#------------------------------------------------------------------------------
#$Date: 2016-02-14 15:26:36 +0100 (dom 14 de feb de 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/01/2010130.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_2010130
loop_
_publ_author_name
'Frydenvang, Karla'
'Trickey, Peter'
'Jensen, Birthe'
_publ_section_title
;
 Ethoxycarbonylcholine picrate hemihydrate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1839
_journal_page_last               1841
_journal_paper_doi               10.1107/S0108270194002921
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C8 H18 N O3 +1,C6 H2 N3 O7 -1,0.5(H2 O)'
_chemical_formula_sum            'C14 H21 N4 O10.5'
_chemical_formula_weight         413.35
_chemical_melting_point          .388E-305
_chemical_name_common            'Ethoxycarbonylcholine Picrate Hemihydrate'
_chemical_name_systematic        ' Ethoxycarbonylcholine Picrate Hemihydrate'
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 102.86(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.623(3)
_cell_length_b                   7.432(2)
_cell_length_c                   21.197(5)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      22.05
_cell_measurement_theta_min      16.64
_cell_volume                     1785.1(8)
_computing_data_reduction        'Blessing (1987)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      105(2)
_diffrn_measurement_device       'CAD4 Enraf Nonius'
_diffrn_measurement_method       'profile data from ω/2θ scan'
_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  0.010
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            15033
_diffrn_reflns_theta_max         38.96
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_count 600
_diffrn_standards_interval_time  166
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       needles
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.116
_refine_ls_goodness_of_fit_obs   1.096
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         10340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_restrained_S_obs      1.096
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_obs          0.0458
_refine_ls_shift/esd_max         0.125
_refine_ls_shift/esd_mean        0.016
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
; calc w = 1/[\s^2^(Fo^2^) + (0.0486P)^2^ + 0.5810P]
  where P = (Fo^2^ + 2Fc^2^)/3
;
_refine_ls_wR_factor_all         0.1287
_refine_ls_wR_factor_obs         0.1073
_reflns_number_observed          8028
_reflns_number_total             10364
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ab1157.cif
_cod_data_source_block           etcopi
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_original_formula_sum        'C14 H21 N4 O10.50'
_cod_database_code               2010130
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y, -z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
C12 0.72773(9) 0.14570(10) 0.58765(4) 0.0192(2) Uani d . 1 . C
C11 0.64002(8) 0.11540(10) 0.52487(4) 0.0182(2) Uani d . 1 . C
O1 0.66793(6) 0.23929(9) 0.47713(3) 0.01570(10) Uani d . 1 . O
C2 0.60276(7) 0.21420(10) 0.41765(4) 0.01350(10) Uani d . 1 . C
O3 0.53192(6) 0.09590(10) 0.40046(3) 0.01910(10) Uani d . 1 . O
O4 0.63013(6) 0.34367(9) 0.37971(3) 0.01530(10) Uani d . 1 . O
C5 0.56825(8) 0.33050(10) 0.31244(4) 0.01450(10) Uani d . 1 . C
C6 0.59953(7) 0.49470(10) 0.27776(4) 0.01330(10) Uani d . 1 . C
N7 0.52781(6) 0.66150(10) 0.28283(3) 0.01300(10) Uani d . 1 . N
C9 0.40504(8) 0.64010(10) 0.24266(5) 0.0190(2) Uani d . 1 . C
C10 0.58457(9) 0.81790(10) 0.25668(5) 0.0197(2) Uani d . 1 . C
C8 0.52281(9) 0.70170(10) 0.35149(4) 0.0196(2) Uani d . 1 . C
C21 0.08136(7) 0.23100(10) 0.37701(4) 0.01290(10) Uani d . 1 . C
C22 0.18049(7) 0.30970(10) 0.42361(4) 0.01330(10) Uani d . 1 . C
C23 0.18016(7) 0.34450(10) 0.48747(4) 0.01380(10) Uani d . 1 . C
C24 0.08024(7) 0.30420(10) 0.51062(4) 0.01340(10) Uani d . 1 . C
C25 -0.01992(7) 0.22950(10) 0.47045(4) 0.01290(10) Uani d . 1 . C
C26 -0.01887(7) 0.19830(10) 0.40689(4) 0.01210(10) Uani d . 1 . C
O21 0.08129(6) 0.18820(10) 0.32038(3) 0.01880(10) Uani d . 1 . O
N22 0.28822(6) 0.35800(10) 0.40341(4) 0.01590(10) Uani d . 1 . N
O221 0.28382(7) 0.38120(10) 0.34528(4) 0.0243(2) Uani d . 1 . O
O222 0.37919(6) 0.37850(10) 0.44544(4) 0.0243(2) Uani d . 1 . O
N24 0.07930(7) 0.34120(10) 0.57698(3) 0.01590(10) Uani d . 1 . N
O241 0.16975(7) 0.39950(10) 0.61295(3) 0.02280(10) Uani d . 1 . O
O242 -0.01223(7) 0.31360(10) 0.59560(3) 0.0255(2) Uani d . 1 . O
N26 -0.12732(6) 0.12500(10) 0.36712(3) 0.01380(10) Uani d . 1 . N
O261 -0.18295(6) 0.01410(10) 0.39189(4) 0.02100(10) Uani d . 1 . O
O262 -0.16004(6) 0.17830(10) 0.31133(3) 0.0234(2) Uani d . 1 . O
O8 0.2500 0.0356(2) 0.2500 0.0272(2) Uani d S 1 . O
H8 0.283(2) 0.101(3) 0.2310(10) 0.050 Uiso d . 1 . H
H121 0.723(2) 0.271(3) 0.6020(10) 0.050 Uiso d . 1 . H
H122 0.811(2) 0.119(3) 0.5830(10) 0.050 Uiso d . 1 . H
H123 0.709(2) 0.060(3) 0.6200(10) 0.050 Uiso d . 1 . H
H111 0.558(2) 0.139(3) 0.5280(10) 0.050 Uiso d . 1 . H
H112 0.645(2) -0.010(3) 0.5090(10) 0.050 Uiso d . 1 . H
H51 0.600(2) 0.226(3) 0.2940(10) 0.050 Uiso d . 1 . H
H52 0.483(2) 0.317(3) 0.3100(10) 0.050 Uiso d . 1 . H
H61 0.586(2) 0.468(3) 0.2320(10) 0.050 Uiso d . 1 . H
H62 0.681(2) 0.531(3) 0.2952(9) 0.050 Uiso d . 1 . H
H91 0.361(2) 0.751(3) 0.2480(10) 0.050 Uiso d . 1 . H
H92 0.370(2) 0.535(3) 0.2580(10) 0.050 Uiso d . 1 . H
H93 0.412(2) 0.624(3) 0.1980(10) 0.050 Uiso d . 1 . H
H101 0.594(2) 0.782(3) 0.2140(10) 0.050 Uiso d . 1 . H
H102 0.531(2) 0.923(3) 0.2533(9) 0.050 Uiso d . 1 . H
H103 0.659(2) 0.842(3) 0.2860(10) 0.050 Uiso d . 1 . H
H81 0.603(2) 0.710(3) 0.3780(10) 0.050 Uiso d . 1 . H
H82 0.481(2) 0.604(3) 0.3660(10) 0.050 Uiso d . 1 . H
H83 0.482(2) 0.816(3) 0.3510(10) 0.050 Uiso d . 1 . H
H25 -0.088(2) 0.204(3) 0.4860(10) 0.050 Uiso d . 1 . H
H23 0.247(2) 0.402(3) 0.5150(10) 0.050 Uiso d . 1 . H
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_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C11 C12 . . 107.95(7) yes
C2 O1 C11 . . 113.67(7) yes
O3 C2 O1 . . 126.52(8) yes
O3 C2 O4 . . 125.57(8) yes
O1 C2 O4 . . 107.92(7) yes
C2 O4 C5 . . 114.23(7) yes
O4 C5 C6 . . 107.67(7) yes
C5 C6 N7 . . 115.59(7) yes
C9 N7 C8 . . 109.58(7) yes
C9 N7 C10 . . 108.28(7) yes
C8 N7 C10 . . 108.62(7) yes
C9 N7 C6 . . 110.04(7) yes
C8 N7 C6 . . 111.94(7) yes
C10 N7 C6 . . 108.30(7) yes
C22 C21 C26 . . 110.92(7) yes
C23 C22 C21 . . 124.34(7) yes
C22 C23 C24 . . 119.42(8) yes
C23 C24 C25 . . 121.28(7) yes
C26 C25 C24 . . 118.61(7) yes
C25 C26 C21 . . 125.39(7) yes
O21 C21 C22 . . 125.90(8) yes
O21 C21 C26 . . 123.10(8) yes
N22 C22 C21 . . 119.99(7) yes
C23 C22 N22 . . 115.66(7) yes
O222 N22 O221 . . 122.92(8) yes
O222 N22 C22 . . 118.30(8) yes
O221 N22 C22 . . 118.76(8) yes
C23 C24 N24 . . 119.58(7) yes
C25 C24 N24 . . 119.14(7) yes
O242 N24 O241 . . 122.64(8) yes
O242 N24 C24 . . 118.52(7) yes
O241 N24 C24 . . 118.84(8) yes
N26 C26 C21 . . 118.73(7) yes
C25 C26 N26 . . 115.88(7) yes
O262 N26 O261 . . 123.17(8) yes
O262 N26 C26 . . 118.73(7) yes
O261 N26 C26 . . 118.10(7) yes
C11 C12 H121 . . 110.0(10) ?
C11 C12 H122 . . 111.0(10) ?
H121 C12 H122 . . 109(2) ?
C11 C12 H123 . . 108.0(10) ?
H121 C12 H123 . . 111(2) ?
H122 C12 H123 . . 108(2) ?
O1 C11 H111 . . 108.0(10) ?
C12 C11 H111 . . 113.0(10) ?
O1 C11 H112 . . 109.0(10) ?
C12 C11 H112 . . 111.0(10) ?
H111 C11 H112 . . 109(2) ?
O4 C5 H51 . . 108.0(10) ?
C6 C5 H51 . . 107.0(10) ?
O4 C5 H52 . . 109.0(10) ?
C6 C5 H52 . . 114.0(10) ?
H51 C5 H52 . . 111(2) ?
C5 C6 H61 . . 108.0(10) ?
N7 C6 H61 . . 106.0(10) ?
C5 C6 H62 . . 111.0(10) ?
N7 C6 H62 . . 104.0(10) ?
H61 C6 H62 . . 111(2) ?
N7 C8 H81 . . 109.0(10) ?
N7 C8 H82 . . 107.0(10) ?
H81 C8 H82 . . 110(2) ?
N7 C8 H83 . . 107.0(10) ?
H81 C8 H83 . . 111(2) ?
H82 C8 H83 . . 112(2) ?
N7 C9 H91 . . 107.0(10) ?
N7 C9 H92 . . 109.0(10) ?
H91 C9 H92 . . 112(2) ?
N7 C9 H93 . . 107.0(10) ?
H91 C9 H93 . . 111(2) ?
H92 C9 H93 . . 111(2) ?
N7 C10 H101 . . 106.0(10) ?
N7 C10 H102 . . 109.0(10) ?
H101 C10 H102 . . 110(2) ?
N7 C10 H103 . . 108.0(10) ?
H101 C10 H103 . . 113(2) ?
H102 C10 H103 . . 111(2) ?
C22 C23 H23 . . 120.0(10) ?
C24 C23 H23 . . 120.0(10) ?
C26 C25 H25 . . 120.0(10) ?
C24 C25 H25 . . 121.0(10) ?
O21 H8 O8 4_656 4_656 157(2) no
C8 H83 O3 . 1_565 134(2) ?
C9 H91 O8 . 1_565 175(2) ?
C6 H62 O241 . 3_666 148(2) ?
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
C12 C11 . 1.5020(10) yes
C11 O1 . 1.4570(10) yes
O1 C2 . 1.3320(10) yes
C2 O3 . 1.2040(10) yes
C2 O4 . 1.3370(10) yes
O4 C5 . 1.4500(10) yes
C5 C6 . 1.5100(10) yes
C6 N7 . 1.5110(10) yes
N7 C8 . 1.4990(10) yes
N7 C9 . 1.4990(10) yes
N7 C10 . 1.5020(10) yes
C21 C22 . 1.4630(10) yes
C22 C23 . 1.3790(10) yes
C23 C24 . 1.3900(10) yes
C24 C25 . 1.3960(10) yes
C25 C26 . 1.3700(10) yes
C21 C26 . 1.4650(10) yes
C21 O21 . 1.2420(10) yes
C22 N22 . 1.4560(10) yes
N22 O222 . 1.2310(10) yes
N22 O221 . 1.2340(10) yes
C24 N24 . 1.4360(10) yes
N24 O242 . 1.2320(10) yes
N24 O241 . 1.2320(10) yes
C26 N26 . 1.4570(10) yes
N26 O262 . 1.2250(10) yes
N26 O261 . 1.2350(10) yes
O8 H8 . 0.78(2) no
C12 H121 . 0.99(2) ?
C12 H122 . 1.02(2) ?
C12 H123 . 1.00(2) ?
C11 H111 . 0.99(2) ?
C11 H112 . 1.00(2) ?
C5 H51 . 0.98(2) ?
C5 H52 . 0.99(2) ?
C6 H61 . 0.96(2) ?
C6 H62 . 0.97(2) ?
C8 H81 . 0.98(2) ?
C8 H82 . 0.97(2) ?
C8 H83 . 0.98(2) ?
C9 H91 . 0.99(2) ?
C9 H92 . 0.97(2) ?
C9 H93 . 0.97(2) ?
C10 H101 . 0.98(2) ?
C10 H102 . 0.99(2) ?
C10 H103 . 0.97(2) ?
C23 H23 . 0.96(2) ?
C25 H25 . 0.94(2) ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O21 O8 2.9420(10) 4_656 no
O21 H8 2.21(2) 4_656 no
C8 O3 3.1020(10) 1_565 ?
H83 O3 2.34(2) 1_565 ?
C9 O8 3.470(2) 1_565 ?
H91 O8 2.49(2) 1_565 ?
C6 O241 3.2270(10) 3_666 ?
H62 O241 2.36(2) 3_666 ?
C12 O242 3.2400(10) 1_655 ?
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
_geom_torsion_publ_flag
C12 C11 O1 C2 174.21(8) yes
C11 O1 C2 O4 175.33(7) yes
O1 C2 O4 C5 178.17(7) yes
C2 O4 C5 C6 174.59(7) yes
O4 C5 C6 N7 -83.60(9) yes
C5 C6 N7 C8 49.93(9) yes
C5 C6 N7 C9 -72.17(9) yes
C5 C6 N7 C10 169.65(7) yes
O3 C2 O1 C11 -5.00(10) ?
O3 C2 O4 C5 -1.50(10) ?
C25 C26 C21 C22 -2.50(10) ?
C26 C21 C22 C23 1.40(10) ?
C21 C22 C23 C24 -0.20(10) ?
C22 C23 C24 C25 -0.10(10) ?
C23 C24 C25 C26 -0.90(10) ?
C24 C25 C26 C21 2.30(10) ?
C21 C22 N22 O221 20.70(10) ?
C21 C22 N22 O222 -161.18(8) ?
C23 C22 N22 O221 -158.91(9) ?
C23 C22 N22 O222 19.30(10) ?
C23 C24 N24 O241 -3.80(10) ?
C23 C24 N24 O242 176.12(9) ?
C25 C24 N24 O241 176.74(9) ?
C25 C24 N24 O242 -3.40(10) ?
C25 C26 N26 O261 -37.40(10) ?
C25 C26 N26 O262 141.38(9) ?
C21 C26 N26 O261 142.09(8) ?
C21 C26 N26 O262 -39.20(10) ?
