#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/46/2004609.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_2004609
loop_
_publ_author_name
'Baggio, R.'
'Baggio, S.'
'Pardo, M. I.'
'Capparelli, M. V.'
_publ_section_title
;
 Narceine Hydrochloride Trihydrate
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              703
_journal_page_last               705
_journal_paper_doi               10.1107/S0108270195012479
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C23 H27 N1 O8,H1 Cl1,3H2 O1'
_chemical_formula_sum            'C23 H34 Cl N O11'
_chemical_formula_weight         535.96
_chemical_name_common            'narceine hydrochloride'
_chemical_name_systematic
;
N,N-Dimethyl-2-[5-(2-carboxy-3,4-dimethoxybenzoylmethyl)-4-methoxy-1,3-
benzodioxol-6-yl]ethylammonium Chloride (Narceine) Trihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                100.89(3)
_cell_angle_beta                 114.89(3)
_cell_angle_gamma                77.51(3)
_cell_formula_units_Z            2
_cell_length_a                   11.805(4)
_cell_length_b                   12.428(3)
_cell_length_c                   10.021(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.0
_cell_measurement_theta_min      17.3
_cell_volume                     1294.1(8)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software (Molecule Structure Corporation,
 1993)
;
_computing_data_reduction        'MSC/AFC Diffractometer Control Software'
_computing_molecular_graphics    'XP  SHELXTL/PC'
_computing_publication_material  'CIFTAB SHELXL93, PARST (Nardelli,1983)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'XS SHELXTL/PC (Sheldrick,1991)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Rigaku AFC7S'
_diffrn_measurement_method       ω-2θ
_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  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4846
_diffrn_reflns_theta_max         25.28
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.420
_refine_ls_extinction_coef       0.006(2)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.026
_refine_ls_goodness_of_fit_obs   1.103
_refine_ls_hydrogen_treatment
;
Hydrogen atoms from water molecules refined with constrained
distance to oxygen. Hydrogen atoms defined by the structure,
placed at calculated positions and allowed to ride on the host
atom.
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4571
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.028
_refine_ls_restrained_S_obs      1.104
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_obs          0.0485
_refine_ls_shift/esd_max         0.022
_refine_ls_shift/esd_mean        0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0757P)²+0.7150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1627
_refine_ls_wR_factor_obs         0.1366
_reflns_number_observed          2899
_reflns_number_total             4572
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ha1145.cif
_cod_data_source_block           narce
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (34
times).

'_geom_angle_publ_flag' value 'N' changed to 'n' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (48
times).

'_geom_torsion_publ_flag' value 'N' changed to 'n' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (66 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0757P)^2^+0.7150P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0757P)^2^+0.7150P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1294.0(7)
_cod_database_code               2004609
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_occupancy
_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_type_symbol
Cl 1 .12247(8) .33927(8) .36092(10) .0760(3) Uani d . Cl
O1 1 .3174(2) .1498(2) -0.1724(2) .0490(5) Uani d . O
O2 1 .1758(2) .0031(2) -0.1886(2) .0563(5) Uani d . O
O3 1 .4191(2) .3614(2) .0688(2) .0625(6) Uani d D O
H3 1 .3548(2) .3818(2) .1037(2) .080 Uiso d RD H
O4 1 .5718(2) .2205(2) .0967(3) .0757(7) Uani d . O
O5 1 .9111(2) .1658(2) .8530(3) .0662(6) Uani d . O
O6 1 .8645(2) .3143(2) 1.0087(2) .0710(7) Uani d . O
O7 1 .7119(2) .0813(2) .5716(3) .0688(6) Uani d . O
O8 1 .4999(3) .2965(2) .3667(2) .0736(7) Uani d . O
N 1 .2580(2) .5306(2) .5703(3) .0602(7) Uani d . N
H0A 1 .2062(2) .4799(2) .5205(3) .080 Uiso d R H
C1 1 .5409(3) .3118(2) .7360(3) .0468(7) Uani d . C
C2 1 .6379(3) .3488(2) .8631(3) .0528(7) Uani d . C
H2A 1 .6214(3) .4096(2) .9307(3) .080 Uiso d R H
C3 1 .7570(3) .2960(2) .8878(3) .0522(7) Uani d . C
C4 1 .7845(3) .2087(2) .7937(3) .0492(7) Uani d . C
C5 1 .6917(3) .1706(2) .6675(3) .0490(7) Uani d . C
C6 1 .5672(3) .2229(2) .6388(3) .0456(7) Uani d . C
C7 1 .4656(3) .1786(3) .5019(3) .0517(7) Uani d . C
H7A 1 .3868(3) .1992(3) .5134(3) .080 Uiso d R H
H7B 1 .4840(3) .0991(3) .4921(3) .080 Uiso d R H
C8 1 .4504(3) .2186(2) .3614(3) .0467(7) Uani d . C
C9 1 .3749(3) .1622(2) .2190(3) .0423(6) Uani d . C
C10 1 .3802(2) .1835(2) .0886(3) .0410(6) Uani d . C
C11 1 .3118(3) .1289(2) -.0444(3) .0418(6) Uani d . C
C12 1 .2370(3) .0523(2) -.0526(3) .0437(6) Uani d . C
C13 1 .2310(3) .0325(2) .0759(3) .0483(7) Uani d . C
H13A 1 .1794(3) -.0191(2) .0718(3) .080 Uiso d R H
C14 1 .2992(3) .0870(2) .2084(3) .0467(7) Uani d . C
H14A 1 .2946(3) .0729(2) .2968(3) .080 Uiso d R H
C15 1 .9631(3) .2493(3) .9693(4) .0735(10) Uani d . C
H15A 1 1.0002(3) .2954(3) .9370(4) .080 Uiso d R H
H15B 1 1.0279(3) .2157(3) 1.0534(4) .080 Uiso d R H
C16 1 .4111(3) .3758(3) .7072(3) .0547(7) Uani d . C
H16A 1 .4033(3) .4047(3) .7993(3) .080 Uiso d R H
H16B 1 .3488(3) .3279(3) .6528(3) .080 Uiso d R H
C17 1 .3897(3) .4702(2) .6190(3) .0531(7) Uani d . C
H17A 1 .4472(3) .5213(2) .6785(3) .080 Uiso d R H
H17B 1 .4083(3) .4410(2) .5334(3) .080 Uiso d R H
C18 1 .2224(4) .5869(4) .6939(5) .0947(14) Uani d . C
H18A 1 .1358(4) .6219(4) .6552(5) .080 Uiso d R H
H18B 1 .2324(4) .5333(4) .7571(5) .080 Uiso d R H
H18C 1 .2756(4) .6420(4) .7497(5) .080 Uiso d R H
C19 1 .2377(4) .6086(3) .4640(5) .0951(15) Uani d . C
H19A 1 .1511(4) .6436(3) .4276(5) .080 Uiso d R H
H19B 1 .2917(4) .6641(3) .5131(5) .080 Uiso d R H
H19C 1 .2574(4) .5686(3) .3827(5) .080 Uiso d R H
C20 1 .8158(4) .0728(4) .5343(5) .0942(13) Uani d . C
H20A 1 .8284(4) .0010(4) .4823(5) .080 Uiso d R H
H20B 1 .8000(4) .1291(4) .4721(5) .080 Uiso d R H
H20C 1 .8902(4) .0826(4) .6228(5) .080 Uiso d R H
C21 1 .4668(3) .2569(3) .0878(3) .0500(7) Uani d . C
C22 1 .4071(3) .0682(3) -0.2158(4) .0629(9) Uani d . C
H22A 1 .3987(3) .0795(3) -0.3120(4) .080 Uiso d R H
H22B 1 .4915(3) .0758(3) -0.1453(4) .080 Uiso d R H
H22C 1 .3908(3) -.0049(3) -0.2190(4) .080 Uiso d R H
C23 1 .1136(4) -.0868(3) -0.1989(4) .0710(10) Uani d . C
H23A 1 .0779(4) -0.1179(3) -0.3004(4) .080 Uiso d R H
H23B 1 .1736(4) -0.1427(3) -0.1401(4) .080 Uiso d R H
H23C 1 .0475(4) -.0602(3) -0.1634(4) .080 Uiso d R H
O1w 1 .2084(3) .4252(3) .1085(4) .1121(11) Uani d D O
H1wa 1 .1511(3) .4071(3) .1403(4) .050 Uiso d RD H
H1wb 1 .1596(3) .4294(3) .0025(4) .050 Uiso d RD H
O2w 1 .0808(3) .2641(3) -0.3758(4) .1364(15) Uani d D O
H2wa 1 .1579(3) .2301(3) -0.3086(4) .050 Uiso d RD H
H2wb 1 .0953(3) .2697(3) -0.4594(4) .050 Uiso d RD H
O3w 1 .0512(5) .4476(4) -0.1732(5) .166(2) Uani d D O
H3wa 1 -.0192(5) .5049(4) -0.1889(5) .050 Uiso d RD H
H3wb 1 .0706(5) .4463(4) -0.2585(5) .050 Uiso d RD 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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C11 O1 C22 112.5(2) n
C12 O2 C23 117.1(2) n
C4 O5 C15 102.8(2) n
C3 O6 C15 104.0(2) n
C5 O7 C20 118.0(3) n
C18 N C19 111.7(3) n
C18 N C17 113.7(3) n
C19 N C17 109.9(3) n
C2 C1 C6 120.4(3) n
C2 C1 C16 116.1(3) n
C6 C1 C16 123.4(3) n
C3 C2 C1 117.3(3) n
C2 C3 O6 127.1(3) n
C2 C3 C4 123.0(3) n
O6 C3 C4 109.8(3) n
C5 C4 C3 121.2(3) n
C5 C4 O5 128.5(3) n
C3 C4 O5 110.2(3) n
C4 C5 O7 124.2(3) n
C4 C5 C6 117.3(3) n
O7 C5 C6 118.4(3) n
C1 C6 C5 120.8(3) n
C1 C6 C7 122.3(3) n
C5 C6 C7 116.9(3) n
C6 C7 C8 114.4(2) n
O8 C8 C9 120.8(2) n
O8 C8 C7 120.4(3) n
C9 C8 C7 118.8(2) n
C14 C9 C10 118.7(2) n
C14 C9 C8 122.0(2) n
C10 C9 C8 119.3(2) n
C11 C10 C9 119.3(2) n
C11 C10 C21 117.1(2) n
C9 C10 C21 123.4(2) n
C10 C11 O1 119.2(2) n
C10 C11 C12 121.1(2) n
O1 C11 C12 119.8(2) n
O2 C12 C13 125.0(3) n
O2 C12 C11 115.5(2) n
C13 C12 C11 119.4(2) n
C14 C13 C12 119.5(3) n
C13 C14 C9 122.0(3) n
O6 C15 O5 108.5(3) n
C1 C16 C17 109.0(2) n
N C17 C16 112.8(3) n
O4 C21 O3 121.3(3) n
O4 C21 C10 121.6(3) n
O3 C21 C10 117.0(3) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 1.387(3) y
O1 C22 1.448(4) y
O2 C12 1.342(3) y
O2 C23 1.429(4) y
O3 C21 1.315(4) y
O4 C21 1.195(4) y
O5 C4 1.378(4) y
O5 C15 1.425(4) y
O6 C3 1.362(3) y
O6 C15 1.423(4) y
O7 C5 1.374(4) y
O7 C20 1.404(5) y
O8 C8 1.217(3) y
N C18 1.478(5) y
N C19 1.485(5) y
N C17 1.488(4) y
C1 C2 1.387(4) y
C1 C6 1.402(4) y
C1 C16 1.500(4) y
C2 C3 1.357(4) y
C3 C4 1.375(4) y
C4 C5 1.362(4) y
C5 C6 1.402(4) y
C6 C7 1.496(4) y
C7 C8 1.509(4) y
C8 C9 1.463(4) y
C9 C14 1.389(4) y
C9 C10 1.410(4) y
C10 C11 1.370(4) y
C10 C21 1.513(4) y
C11 C12 1.402(4) y
C12 C13 1.388(4) y
C13 C14 1.366(4) y
C16 C17 1.516(4) y
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
O3 O1w 2.613(5) 1_555 yes
C20 O5 2.990(5) 1_555 yes
O1w O3w 2.675(6) 1_555 yes
O2w O1 2.925(4) 1_555 yes
O3w Cl 3.323(5) 2_565 yes
O3w O2w 2.819(7) 1_555 yes
N Cl 3.090(3) 1_555 yes
O1w Cl 3.495(5) 1_555 yes
C19 O8 3.204(5) 2_666 yes
O2w Cl 3.209(5) 1_554 yes
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
C6 C1 C2 C3 0.1(4) n
C16 C1 C2 C3 -176.7(3) n
C1 C2 C3 O6 -175.9(3) n
C1 C2 C3 C4 -0.1(5) n
C15 O6 C3 C2 -171.9(3) n
C15 O6 C3 C4 11.9(3) n
C2 C3 C4 C5 0.5(5) n
O6 C3 C4 C5 176.9(3) n
C2 C3 C4 O5 -175.0(3) n
O6 C3 C4 O5 1.5(4) n
C15 O5 C4 C5 170.9(3) n
C15 O5 C4 C3 -14.0(3) n
C3 C4 C5 O7 -177.5(3) n
O5 C4 C5 O7 -2.9(5) n
C3 C4 C5 C6 -0.8(4) n
O5 C4 C5 C6 173.8(3) n
C20 O7 C5 C4 -44.0(4) n
C20 O7 C5 C6 139.3(3) n
C2 C1 C6 C5 -0.5(4) n
C16 C1 C6 C5 176.1(3) n
C2 C1 C6 C7 178.8(3) n
C16 C1 C6 C7 -4.6(4) n
C4 C5 C6 C1 0.8(4) n
O7 C5 C6 C1 177.7(2) n
C4 C5 C6 C7 -178.5(2) n
O7 C5 C6 C7 -1.7(4) n
C1 C6 C7 C8 100.1(3) n
C5 C6 C7 C8 -80.6(3) n
C6 C7 C8 O8 -13.8(4) n
C6 C7 C8 C9 166.4(3) n
O8 C8 C9 C14 -168.2(3) n
C7 C8 C9 C14 11.6(4) n
O8 C8 C9 C10 12.7(4) n
C7 C8 C9 C10 -167.5(3) n
C14 C9 C10 C11 -0.6(4) n
C8 C9 C10 C11 178.5(2) n
C14 C9 C10 C21 -175.2(3) n
C8 C9 C10 C21 3.9(4) n
C9 C10 C11 O1 -179.9(2) n
C21 C10 C11 O1 -5.0(4) n
C9 C10 C11 C12 -0.1(4) n
C21 C10 C11 C12 174.8(3) n
C22 O1 C11 C10 97.1(3) n
C22 O1 C11 C12 -82.7(3) n
C23 O2 C12 C13 -8.8(4) n
C23 O2 C12 C11 171.2(3) n
C10 C11 C12 O2 -179.1(2) n
O1 C11 C12 O2 0.7(4) n
C10 C11 C12 C13 0.8(4) n
O1 C11 C12 C13 -179.4(2) n
O2 C12 C13 C14 179.1(3) n
C11 C12 C13 C14 -0.8(4) n
C12 C13 C14 C9 0.1(4) n
C10 C9 C14 C13 0.6(4) n
C8 C9 C14 C13 -178.5(3) n
C3 O6 C15 O5 -20.8(3) n
C4 O5 C15 O6 21.4(3) n
C2 C1 C16 C17 88.4(3) n
C6 C1 C16 C17 -88.3(3) n
C18 N C17 C16 63.5(4) n
C19 N C17 C16 -170.4(3) n
C1 C16 C17 N 173.4(3) n
C11 C10 C21 O4 -85.5(4) n
C9 C10 C21 O4 89.2(4) n
C11 C10 C21 O3 91.0(3) n
C9 C10 C21 O3 -94.3(3) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21138494
