#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/34/2223449.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2223449
loop_
_publ_author_name
'Kant, Rajni'
'Kohli, Sabeta'
'Sarmal, Lovely'
'Narayana, B.'
'Samshuddin, S.'
_publ_section_title
;
 4-(2-Chloroethyl)morpholinium picrate
;
_journal_coeditor_code           JH2096
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2435
_journal_paper_doi               10.1107/S1600536809035405
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C6 H13 Cl N O +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C12 H15 Cl N4 O8'
_chemical_formula_weight         378.72
_chemical_name_systematic
;
4-(2-Chloroethyl)morpholinium picrate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                93.954(5)
_cell_angle_beta                 95.284(5)
_cell_angle_gamma                90.376(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2063(4)
_cell_length_b                   9.3075(5)
_cell_length_c                   10.2896(6)
_cell_measurement_reflns_used    3665
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.3
_cell_measurement_theta_min      3.3
_cell_volume                     780.65(7)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows(Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device       'X-ray diffractometer with CCD camera'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8478
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         32.3
_diffrn_reflns_theta_min         3.3
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.847
_refine_diff_density_min         -0.605
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0877P)²+0.2886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1792
_reflns_number_gt                3665
_reflns_number_total             4960
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2096.cif
_cod_data_source_block           I
_cod_database_code               2223449
_cod_database_fobs_code          2223449
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
H H8B -0.178(3) -0.150(3) 0.786(2) 0.035(6) Uiso d . 1 . .
H H9B -0.286(3) 0.146(3) 0.883(3) 0.041(6) Uiso d . 1 . .
H H4 0.386(3) 0.587(2) 0.610(2) 0.033(6) Uiso d . 1 . .
H H9A -0.401(3) 0.024(3) 0.793(2) 0.036(6) Uiso d . 1 . .
H H10A -0.331(3) 0.311(3) 0.731(2) 0.039(6) Uiso d . 1 . .
H H2 0.299(3) 0.541(3) 0.972(3) 0.042(7) Uiso d . 1 . .
H H11A -0.135(3) -0.023(3) 0.548(2) 0.040(6) Uiso d . 1 . .
H H12A -0.241(3) 0.215(3) 0.532(3) 0.049(7) Uiso d . 1 . .
H H8A -0.102(3) -0.044(2) 0.887(3) 0.033(6) Uiso d . 1 . .
H H11B -0.300(3) -0.076(3) 0.597(2) 0.037(6) Uiso d . 1 . .
H H7B 0.087(4) -0.208(3) 0.791(3) 0.058(8) Uiso d . 1 . .
H H12B -0.355(4) 0.101(3) 0.435(3) 0.055(8) Uiso d . 1 . .
H H7A 0.069(3) -0.121(3) 0.678(3) 0.052(7) Uiso d . 1 . .
H H10B -0.504(4) 0.259(3) 0.757(3) 0.052(7) Uiso d . 1 . .
H H4' -0.106(3) 0.125(3) 0.743(2) 0.037(6) Uiso d . 1 . .
Cl Cl 0.22010(6) 0.00390(7) 0.83918(7) 0.0572(2) Uani d . 1 . .
N N4 -0.18045(17) 0.05189(15) 0.73274(15) 0.0277(3) Uani d . 1 . .
C C8 -0.1068(2) -0.0703(2) 0.8042(2) 0.0333(4) Uani d . 1 . .
C C9 -0.3282(2) 0.1067(2) 0.7962(2) 0.0343(4) Uani d . 1 . .
O O8 -0.4535(2) 0.1794(2) 0.58892(18) 0.0535(4) Uani d . 1 . .
C C11 -0.2318(2) 0.0085(2) 0.5915(2) 0.0365(4) Uani d . 1 . .
C C10 -0.4054(3) 0.2269(2) 0.7217(3) 0.0469(5) Uani d . 1 . .
C C7 0.0592(2) -0.1150(2) 0.7678(2) 0.0405(4) Uani d . 1 . .
C C12 -0.3138(3) 0.1338(3) 0.5261(2) 0.0465(5) Uani d . 1 . .
C C5 0.2198(2) 0.43814(18) 0.62764(19) 0.0308(3) Uani d . 1 . .
N N2 0.47503(19) 0.70058(17) 0.84556(19) 0.0374(4) Uani d . 1 . .
C C2 0.2800(2) 0.51646(19) 0.8933(2) 0.0325(4) Uani d . 1 . .
O O1 0.0317(2) 0.25764(19) 0.67334(16) 0.0543(5) Uani d . 1 . .
C C4 0.3325(2) 0.54510(18) 0.6696(2) 0.0318(4) Uani d . 1 . .
C C3 0.3613(2) 0.58362(18) 0.80201(19) 0.0310(4) Uani d . 1 . .
C C1 0.1667(2) 0.40844(18) 0.85050(19) 0.0311(4) Uani d . 1 . .
C C6 0.1275(2) 0.35914(19) 0.71437(19) 0.0330(4) Uani d . 1 . .
N N3 0.0845(2) 0.34768(17) 0.95407(18) 0.0384(4) Uani d . 1 . .
N N1 0.1924(2) 0.40692(18) 0.48624(17) 0.0389(4) Uani d . 1 . .
O O5 0.5335(2) 0.76658(17) 0.76105(19) 0.0541(4) Uani d . 1 . .
O O2 -0.0347(2) 0.2682(2) 0.92512(19) 0.0603(5) Uani d . 1 . .
O O4 0.5057(2) 0.73018(19) 0.96342(19) 0.0542(4) Uani d . 1 . .
O O3 0.1342(2) 0.3801(2) 1.06775(18) 0.0568(5) Uani d . 1 . .
O O7 0.0693(3) 0.3444(3) 0.4397(2) 0.0808(7) Uani d . 1 . .
O O6 0.2896(3) 0.4530(3) 0.4174(2) 0.0902(8) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.011 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.148 0.159 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 N4 C11 . . 112.20(15) ?
C8 N4 C9 . . 110.07(14) ?
C11 N4 C9 . . 108.38(14) ?
C8 N4 H4' . . 106.9(15) ?
C11 N4 H4' . . 113.0(15) ?
C9 N4 H4' . . 106.1(15) ?
N4 C8 C7 . . 115.12(16) ?
N4 C8 H8B . . 107.4(14) ?
C7 C8 H8B . . 108.0(14) ?
N4 C8 H8A . . 106.8(16) ?
C7 C8 H8A . . 110.2(15) ?
H8B C8 H8A . . 109(2) ?
N4 C9 C10 . . 110.06(17) ?
N4 C9 H9B . . 105.2(15) ?
C10 C9 H9B . . 108.9(15) ?
N4 C9 H9A . . 105.1(14) ?
C10 C9 H9A . . 111.6(14) ?
H9B C9 H9A . . 116(2) ?
C12 O8 C10 . . 109.70(17) ?
N4 C11 C12 . . 109.86(17) ?
N4 C11 H11A . . 109.0(14) ?
C12 C11 H11A . . 111.4(14) ?
N4 C11 H11B . . 102.7(14) ?
C12 C11 H11B . . 116.2(14) ?
H11A C11 H11B . . 107(2) ?
O8 C10 C9 . . 111.16(18) ?
O8 C10 H10A . . 113.2(15) ?
C9 C10 H10A . . 109.7(14) ?
O8 C10 H10B . . 105.5(17) ?
C9 C10 H10B . . 111.4(17) ?
H10A C10 H10B . . 106(2) ?
C8 C7 Cl . . 113.24(15) ?
C8 C7 H7B . . 113.2(19) ?
Cl C7 H7B . . 107.2(18) ?
C8 C7 H7A . . 114.0(18) ?
Cl C7 H7A . . 105.7(17) ?
H7B C7 H7A . . 103(3) ?
O8 C12 C11 . . 111.16(18) ?
O8 C12 H12A . . 106.5(17) ?
C11 C12 H12A . . 110.6(16) ?
O8 C12 H12B . . 106.1(17) ?
C11 C12 H12B . . 108.8(16) ?
H12A C12 H12B . . 113(2) ?
C4 C5 C6 . . 124.17(18) ?
C4 C5 N1 . . 116.02(16) ?
C6 C5 N1 . . 119.80(15) ?
O4 N2 O5 . . 123.60(17) ?
O4 N2 C3 . . 118.95(17) ?
O5 N2 C3 . . 117.44(18) ?
C3 C2 C1 . . 118.96(18) ?
C3 C2 H2 . . 120.0(18) ?
C1 C2 H2 . . 121.0(18) ?
C5 C4 C3 . . 119.30(16) ?
C5 C4 H4 . . 118.7(15) ?
C3 C4 H4 . . 122.0(15) ?
C2 C3 C4 . . 121.53(16) ?
C2 C3 N2 . . 119.26(17) ?
C4 C3 N2 . . 119.18(16) ?
C2 C1 C6 . . 124.15(16) ?
C2 C1 N3 . . 114.57(17) ?
C6 C1 N3 . . 121.27(15) ?
O1 C6 C1 . . 125.59(17) ?
O1 C6 C5 . . 122.46(18) ?
C1 C6 C5 . . 111.90(15) ?
O3 N3 O2 . . 121.69(18) ?
O3 N3 C1 . . 118.95(17) ?
O2 N3 C1 . . 119.35(18) ?
O7 N1 O6 . . 121.2(2) ?
O7 N1 C5 . . 119.83(18) ?
O6 N1 C5 . . 118.78(18) ?
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
Cl C7 . 1.788(2) ?
N4 C8 . 1.497(2) ?
N4 C11 . 1.503(2) ?
N4 C9 . 1.504(2) ?
N4 H4' . 0.91(2) ?
C8 C7 . 1.500(3) ?
C8 H8B . 0.94(2) ?
C8 H8A . 0.87(3) ?
C9 C10 . 1.510(3) ?
C9 H9B . 0.98(3) ?
C9 H9A . 0.97(2) ?
O8 C12 . 1.420(3) ?
O8 C10 . 1.426(3) ?
C11 C12 . 1.517(3) ?
C11 H11A . 0.98(3) ?
C11 H11B . 0.97(2) ?
C10 H10A . 0.98(3) ?
C10 H10B . 0.96(3) ?
C7 H7B . 0.93(3) ?
C7 H7A . 0.94(3) ?
C12 H12A . 0.96(3) ?
C12 H12B . 0.99(3) ?
C5 C4 . 1.374(2) ?
C5 C6 . 1.455(2) ?
C5 N1 . 1.460(3) ?
N2 O4 . 1.228(3) ?
N2 O5 . 1.229(2) ?
N2 C3 . 1.449(2) ?
C2 C3 . 1.382(3) ?
C2 C1 . 1.386(2) ?
C2 H2 . 0.83(3) ?
O1 C6 . 1.250(2) ?
C4 C3 . 1.383(3) ?
C4 H4 . 0.89(2) ?
C1 C6 . 1.450(3) ?
C1 N3 . 1.456(2) ?
N3 O3 . 1.220(2) ?
N3 O2 . 1.225(2) ?
N1 O7 . 1.206(3) ?
N1 O6 . 1.210(3) ?
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
N4 H4' O1 . 0.91(3) 1.89(3) 2.718(2) 151.2(19)
N4 H4' O2 . 0.91(3) 2.25(2) 2.896(2) 127.6(17)
C2 H2 O3 . 0.83(3) 2.34(3) 2.637(3) 102(2)
C2 H2 O4 . 0.83(2) 2.45(2) 2.723(3) 101(2)
C4 H4 O6 . 0.90(3) 2.34(3) 2.667(3) 101.7(15)
C7 H7A O7 2_556 0.93(3) 2.54(3) 3.026(3) 113(2)
C8 H8B O5 1_445 0.94(3) 2.47(2) 3.290(2) 146(2)
C9 H9A O5 1_445 0.97(3) 2.45(3) 3.341(2) 154(2)
C9 H9B O2 . 0.97(3) 2.34(3) 2.985(3) 123(2)
C12 H12A O1 . 0.96(3) 2.57(2) 3.254(3) 129(2)
