#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/38/1513853.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1513853
loop_
_publ_author_name
'Vantomme, Ghislaine'
'Hafezi, Nema'
'Lehn, Jean-Marie'
_publ_section_title
;
 A light-induced reversible phase separation and its coupling to a dynamic
 library of imines
;
_journal_issue                   4
_journal_name_full               'Chemical Science'
_journal_page_first              1475
_journal_paper_doi               10.1039/c3sc53130a
_journal_volume                  5
_journal_year                    2014
_chemical_formula_moiety         'C13 H10 Ca F6 N4 O6 S2'
_chemical_formula_sum            'C13 H10 Ca F6 N4 O6 S2'
_chemical_formula_weight         536.45
_chemical_name_systematic
;
 ?
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.066(2)
_cell_angle_beta                 98.016(2)
_cell_angle_gamma                100.127(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8738(9)
_cell_length_b                   10.2258(10)
_cell_length_c                   11.1100(11)
_cell_measurement_reflns_used    5678
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.66
_cell_volume                     980.84(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  triumph
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15522
_diffrn_reflns_theta_full        30.30
_diffrn_reflns_theta_max         30.30
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  0.9692
_exptl_absorpt_correction_T_min  0.8334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0276P)²+3.6407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1409
_reflns_number_gt                4438
_reflns_number_total             5770
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3sc53130a.txt
_cod_data_source_block           jmlgv120116
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1   '
_cod_database_code               1513853
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.2618(4) 0.2948(4) 0.1639(3) 0.0272(7) Uani 1 1 d .
H1 H 0.2185 0.3734 0.1606 0.033 Uiso 1 1 calc R
C2 C 0.3117(5) 0.2498(4) 0.0608(4) 0.0363(9) Uani 1 1 d .
H2 H 0.3013 0.2951 -0.0122 0.044 Uiso 1 1 calc R
C3 C 0.3777(5) 0.1360(4) 0.0666(4) 0.0378(10) Uani 1 1 d .
H3 H 0.4157 0.1036 -0.0024 0.045 Uiso 1 1 calc R
C4 C 0.3878(5) 0.0711(4) 0.1722(4) 0.0321(8) Uani 1 1 d .
H4 H 0.4318 -0.0071 0.1780 0.038 Uiso 1 1 calc R
C5 C 0.3314(4) 0.1232(3) 0.2713(3) 0.0227(7) Uani 1 1 d .
C6 C 0.2411(4) 0.0218(3) 0.5550(3) 0.0215(7) Uani 1 1 d .
H6 H 0.2832 -0.0573 0.5620 0.026 Uiso 1 1 calc R
C7 C 0.1544(4) 0.0637(3) 0.6456(3) 0.0226(7) Uani 1 1 d .
C8 C 0.1269(5) -0.0130(4) 0.7438(3) 0.0306(8) Uani 1 1 d .
H8 H 0.1676 -0.0925 0.7537 0.037 Uiso 1 1 calc R
C9 C 0.0396(5) 0.0278(4) 0.8268(4) 0.0368(9) Uani 1 1 d .
H9 H 0.0197 -0.0230 0.8947 0.044 Uiso 1 1 calc R
C10 C -0.0177(5) 0.1429(4) 0.8096(4) 0.0340(9) Uani 1 1 d .
H10 H -0.0794 0.1725 0.8646 0.041 Uiso 1 1 calc R
C11 C 0.0157(4) 0.2152(4) 0.7107(4) 0.0290(8) Uani 1 1 d .
H11 H -0.0241 0.2950 0.6998 0.035 Uiso 1 1 calc R
C12 C 0.5706(5) 0.3383(4) 0.7833(4) 0.0290(8) Uani 1 1 d .
C13 C -0.1595(5) 0.4070(4) 0.1668(3) 0.0295(8) Uani 1 1 d .
N1 N 0.2708(3) 0.2338(3) 0.2688(3) 0.0215(6) Uani 1 1 d .
N2 N 0.3363(4) 0.0560(3) 0.3778(3) 0.0259(6) Uani 1 1 d .
N3 N 0.2594(3) 0.0950(3) 0.4646(3) 0.0211(6) Uani 1 1 d .
N4 N 0.1013(3) 0.1785(3) 0.6295(3) 0.0226(6) Uani 1 1 d .
Ca1 Ca 0.20521(7) 0.33023(6) 0.46713(6) 0.01562(14) Uani 1 1 d .
F1 F 0.4668(3) 0.2293(3) 0.7938(3) 0.0490(7) Uani 1 1 d .
F2 F 0.5157(3) 0.4409(3) 0.8206(3) 0.0457(7) Uani 1 1 d .
F3 F 0.6993(3) 0.3309(3) 0.8567(2) 0.0505(7) Uani 1 1 d .
F4 F -0.2759(4) 0.4571(3) 0.1103(2) 0.0536(8) Uani 1 1 d .
F5 F -0.1569(3) 0.2920(3) 0.1077(2) 0.0444(7) Uani 1 1 d .
F6 F -0.0291(3) 0.4893(3) 0.1546(3) 0.0490(7) Uani 1 1 d .
O1 O 0.4587(3) 0.3591(3) 0.5608(2) 0.0277(6) Uani 1 1 d .
O2 O 0.6572(3) 0.2251(2) 0.6034(3) 0.0306(6) Uani 1 1 d .
O3 O -0.0407(3) 0.3287(3) 0.3683(2) 0.0258(5) Uani 1 1 d .
O4 O -0.3193(3) 0.2925(3) 0.3218(3) 0.0336(6) Uani 1 1 d .
O5 O 0.1715(3) 0.4834(2) 0.6234(2) 0.0287(6) Uani 1 1 d .
O6 O 0.2767(3) 0.5346(2) 0.3710(2) 0.0222(5) Uani 1 1 d .
S1 S 0.60632(9) 0.34731(7) 0.62589(7) 0.01739(16) Uani 1 1 d .
S2 S -0.17756(9) 0.38307(8) 0.32601(7) 0.01852(17) Uani 1 1 d .
H2N H 0.360(5) -0.023(4) 0.375(4) 0.029(11) Uiso 1 1 d .
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'
Ca Ca 0.2262 0.3064 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 C2 123.7(3) . .
N1 C1 H1 118.2 . .
C2 C1 H1 118.2 . .
C1 C2 C3 118.1(4) . .
C1 C2 H2 121.0 . .
C3 C2 H2 121.0 . .
C4 C3 C2 119.6(4) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C3 C4 C5 118.1(3) . .
C3 C4 H4 121.0 . .
C5 C4 H4 121.0 . .
N1 C5 N2 117.9(3) . .
N1 C5 C4 123.4(3) . .
N2 C5 C4 118.7(3) . .
N3 C6 C7 117.8(3) . .
N3 C6 H6 121.1 . .
C7 C6 H6 121.1 . .
N4 C7 C8 122.3(3) . .
N4 C7 C6 117.1(3) . .
C8 C7 C6 120.7(3) . .
C9 C8 C7 119.2(4) . .
C9 C8 H8 120.4 . .
C7 C8 H8 120.4 . .
C10 C9 C8 118.9(4) . .
C10 C9 H9 120.6 . .
C8 C9 H9 120.6 . .
C9 C10 C11 118.9(4) . .
C9 C10 H10 120.6 . .
C11 C10 H10 120.6 . .
N4 C11 C10 123.5(4) . .
N4 C11 H11 118.3 . .
C10 C11 H11 118.3 . .
F2 C12 F3 108.7(3) . .
F2 C12 F1 107.5(3) . .
F3 C12 F1 107.9(3) . .
F2 C12 S1 112.3(3) . .
F3 C12 S1 110.6(3) . .
F1 C12 S1 109.8(3) . .
F4 C13 F5 107.8(3) . .
F4 C13 F6 107.4(3) . .
F5 C13 F6 107.0(3) . .
F4 C13 S2 111.9(3) . .
F5 C13 S2 110.8(3) . .
F6 C13 S2 111.8(3) . .
C5 N1 C1 117.1(3) . .
C5 N1 Ca1 118.8(2) . .
C1 N1 Ca1 123.7(2) . .
N3 N2 C5 117.6(3) . .
N3 N2 H2N 121(3) . .
C5 N2 H2N 118(3) . .
C6 N3 N2 118.7(3) . .
C6 N3 Ca1 121.6(2) . .
N2 N3 Ca1 118.4(2) . .
C11 N4 C7 117.3(3) . .
C11 N4 Ca1 123.9(2) . .
C7 N4 Ca1 118.1(2) . .
O3 Ca1 O1 172.88(10) . .
O3 Ca1 O5 91.39(9) . .
O1 Ca1 O5 85.67(10) . .
O3 Ca1 O6 85.69(9) . .
O1 Ca1 O6 87.44(9) . .
O5 Ca1 O6 81.01(9) . .
O3 Ca1 N3 109.38(9) . .
O1 Ca1 N3 77.17(9) . .
O5 Ca1 N3 133.90(10) . .
O6 Ca1 N3 139.17(9) . .
O3 Ca1 N1 88.37(9) . .
O1 Ca1 N1 92.41(10) . .
O5 Ca1 N1 161.94(9) . .
O6 Ca1 N1 80.97(9) . .
N3 Ca1 N1 62.49(9) . .
O3 Ca1 N4 91.88(10) . .
O1 Ca1 N4 93.73(10) . .
O5 Ca1 N4 76.44(9) . .
O6 Ca1 N4 157.25(9) . .
N3 Ca1 N4 62.64(9) . .
N1 Ca1 N4 121.62(9) . .
S1 O1 Ca1 167.31(17) . .
S2 O3 Ca1 156.65(16) . .
S2 O5 Ca1 152.24(17) 2_566 .
S1 O6 Ca1 144.35(15) 2_666 .
O2 S1 O1 115.84(17) . .
O2 S1 O6 114.98(16) . 2_666
O1 S1 O6 114.02(15) . 2_666
O2 S1 C12 102.68(17) . .
O1 S1 C12 103.22(17) . .
O6 S1 C12 103.70(17) 2_666 .
O4 S2 O5 116.87(17) . 2_566
O4 S2 O3 114.56(17) . .
O5 S2 O3 113.21(16) 2_566 .
O4 S2 C13 104.19(19) . .
O5 S2 C13 103.39(17) 2_566 .
O3 S2 C13 102.24(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.340(5) .
C1 C2 1.377(5) .
C1 H1 0.9500 .
C2 C3 1.391(6) .
C2 H2 0.9500 .
C3 C4 1.369(6) .
C3 H3 0.9500 .
C4 C5 1.396(5) .
C4 H4 0.9500 .
C5 N1 1.335(4) .
C5 N2 1.389(5) .
C6 N3 1.285(4) .
C6 C7 1.446(5) .
C6 H6 0.9500 .
C7 N4 1.348(4) .
C7 C8 1.391(5) .
C8 C9 1.382(6) .
C8 H8 0.9500 .
C9 C10 1.371(6) .
C9 H9 0.9500 .
C10 C11 1.383(6) .
C10 H10 0.9500 .
C11 N4 1.341(5) .
C11 H11 0.9500 .
C12 F2 1.310(4) .
C12 F3 1.323(5) .
C12 F1 1.335(4) .
C12 S1 1.823(4) .
C13 F4 1.323(4) .
C13 F5 1.331(4) .
C13 F6 1.333(5) .
C13 S2 1.820(4) .
N1 Ca1 2.563(3) .
N2 N3 1.344(4) .
N2 H2N 0.87(4) .
N3 Ca1 2.534(3) .
N4 Ca1 2.583(3) .
Ca1 O3 2.299(3) .
Ca1 O1 2.306(3) .
Ca1 O5 2.381(2) .
Ca1 O6 2.408(2) .
O1 S1 1.433(3) .
O2 S1 1.427(2) .
O3 S2 1.449(2) .
O4 S2 1.419(3) .
O5 S2 1.447(2) 2_566
O6 S1 1.443(2) 2_666
S1 O6 1.443(2) 2_666
S2 O5 1.447(2) 2_566
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N O2 0.87(4) 2.07(4) 2.900(4) 159(4) 2_656
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_site_symmetry_4
N1 C1 C2 C3 -1.2(7) .
C1 C2 C3 C4 1.5(7) .
C2 C3 C4 C5 -0.5(7) .
C3 C4 C5 N1 -1.1(6) .
C3 C4 C5 N2 178.0(4) .
N3 C6 C7 N4 -1.2(5) .
N3 C6 C7 C8 178.2(3) .
N4 C7 C8 C9 1.3(6) .
C6 C7 C8 C9 -178.1(4) .
C7 C8 C9 C10 0.2(6) .
C8 C9 C10 C11 -1.0(6) .
C9 C10 C11 N4 0.4(6) .
N2 C5 N1 C1 -177.6(3) .
C4 C5 N1 C1 1.5(5) .
N2 C5 N1 Ca1 8.6(4) .
C4 C5 N1 Ca1 -172.3(3) .
C2 C1 N1 C5 -0.3(6) .
C2 C1 N1 Ca1 173.2(3) .
N1 C5 N2 N3 9.7(5) .
C4 C5 N2 N3 -169.4(3) .
C7 C6 N3 N2 -178.3(3) .
C7 C6 N3 Ca1 14.5(4) .
C5 N2 N3 C6 169.0(3) .
C5 N2 N3 Ca1 -23.5(4) .
C10 C11 N4 C7 1.1(6) .
C10 C11 N4 Ca1 -168.8(3) .
C8 C7 N4 C11 -1.9(5) .
C6 C7 N4 C11 177.5(3) .
C8 C7 N4 Ca1 168.6(3) .
C6 C7 N4 Ca1 -12.0(4) .
C6 N3 Ca1 O3 -96.3(3) .
N2 N3 Ca1 O3 96.5(3) .
C6 N3 Ca1 O1 86.6(3) .
N2 N3 Ca1 O1 -80.6(3) .
C6 N3 Ca1 O5 15.7(3) .
N2 N3 Ca1 O5 -151.5(2) .
C6 N3 Ca1 O6 157.1(2) .
N2 N3 Ca1 O6 -10.0(3) .
C6 N3 Ca1 N1 -173.7(3) .
N2 N3 Ca1 N1 19.1(2) .
C6 N3 Ca1 N4 -14.5(3) .
N2 N3 Ca1 N4 178.3(3) .
C5 N1 Ca1 O3 -127.0(3) .
C1 N1 Ca1 O3 59.7(3) .
C5 N1 Ca1 O1 60.1(3) .
C1 N1 Ca1 O1 -113.2(3) .
C5 N1 Ca1 O5 143.5(3) .
C1 N1 Ca1 O5 -29.8(5) .
C5 N1 Ca1 O6 147.2(3) .
C1 N1 Ca1 O6 -26.2(3) .
C5 N1 Ca1 N3 -14.1(2) .
C1 N1 Ca1 N3 172.6(3) .
C5 N1 Ca1 N4 -35.7(3) .
C1 N1 Ca1 N4 150.9(3) .
C11 N4 Ca1 O3 -66.2(3) .
C7 N4 Ca1 O3 124.0(3) .
C11 N4 Ca1 O1 109.4(3) .
C7 N4 Ca1 O1 -60.4(3) .
C11 N4 Ca1 O5 24.8(3) .
C7 N4 Ca1 O5 -145.0(3) .
C11 N4 Ca1 O6 17.1(4) .
C7 N4 Ca1 O6 -152.7(2) .
C11 N4 Ca1 N3 -177.1(3) .
C7 N4 Ca1 N3 13.1(2) .
C11 N4 Ca1 N1 -155.5(3) .
C7 N4 Ca1 N1 34.7(3) .
O5 Ca1 O1 S1 110.7(8) .
O6 Ca1 O1 S1 -168.1(8) .
N3 Ca1 O1 S1 -26.2(8) .
N1 Ca1 O1 S1 -87.3(8) .
N4 Ca1 O1 S1 34.6(8) .
O5 Ca1 O3 S2 34.6(4) .
O6 Ca1 O3 S2 -46.2(4) .
N3 Ca1 O3 S2 172.7(4) .
N1 Ca1 O3 S2 -127.3(4) .
N4 Ca1 O3 S2 111.1(4) .
O3 Ca1 O5 S2 -87.3(4) 2_566
O1 Ca1 O5 S2 86.2(4) 2_566
O6 Ca1 O5 S2 -1.9(4) 2_566
N3 Ca1 O5 S2 153.8(3) 2_566
N1 Ca1 O5 S2 1.7(6) 2_566
N4 Ca1 O5 S2 -178.9(4) 2_566
O3 Ca1 O6 S1 162.8(3) 2_666
O1 Ca1 O6 S1 -15.4(3) 2_666
O5 Ca1 O6 S1 70.7(3) 2_666
N3 Ca1 O6 S1 -82.3(3) 2_666
N1 Ca1 O6 S1 -108.2(3) 2_666
N4 Ca1 O6 S1 78.2(4) 2_666
Ca1 O1 S1 O2 42.5(9) .
Ca1 O1 S1 O6 179.3(8) 2_666
Ca1 O1 S1 C12 -68.9(8) .
F2 C12 S1 O2 -177.3(3) .
F3 C12 S1 O2 61.1(3) .
F1 C12 S1 O2 -57.8(3) .
F2 C12 S1 O1 -56.5(3) .
F3 C12 S1 O1 -178.1(3) .
F1 C12 S1 O1 62.9(3) .
F2 C12 S1 O6 62.7(3) 2_666
F3 C12 S1 O6 -58.9(3) 2_666
F1 C12 S1 O6 -177.9(3) 2_666
Ca1 O3 S2 O4 -145.0(4) .
Ca1 O3 S2 O5 -7.5(5) 2_566
Ca1 O3 S2 C13 103.0(4) .
F4 C13 S2 O4 60.5(3) .
F5 C13 S2 O4 -59.8(3) .
F6 C13 S2 O4 -179.1(3) .
F4 C13 S2 O5 -62.2(3) 2_566
F5 C13 S2 O5 177.5(3) 2_566
F6 C13 S2 O5 58.3(3) 2_566
F4 C13 S2 O3 -180.0(3) .
F5 C13 S2 O3 59.7(3) .
F6 C13 S2 O3 -59.5(3) .
