#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/34/2013411.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_2013411
loop_
_publ_author_name
'M. Barboiu'
'A. van der Lee'
_publ_section_title
;
 Hydrogen bonding in
 calcium--trifluoromethanesulfonate--1,3-di-4-pyridylurea--methanol
 (1/2/2/4)
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m366
_journal_page_last               m368
_journal_paper_doi               10.1107/S0108270103011454
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac
'Ca 2+, 2C F3 O3 S 1-, 2C11 H10 N4 O, 4C H4 O'
_chemical_formula_moiety
'Ca 2+, 2C F3 O3 S 1-, 2C11 H10 N4 O, 4C H4 O'
_chemical_formula_sum            'C28 H36 Ca F6 N8 O12 S2'
_chemical_formula_weight         894.84
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                98.950(10)
_cell_angle_beta                 97.140(10)
_cell_angle_gamma                94.030(10)
_cell_formula_units_Z            1
_cell_length_a                   9.1570(10)
_cell_length_b                   9.7680(10)
_cell_length_c                   11.366(2)
_cell_measurement_reflns_used    4175
_cell_measurement_temperature    173
_cell_measurement_theta_max      23.20
_cell_measurement_theta_min      1.75
_cell_volume                     992.3(2)
_computing_cell_refinement       'Crysalis RED (Oxford Diffraction, 2002)'
_computing_data_collection       'Crysalis CCD (Oxford Diffraction, 2002)'
_computing_data_reduction        'Crysalis RED (2002)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  PLATON
_computing_structure_refinement
;
CRYSTALS (Watkin et al., 2001), SHELXL97 (Sheldrick, 1997) and
WinGX (Version 1.64.05; Farrugia, 1997)
;
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 17
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur CCD'
_diffrn_measurement_method       area-detector
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17908
_diffrn_reflns_reduction_process RED
_diffrn_reflns_theta_full        28.49
_diffrn_reflns_theta_max         28.49
_diffrn_reflns_theta_min         3.23
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  30
_exptl_absorpt_coefficient_mu    0.358
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   '(Schwarzenbach & Flack, 1991)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.313
_refine_ls_extinction_coef       0.0018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.695
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         6255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.695
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.023P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0602
_refine_ls_wR_factor_ref         0.0663
_reflns_number_gt                2931
_reflns_number_total             5013
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            de1212.cif
_cod_data_source_block           I
_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.

'_exptl_absorpt_correction_type' value 'Gaussian'
changed to 'gaussian' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2013411
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
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
Ca1 1.0000 0.0000 0.0000 0.02014(11) Uani d S 1 . . Ca
O2 1.13628(12) 0.20800(12) -0.01142(11) 0.0316(3) Uani d . 1 . . O
H2 1.1087 0.2472 -0.0679 0.047 Uiso calc R 1 . . H
C2 1.28346(19) 0.26111(19) 0.03850(17) 0.0423(5) Uani d . 1 . . C
H2B 1.3085 0.2300 0.1139 0.063 Uiso calc R 1 . . H
H2C 1.2907 0.3610 0.0511 0.063 Uiso calc R 1 . . H
H2D 1.3504 0.2282 -0.0159 0.063 Uiso calc R 1 . . H
O3 0.85768(12) 0.01471(11) -0.18068(10) 0.0302(3) Uani d . 1 . . O
H3 0.8003 0.0748 -0.1867 0.045 Uiso calc R 1 . . H
C3 0.8362(2) -0.08435(19) -0.28842(16) 0.0440(5) Uani d . 1 . . C
H3A 0.8893 -0.1634 -0.2762 0.066 Uiso calc R 1 . . H
H3B 0.8719 -0.0429 -0.3518 0.066 Uiso calc R 1 . . H
H3C 0.7327 -0.1137 -0.3100 0.066 Uiso calc R 1 . . H
S1 0.75716(5) 0.20720(4) 0.18066(4) 0.02909(11) Uani d . 1 . . S
F1 0.56130(14) 0.12817(13) 0.30814(11) 0.0658(4) Uani d . 1 . . F
F2 0.69659(14) -0.03200(12) 0.24689(12) 0.0649(4) Uani d . 1 . . F
F3 0.52539(13) 0.02686(12) 0.12473(11) 0.0585(3) Uani d . 1 . . F
O11 0.82191(13) 0.13343(12) 0.08232(11) 0.0384(3) Uani d . 1 . . O
O12 0.85742(13) 0.24608(13) 0.29065(11) 0.0479(4) Uani d . 1 . . O
O13 0.66623(13) 0.31371(12) 0.14929(11) 0.0397(3) Uani d . 1 . . O
C4 0.6278(2) 0.07484(19) 0.21640(17) 0.0372(4) Uani d . 1 . . C
O1 0.68198(14) 0.62088(12) 0.57166(10) 0.0406(3) Uani d . 1 . . O
N1 0.80701(14) 0.44014(13) 0.49423(12) 0.0264(3) Uani d . 1 . . N
H1 0.8211 0.3903 0.4280 0.032 Uiso calc R 1 . . H
N2 0.64656(14) 0.54022(13) 0.36927(11) 0.0247(3) Uani d . 1 . . N
H2A 0.6717 0.4784 0.3148 0.030 Uiso calc R 1 . . H
C1 0.70925(17) 0.54100(16) 0.48560(14) 0.0249(4) Uani d . 1 . . C
N11 1.04683(17) 0.33489(17) 0.80203(15) 0.0443(4) Uani d . 1 . . N
C12 1.0463(2) 0.2641(2) 0.69164(19) 0.0440(5) Uani d . 1 . . C
H12 1.1012 0.1875 0.6834 0.053 Uiso calc R 1 . . H
C13 0.97008(19) 0.29712(18) 0.58935(17) 0.0366(4) Uani d . 1 . . C
H13 0.9749 0.2445 0.5146 0.044 Uiso calc R 1 . . H
C14 0.88485(18) 0.41131(16) 0.59933(15) 0.0273(4) Uani d . 1 . . C
C15 0.8866(2) 0.48728(18) 0.71277(16) 0.0369(4) Uani d . 1 . . C
H15A 0.8344 0.5655 0.7239 0.044 Uiso calc R 1 . . H
C16 0.9673(2) 0.4449(2) 0.80916(17) 0.0453(5) Uani d . 1 . . C
H16 0.9665 0.4968 0.8849 0.054 Uiso calc R 1 . . H
N21 0.34134(15) 0.80415(13) 0.23998(12) 0.0290(3) Uani d . 1 . . N
C22 0.39556(18) 0.70308(17) 0.16774(15) 0.0298(4) Uani d . 1 . . C
H22 0.3638 0.6915 0.0856 0.036 Uiso calc R 1 . . H
C23 0.49556(18) 0.61560(16) 0.20837(14) 0.0268(4) Uani d . 1 . . C
H23 0.5292 0.5473 0.1544 0.032 Uiso calc R 1 . . H
C24 0.54559(17) 0.63065(15) 0.33099(14) 0.0221(3) Uani d . 1 . . C
C25 0.49125(17) 0.73559(16) 0.40699(15) 0.0274(4) Uani d . 1 . . C
H25 0.5216 0.7505 0.4895 0.033 Uiso calc R 1 . . H
C26 0.39121(18) 0.81690(17) 0.35664(15) 0.0309(4) Uani d . 1 . . C
H26 0.3558 0.8862 0.4085 0.037 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 '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'
C C 0.0033 0.0016 '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
O3 Ca1 O2 . 89.42(4)
O3 Ca1 O11 . 83.08(4)
O2 Ca1 O11 . 88.24(4)
O3 Ca1 O11 2_755 96.92(4)
O2 Ca1 O11 2_755 91.76(4)
O11 Ca1 O11 2_755 180
C2 O2 H2 . 109.5
O2 C2 H2B . 109.5
O2 C2 H2C . 109.5
H2B C2 H2C . 109.5
O2 C2 H2D . 109.5
H2B C2 H2D . 109.5
H2C C2 H2D . 109.5
C3 O3 H3 . 109.5
O3 C3 H3A . 109.5
O3 C3 H3B . 109.5
H3A C3 H3B . 109.5
O3 C3 H3C . 109.5
H3A C3 H3C . 109.5
H3B C3 H3C . 109.5
O13 S1 O12 . 114.92(8)
O13 S1 O11 . 114.99(7)
O12 S1 O11 . 114.24(7)
O13 S1 C4 . 104.20(8)
O12 S1 C4 . 103.04(9)
O11 S1 C4 . 103.28(8)
S1 O11 Ca1 . 153.75(8)
F3 C4 F2 . 107.80(16)
F3 C4 F1 . 108.07(15)
F2 C4 F1 . 108.13(15)
F3 C4 S1 . 111.69(13)
F2 C4 S1 . 111.16(13)
F1 C4 S1 . 109.87(13)
C1 N1 C14 . 126.53(14)
C1 N1 H1 . 116.7
C14 N1 H1 . 116.7
C1 N2 C24 . 126.11(13)
C1 N2 H2A . 116.9
C24 N2 H2A . 116.9
O1 C1 N2 . 124.02(14)
O1 C1 N1 . 123.58(15)
N2 C1 N1 . 112.40(14)
C12 N11 C16 . 115.60(16)
N11 C12 C13 . 124.31(17)
N11 C12 H12 . 117.8
C13 C12 H12 . 117.8
C12 C13 C14 . 119.08(18)
C12 C13 H13 . 120.5
C14 C13 H13 . 120.5
C15 C14 N1 . 125.20(14)
C15 C14 C13 . 117.27(16)
N1 C14 C13 . 117.53(15)
C16 C15 C14 . 118.72(17)
C16 C15 H15A . 120.6
C14 C15 H15A . 120.6
N11 C16 C15 . 124.99(18)
N11 C16 H16 . 117.5
C15 C16 H16 . 117.5
C26 N21 C22 . 115.56(13)
N21 C22 C23 . 123.95(15)
N21 C22 H22 . 118.0
C23 C22 H22 . 118.0
C22 C23 C24 . 119.40(15)
C22 C23 H23 . 120.3
C24 C23 H23 . 120.3
C23 C24 C25 . 117.36(14)
C23 C24 N2 . 117.99(13)
C25 C24 N2 . 124.64(14)
C26 C25 C24 . 118.38(15)
C26 C25 H25 . 120.8
C24 C25 H25 . 120.8
N21 C26 C25 . 125.36(15)
N21 C26 H26 . 117.3
C25 C26 H26 . 117.3
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
Ca1 O2 . 2.3384(11) y
Ca1 O3 . 2.3215(11) y
Ca1 O11 . 2.3521(11) y
O2 C2 . 1.4239(19) ?
O2 H2 . 0.82 ?
C2 H2B . 0.96 ?
C2 H2C . 0.96 ?
C2 H2D . 0.96 ?
O3 C3 . 1.4209(19) ?
O3 H3 . 0.82 ?
C3 H3A . 0.96 ?
C3 H3B . 0.96 ?
C3 H3C . 0.96 ?
S1 O13 . 1.4375(11) ?
S1 O12 . 1.4381(13) ?
S1 O11 . 1.4471(11) ?
S1 C4 . 1.818(2) ?
F1 C4 . 1.3280(19) ?
F2 C4 . 1.3252(19) ?
F3 C4 . 1.315(2) ?
O1 C1 . 1.2160(18) y
N1 C1 . 1.3834(18) y
N1 C14 . 1.3913(19) y
N1 H1 . 0.86 ?
N2 C1 . 1.3731(19) y
N2 C24 . 1.3996(18) y
N2 H2A . 0.86 ?
N11 C12 . 1.334(2) ?
N11 C16 . 1.337(2) ?
C12 C13 . 1.375(2) ?
C12 H12 . 0.93 ?
C13 C14 . 1.404(2) ?
C13 H13 . 0.93 ?
C14 C15 . 1.382(2) ?
C15 C16 . 1.379(2) ?
C15 H15A . 0.93 ?
C16 H16 . 0.93 ?
N21 C26 . 1.331(2) ?
N21 C22 . 1.3466(19) ?
C22 C23 . 1.382(2) ?
C22 H22 . 0.93 ?
C23 C24 . 1.394(2) ?
C23 H23 . 0.93 ?
C24 C25 . 1.395(2) ?
C25 C26 . 1.382(2) ?
C25 H25 . 0.93 ?
C26 H26 . 0.93 ?
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
_geom_hbond_publ_flag
N1 H1 O12 . 0.86 2.01 2.8608(18) 170 y
N2 H2A O13 . 0.86 2.27 3.1025(17) 163 y
C3 H3A O12 2_755 0.96 2.52 3.316(2) 140 y
O2 H2 N11 1_554 0.82 1.87 2.6891(18) 179 y
O3 H3 N21 2_665 0.82 1.92 2.7250(16) 167 y
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
O13 S1 O11 Ca1 . 156.19(15)
O12 S1 O11 Ca1 . 20.2(2)
C4 S1 O11 Ca1 . -90.98(18)
O3 Ca1 O11 S1 2_755 -0.18(18)
O2 Ca1 O11 S1 2_755 89.45(17)
O13 S1 C4 F3 . 59.24(14)
O12 S1 C4 F3 . 179.56(12)
O11 S1 C4 F3 . -61.25(14)
O13 S1 C4 F2 . 179.69(13)
O12 S1 C4 F2 . -60.00(14)
O11 S1 C4 F2 . 59.19(15)
O13 S1 C4 F1 . -60.66(14)
O12 S1 C4 F1 . 59.65(14)
O11 S1 C4 F1 . 178.84(12)
C24 N2 C1 O1 . 1.3(3)
C24 N2 C1 N1 . -178.88(14)
C14 N1 C1 O1 . 1.9(3)
C14 N1 C1 N2 . -177.95(14)
C16 N11 C12 C13 . -0.6(3)
N11 C12 C13 C14 . -0.8(3)
C1 N1 C14 C15 . -5.8(3)
C1 N1 C14 C13 . 175.15(16)
C12 C13 C14 C15 . 2.0(3)
C12 C13 C14 N1 . -178.86(16)
N1 C14 C15 C16 . 179.02(16)
C13 C14 C15 C16 . -1.9(3)
C12 N11 C16 C15 . 0.6(3)
C14 C15 C16 N11 . 0.6(3)
C26 N21 C22 C23 . 0.4(2)
N21 C22 C23 C24 . -0.2(3)
C22 C23 C24 C25 . -0.3(2)
C22 C23 C24 N2 . 179.86(14)
C1 N2 C24 C23 . 178.92(15)
C1 N2 C24 C25 . -0.9(3)
C23 C24 C25 C26 . 0.4(2)
N2 C24 C25 C26 . -179.70(15)
C22 N21 C26 C25 . -0.3(3)
C24 C25 C26 N21 . -0.2(3)
