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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
  'N-methylglycine ammonium nitrate'
;
_chemical_name_common     'sarcosine ammonium nitrate'
_chemical_formula_moiety     'C3 H7 N O2, H4 N+, N O3 -'
_chemical_formula_sum     'C3 H11 N3 O5'
_chemical_formula_iupac     'C3 H7 N O2, H4 N+, N O3 -'
_chemical_formula_weight     169.15
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     P21/c
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     5.7208(9)
_cell_length_b     7.9144(8)
_cell_length_c     17.447(2)
_cell_angle_alpha     90.00
_cell_angle_beta     101.682(13)
_cell_angle_gamma     90.00
_cell_volume     773.58(17)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     6.59
_cell_measurement_theta_max     17.29
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.43
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.39
_exptl_crystal_density_diffrn     1.452
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     360
_exptl_absorpt_coefficient_mu     0.136
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
  ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71074
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf--Nonius CAD-4 diffractometer'
_diffrn_measurement_method     'profile data from ω-2θ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     2819
_diffrn_reflns_av_R_equivalents     0.0367
_diffrn_reflns_av_sigmaI/netI     0.0448
_diffrn_reflns_theta_min     2.84
_diffrn_reflns_theta_max     25.46
_diffrn_reflns_theta_full     25.46
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     6
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     7200
_diffrn_standards_decay_%     0.3
_refine_special_details
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F², conventional R-factors R are based
  on F, with F set to zero for negative F². The threshold expression of
  F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
  not relevant to the choice of reflections for refinement.  R-factors based
  on F² are statistically about twice as large as those based on F, and R-
  factors based on ALL data will be even larger.
;
_reflns_number_total     1423
_reflns_number_gt     901
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0901
_refine_ls_R_factor_gt     0.0413
_refine_ls_wR_factor_gt     0.1102
_refine_ls_wR_factor_ref     0.1298
_refine_ls_goodness_of_fit_ref     0.982
_refine_ls_restrained_S_all     0.980
_refine_ls_number_reflns     1423
_refine_ls_number_parameters     121
_refine_ls_number_restraints     10
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0885P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.186
_refine_diff_density_min     -0.255
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software'
_computing_data_reduction     'PLATON (Spek, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEPII (Johnson, 1976)'
_computing_publication_material     'SHELXL97'
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    O1 0.9102(3) 0.23951(19) 0.13575(9) 0.0392(4) Uani d . 1 . . O
    O2 0.7208(3) 0.1325(2) 0.02244(9) 0.0442(5) Uani d . 1 . . O
    C1 0.7251(4) 0.1963(2) 0.08725(13) 0.0306(5) Uani d . 1 . . C
    N1 0.2800(3) 0.1830(2) 0.05347(10) 0.0332(5) Uani d . 1 . . N
    H1A 0.154(2) 0.1719(3) 0.0763(4) 0.040 Uiso calc R 1 . . H
    H1B 0.3046(5) 0.0830(19) 0.0326(4) 0.040 Uiso calc R 1 . . H
    C2 0.4902(3) 0.2253(3) 0.11365(13) 0.0325(5) Uani d . 1 . . C
    H2A 0.4887(3) 0.1597(11) 0.1582(8) 0.039 Uiso calc R 1 . . H
    H2B 0.4808(4) 0.3387(19) 0.1277(3) 0.039 Uiso calc R 1 . . H
    C3 0.2213(4) 0.3082(4) -0.01002(16) 0.0563(8) Uani d . 1 . . C
    H3A 0.195(4) 0.418(2) 0.0119(4) 0.084 Uiso calc R 1 . . H
    H3B 0.078(3) 0.2733(14) -0.0464(9) 0.084 Uiso calc R 1 . . H
    H3C 0.353(3) 0.3163(19) -0.0374(9) 0.084 Uiso calc R 1 . . H
    N3 0.0319(3) 0.0545(2) 0.28475(11) 0.0389(5) Uani d D 1 . . N
    H4 0.066(4) -0.055(3) 0.3039(15) 0.083(10) Uiso d D 1 . . H
    H5 -0.008(5) 0.051(4) 0.2295(11) 0.082(10) Uiso d D 1 . . H
    H6 -0.097(5) 0.098(4) 0.3025(17) 0.109(14) Uiso d D 1 . . H
    H7 0.173(4) 0.118(4) 0.2998(19) 0.128(16) Uiso d D 1 . . H
    O3 0.3624(3) 0.3477(2) 0.31995(13) 0.0661(6) Uani d . 1 . . O
    O4 0.5828(3) 0.1282(2) 0.33614(14) 0.0686(7) Uani d . 1 . . O
    O5 0.7443(3) 0.3697(2) 0.32930(13) 0.0610(6) Uani d . 1 . . O
    N2 0.5642(3) 0.2840(2) 0.32817(11) 0.0399(5) Uani d . 1 . . N
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0262(8) 0.0469(9) 0.0442(9) -0.0024(7) 0.0066(7) -0.0111(7)
    O2 0.0351(9) 0.0528(10) 0.0484(10) -0.0038(7) 0.0172(7) -0.0215(8)
    C1 0.0315(12) 0.0232(10) 0.0389(12) -0.0003(8) 0.0113(9) -0.0040(9)
    N1 0.0251(9) 0.0345(9) 0.0428(11) -0.0015(7) 0.0139(8) -0.0078(8)
    C2 0.0294(12) 0.0322(11) 0.0378(11) -0.0012(9) 0.0116(9) -0.0058(9)
    C3 0.0394(15) 0.0800(19) 0.0498(15) 0.0097(13) 0.0100(11) 0.0121(14)
    N3 0.0380(12) 0.0382(11) 0.0406(12) 0.0023(9) 0.0079(9) 0.0023(9)
    O3 0.0413(11) 0.0556(11) 0.1012(16) 0.0079(9) 0.0136(10) 0.0064(11)
    O4 0.0630(13) 0.0314(10) 0.1206(19) 0.0006(8) 0.0406(12) -0.0009(10)
    O5 0.0514(12) 0.0541(11) 0.0840(14) -0.0157(9) 0.0294(10) 0.0037(10)
    N2 0.0408(12) 0.0384(11) 0.0440(11) -0.0015(9) 0.0166(9) 0.0009(9)
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C1 . 1.261(3) yes
    O2 C1 . 1.234(3) yes
    C1 C2 . 1.524(3) ?
    N1 C2 . 1.466(3) ?
    N1 C3 . 1.474(3) ?
    N1 H1A . 0.8942 ?
    N1 H1B . 0.8942 ?
    C2 H2A . 0.9351 ?
    C2 H2B . 0.9351 ?
    C3 H3A . 0.9710 ?
    C3 H3B . 0.9710 ?
    C3 H3C . 0.9710 ?
    N3 H4 . 0.94(2) ?
    N3 H5 . 0.945(19) ?
    N3 H6 . 0.92(2) ?
    N3 H7 . 0.94(2) ?
    O3 N2 . 1.241(3) yes
    O4 N2 . 1.243(3) yes
    O5 N2 . 1.231(2) yes
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 C1 O1 . . 125.72(19) ?
    O2 C1 C2 . . 118.90(19) ?
    O1 C1 C2 . . 115.37(19) ?
    C2 N1 C3 . . 114.45(19) ?
    C2 N1 H1A . . 108.6 ?
    C3 N1 H1A . . 108.6 ?
    C2 N1 H1B . . 108.6 ?
    C3 N1 H1B . . 108.6 ?
    H1A N1 H1B . . 107.6 ?
    N1 C2 C1 . . 113.26(18) ?
    N1 C2 H2A . . 108.9 ?
    C1 C2 H2A . . 108.9 ?
    N1 C2 H2B . . 108.9 ?
    C1 C2 H2B . . 108.9 ?
    H2A C2 H2B . . 107.7 ?
    N1 C3 H3A . . 109.5 ?
    N1 C3 H3B . . 109.5 ?
    H3A C3 H3B . . 109.5 ?
    N1 C3 H3C . . 109.5 ?
    H3A C3 H3C . . 109.5 ?
    H3B C3 H3C . . 109.5 ?
    H4 N3 H5 . . 108.8(19) ?
    H4 N3 H6 . . 110.5(19) ?
    H5 N3 H6 . . 108.1(19) ?
    H4 N3 H7 . . 106.9(18) ?
    H5 N3 H7 . . 109(2) ?
    H6 N3 H7 . . 114(2) ?
    O5 N2 O3 . . 122.30(19) ?
    O5 N2 O4 . . 119.5(2) ?
    O3 N2 O4 . . 118.2(2) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C3 N1 C2 C1 . . . . -75.5(2) yes
    O2 C1 C2 N1 . . . . -4.4(3) yes
    O1 C1 C2 N1 . . . . 176.4(2) yes
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1A O1 1_455 0.89 1.97 2.822(2) 158
    N1 H1A O2 1_455 0.89 2.49 3.160(2) 132
    N1 H1B O2 3_655 0.89 1.95 2.826(2) 167
    N3 H4 O1 2_645 0.94(2) 1.92(2) 2.839(2) 164(2)
    N3 H5 O1 1_455 0.945(19) 2.20(2) 2.942(2) 135(2)
    N3 H5 O5 2_645 0.945(19) 2.45(3) 2.961(3) 114(2)
    N3 H5 O3 2_545 0.945(19) 2.59(3) 3.072(3) 112(2)
    N3 H6 O4 1_455 0.92(2) 2.05(2) 2.946(3) 164(3)
    N3 H6 O5 1_455 0.92(2) 2.42(3) 3.171(3) 139(3)
    N3 H6 N2 1_455 0.92(2) 2.55(2) 3.443(3) 164(3)
    N3 H7 O3 . 0.94(2) 2.11(2) 2.977(3) 153(3)
    N3 H7 O4 . 0.94(2) 2.31(2) 3.151(3) 149(3)
    N3 H7 N2 . 0.94(2) 2.56(2) 3.494(3) 175(3)
data_global
_journal_date_recd_electronic     2004-12-13
_journal_date_accepted     2005-04-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      6
_journal_page_first     o1631
_journal_page_last     o1633
_journal_paper_category     EO
_publ_contact_author_name     'M. Ramos Silva'
_publ_contact_author_address
;
      CEMDRX, Departamento de Física
      Faculdade de Ciências e Tecnologia
      Universidade de Coimbra
      P-3004-516 Coimbra
      Portugal
;
_publ_contact_author_email     manuela@pollux.fis.uc.pt
_publ_contact_author_fax     351-239-829158
_publ_contact_author_phone     351-239-410600
_publ_section_title
;
Sarcosine ammonium nitrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Rodrigues, V. H.' .
;
      CEMDRX, Departamento de Física
      Faculdade de Ciências e Tecnologia
      Universidade de Coimbra
      P-3004-516 Coimbra
      Portugal
;
    'Ramos Silva, M.' 'Correspondence author'
;
      CEMDRX, Departamento de Física
      Faculdade de Ciências e Tecnologia
      Universidade de Coimbra
      P-3004-516 Coimbra
      Portugal
;
    'Matos Beja, A.' .
;
      CEMDRX, Departamento de Física
      Faculdade de Ciências e Tecnologia
      Universidade de Coimbra
      P-3004-516 Coimbra
      Portugal
;
    'Paixão, J. A.' .
;
      CEMDRX, Departamento de Física
      Faculdade de Ciências e Tecnologia
      Universidade de Coimbra
      P-3004-516 Coimbra
      Portugal
;
    'Costa, M.M.R.R.' .
;
      CEMDRX, Departamento de Física
      Faculdade de Ciências e Tecnologia
      Universidade de Coimbra
      P-3004-516 Coimbra
      Portugal
;
