#------------------------------------------------------------------------------
#$Date: 2019-11-24 04:55:20 +0100 (dom 24 de nov de 2019) $
#$Revision: 236872 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/91/7059121.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_7059121
loop_
_publ_author_name
'Karmakar, Anirban'
'Hazra, Susanta'
'Rúbio, Guilherme M. D. M.'
'Guedes da Silva, M. Fátima C.'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Packing polymorphism in 3-amino-2-pyrazinecarboxylate based tin(ii)
 complexes and their catalytic activity towards cyanosilylation of
 aldehydes
;
_journal_issue                   21
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17513
_journal_paper_doi               10.1039/C8NJ03805H
_journal_volume                  42
_journal_year                    2018
_chemical_formula_sum            'C10 H8 N6 O4 Sn'
_chemical_formula_weight         394.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2yc'
_space_group_name_H-M_alt        'I 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2018-07-30 deposited with the CCDC.
2018-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.631(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9805(19)
_cell_length_b                   9.1305(9)
_cell_length_c                   12.6134(13)
_cell_measurement_reflns_used    7217
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.87
_cell_volume                     1233.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12182
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_min         2.871
_exptl_absorpt_coefficient_mu    2.101
_exptl_absorpt_correction_T_max  0.6
_exptl_absorpt_correction_T_min  0.5
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.127
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.980
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0253
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0334P)²+1.6077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0594
_refine_ls_wR_factor_ref         0.0613
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1151
_reflns_number_total             1261
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj03805h2.cif
_cod_data_source_block           Sn1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_space_group_crystal_system' value 'Monoclinic' was
changed to 'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      I2/c
_cod_database_code               7059121
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.544
_shelx_estimated_absorpt_t_max   0.704
_shelxl_version_number           2014-3
_shelx_res_file
;
TITL AK471 in I2/c
CELL  0.71073  11.9805   9.1305  12.6134   90.000  116.631   90.000
ZERR     4.00   0.0019   0.0009   0.0013    0.000    0.009    0.000
LATT   2
SYMM  - X,   Y, 1/2 - Z
SFAC  C    H    N    O    SN
UNIT  40   32   24   16   4
MERG   2
EQIV $1 x, -y+1, z-1/2
HTAB N3 O1_$1
HTAB N3 O2
EQIV $2 x-1/2, y+1/2, z-1/2
HTAB C1 O2_$2
FMAP   2
PLAN    5
SIZE     0.180   0.240   0.330
ACTA
HTAB    2.00000
BOND   $H
CONF
L.S.   5
TEMP    23.00
WGHT    0.033400    1.607700
FVAR       0.09262
SN1   5    0.000000    0.850169    0.250000    10.50000    0.02979    0.02695 =
         0.02979    0.00000    0.01389    0.00000
O1    4    0.140468    0.681295    0.303763    11.00000    0.03014    0.03395 =
         0.02215    0.00315    0.01150    0.00338
O2    4    0.250895    0.516990    0.260919    11.00000    0.03589    0.03814 =
         0.03376    0.00647    0.01379    0.00987
N1    3    0.011958    0.756503    0.077587    11.00000    0.02861    0.03121 =
         0.02622    0.00245    0.01185    0.00038
N2    3    0.061736    0.649163   -0.101181    11.00000    0.04703    0.04865 =
         0.02669    0.00075    0.01831    0.00283
N3    3    0.216303    0.500377    0.030303    11.00000    0.04292    0.04516 =
         0.03215   -0.00328    0.01910    0.00833
AFIX   3
H3A   2    0.229113    0.469587   -0.027547    11.00000   -1.20000
H3B   2    0.260213    0.466727    0.100542    11.00000   -1.20000
AFIX   0
C1    1   -0.053130    0.803111   -0.033574    11.00000    0.03552    0.03788 =
         0.03248    0.00760    0.01209    0.00580
AFIX  43
H1    2   -0.115662    0.872843   -0.051869    11.00000   -1.20000
AFIX   0
C2    1   -0.026614    0.746644   -0.121215    11.00000    0.04703    0.04985 =
         0.02606    0.00902    0.01291    0.00383
AFIX  43
H2    2   -0.073620    0.779123   -0.198592    11.00000   -1.20000
AFIX   0
C3    1    0.126974    0.600948    0.010900    11.00000    0.03153    0.03266 =
         0.02889   -0.00176    0.01408   -0.00417
C4    1    0.100861    0.656202    0.102780    11.00000    0.02387    0.02593 =
         0.02475   -0.00049    0.01063   -0.00397
C5    1    0.169939    0.611765    0.230597    11.00000    0.02380    0.02770 =
         0.02556    0.00215    0.01053   -0.00298
HKLF    4  1.0  0.00  0.00  1.00  0.00  1.00  0.00 -1.00  0.00 -1.00

REM  AK471 in I2/c
REM R1 =  0.0253 for    1151 Fo > 4sig(Fo)  and  0.0298 for all    1261 data
REM     96 parameters refined using      0 restraints

END

WGHT      0.0333      1.6780

REM Instructions for potential hydrogen bonds
HTAB N3 O1_$1
HTAB N3 O2
HTAB C1 O2_$2

REM Highest difference peak  0.980,  deepest hole -0.294,  1-sigma level  0.112
Q1    1   0.0000  0.5512 -0.2500  10.50000  0.05    0.98
Q2    1   0.0014  0.8522  0.3185  11.00000  0.05    0.70
Q3    1   0.0656  0.8258  0.3262  11.00000  0.05    0.54
Q4    1   0.1403  0.6427  0.1679  11.00000  0.05    0.49
Q5    1   0.1156  0.6236  0.0591  11.00000  0.05    0.45
;
_shelx_res_checksum              99865
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Sn1 Sn 0.0000 0.85017(3) 0.2500 0.02864(12) Uani 1 2 d S T P
O1 O 0.1405(2) 0.6813(2) 0.30376(18) 0.0288(4) Uani 1 1 d . . .
O2 O 0.2509(2) 0.5170(2) 0.2609(2) 0.0366(5) Uani 1 1 d . . .
N1 N 0.0120(2) 0.7565(3) 0.0776(2) 0.0288(5) Uani 1 1 d . . .
N2 N 0.0617(3) 0.6492(3) -0.1012(2) 0.0401(7) Uani 1 1 d . . .
N3 N 0.2163(3) 0.5004(3) 0.0303(3) 0.0392(6) Uani 1 1 d . . .
H3A H 0.2291 0.4696 -0.0275 0.047 Uiso 1 1 d R U .
H3B H 0.2602 0.4667 0.1005 0.047 Uiso 1 1 d R U .
C1 C -0.0531(3) 0.8031(4) -0.0336(3) 0.0365(7) Uani 1 1 d . . .
H1 H -0.1157 0.8728 -0.0519 0.044 Uiso 1 1 calc R U .
C2 C -0.0266(3) 0.7466(4) -0.1212(3) 0.0423(8) Uani 1 1 d . . .
H2 H -0.0736 0.7791 -0.1986 0.051 Uiso 1 1 calc R U .
C3 C 0.1270(3) 0.6009(3) 0.0109(3) 0.0308(6) Uani 1 1 d . . .
C4 C 0.1009(3) 0.6562(3) 0.1028(3) 0.0250(6) Uani 1 1 d . . .
C5 C 0.1699(3) 0.6118(3) 0.2306(3) 0.0259(6) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Sn1 0.0298(2) 0.02695(16) 0.02979(18) 0.000 0.01389(14) 0.000
O1 0.0301(12) 0.0339(10) 0.0221(10) 0.0032(8) 0.0115(9) 0.0034(8)
O2 0.0359(13) 0.0381(12) 0.0338(12) 0.0065(9) 0.0138(10) 0.0099(9)
N1 0.0286(14) 0.0312(12) 0.0262(13) 0.0025(10) 0.0118(11) 0.0004(10)
N2 0.0470(19) 0.0487(17) 0.0267(14) 0.0007(11) 0.0183(13) 0.0028(13)
N3 0.0429(17) 0.0452(15) 0.0322(14) -0.0033(12) 0.0191(13) 0.0083(12)
C1 0.036(2) 0.0379(16) 0.0325(16) 0.0076(13) 0.0121(15) 0.0058(14)
C2 0.047(2) 0.0498(19) 0.0261(16) 0.0090(14) 0.0129(16) 0.0038(16)
C3 0.0315(18) 0.0327(14) 0.0289(15) -0.0018(12) 0.0141(14) -0.0042(12)
C4 0.0239(15) 0.0259(13) 0.0248(14) -0.0005(11) 0.0106(12) -0.0040(11)
C5 0.0238(16) 0.0277(13) 0.0256(14) 0.0022(11) 0.0105(13) -0.0030(11)
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'
Sn Sn -0.6537 1.4246 '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
O1 Sn1 O1 88.66(11) 2 .
O1 Sn1 N1 79.36(8) 2 .
O1 Sn1 N1 71.03(8) . .
O1 Sn1 N1 71.03(8) 2 2
O1 Sn1 N1 79.36(8) . 2
N1 Sn1 N1 138.25(11) . 2
C5 O1 Sn1 123.45(18) . .
C4 N1 C1 120.0(3) . .
C4 N1 Sn1 113.29(18) . .
C1 N1 Sn1 126.5(2) . .
C2 N2 C3 117.4(3) . .
C3 N3 H3A 120.0 . .
C3 N3 H3B 120.0 . .
H3A N3 H3B 120.0 . .
N1 C1 C2 119.2(3) . .
N1 C1 H1 120.4 . .
C2 C1 H1 120.4 . .
N2 C2 C1 123.5(3) . .
N2 C2 H2 118.2 . .
C1 C2 H2 118.2 . .
N2 C3 N3 117.0(3) . .
N2 C3 C4 120.2(3) . .
N3 C3 C4 122.8(3) . .
N1 C4 C3 119.6(3) . .
N1 C4 C5 116.1(2) . .
C3 C4 C5 124.3(3) . .
O2 C5 O1 123.7(3) . .
O2 C5 C4 120.3(3) . .
O1 C5 C4 116.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sn1 O1 2.156(2) 2
Sn1 O1 2.156(2) .
Sn1 N1 2.400(2) .
Sn1 N1 2.400(2) 2
O1 C5 1.293(4) .
O2 C5 1.226(4) .
N1 C4 1.331(4) .
N1 C1 1.332(4) .
N2 C2 1.318(5) .
N2 C3 1.346(4) .
N3 C3 1.347(4) .
N3 H3A 0.8576 .
N3 H3B 0.8592 .
C1 C2 1.380(5) .
C1 H1 0.9300 .
C2 H2 0.9300 .
C3 C4 1.421(4) .
C4 C5 1.501(4) .
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
N3 H3A O1 0.86 2.35 3.068(3) 141.4 6_565
N3 H3B O2 0.86 2.13 2.752(4) 129.4 .
C1 H1 O2 0.93 2.55 3.254(4) 133.3 3_454
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
C4 N1 C1 C2 -0.3(5)
Sn1 N1 C1 C2 173.9(2)
C3 N2 C2 C1 1.5(5)
N1 C1 C2 N2 -0.9(5)
C2 N2 C3 N3 179.4(3)
C2 N2 C3 C4 -0.8(5)
C1 N1 C4 C3 0.9(4)
Sn1 N1 C4 C3 -174.1(2)
C1 N1 C4 C5 179.4(3)
Sn1 N1 C4 C5 4.4(3)
N2 C3 C4 N1 -0.3(4)
N3 C3 C4 N1 179.4(3)
N2 C3 C4 C5 -178.7(3)
N3 C3 C4 C5 1.1(5)
Sn1 O1 C5 O2 179.0(2)
Sn1 O1 C5 C4 0.6(3)
N1 C4 C5 O2 178.0(3)
C3 C4 C5 O2 -3.6(4)
N1 C4 C5 O1 -3.6(4)
C3 C4 C5 O1 174.8(3)
