 C1 119.60(9)
N1 C1 C2 116.15(10)
N1 C1 C3 126.35(10)
C2 C1 C3 117.50(10)
N2 C2 C1 177.76(13)
O2 C3 N3 122.57(10)
O2 C3 C1 117.40(10)
N3 C3 C1 120.00(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N4 C6 1.4855(16)
N4 C4 1.4913(17)
N4 C5 1.4920(17)
N4 C7 1.4972(15)
N1 O4 1.2579(13)
N1 O3 1.2639(12)
N1 C1 1.3622(15)
C1 C2 1.4185(15)
C1 C3 1.4676(15)
C2 N2 1.1477(16)
C3 O2 1.2440(14)
C3 N3 1.3304(14)
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
N3 H3A O2 0.88 2.04 2.9131(13) 173.4 3_656
N3 H3B O4 0.88 2.04 2.6850(14) 129.5 .
N3 H3B N2 0.88 2.62 3.2977(15) 135.0 1_655
