#------------------------------------------------------------------------------
#$Date: 2020-04-21 02:02:28 +0300 (Tue, 21 Apr 2020) $
#$Revision: 250959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/78/1557831.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_1557831
loop_
_publ_author_name
'Sessler, Jonathan L.'
'Guo, Chenxing'
'Wang, Hu'
'Lynch, Vincent'
'Ji, Xiaofan'
'Page, Zachariah A.'
_publ_section_title
;
 Molecular recognition of pyrazine N,N’-dioxide using aryl extended
 calix[4]pyrroles
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC01496F
_journal_year                    2020
_chemical_formula_moiety         'C4 H4 N2 O2'
_chemical_formula_sum            'C4 H4 N2 O2'
_chemical_formula_weight         112.09
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-02-20 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.866(3)
_cell_length_b                   11.883(3)
_cell_length_c                   6.3933(15)
_cell_measurement_reflns_used    708
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.3
_cell_measurement_theta_min      3.43
_cell_volume                     901.5(4)
_computing_cell_refinement       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_collection       'Apex II release 2010, Bruker AXS, Inc.'
_computing_data_reduction        'Apex II release 2010, Bruker AXS, Inc.'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'SHELXL-2016/6, Sheldrick, G. M.'
_computing_structure_refinement  'Shelxl-2016/6, Sheldrick, G. M.'
_computing_structure_solution
;

Sheldrick, G. M. (2015).  SHELXT.  Acta Cryst. A71, 3-8.

;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius Kappa CCD with a Bruker Apex II CCD'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_unetI/netI     0.0704
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6876
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.332
_diffrn_reflns_theta_min         3.429
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS. G. M. Sheldrick
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         1170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0448
_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/[\s^2^(Fo^2^)+(0.0236P)^2^+0.4229P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                709
_reflns_number_total             1170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01496f3.cif
_cod_data_source_block           shelx_CCDC3
_cod_original_cell_volume        901.4(4)
_cod_database_code               1557831
_shelx_shelxl_version_number     2016/6
_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   0.944
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_file
;
TITL shelxt_a.res in Pnma colorless needle
    shelx.res
    created by SHELXL-2016/6 at 16:48:13 on 11-Apr-2019
rem isor .01 0.02
CELL 0.71073 11.8658 11.8827 6.3933 90 90 90
ZERR 8 0.0027 0.0027 0.0015 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,-Z
SYMM 0.5+X,0.5-Y,0.5-Z
SFAC C H N O
UNIT 32 32 16 16

L.S. 10
PLAN  20
TEMP -173
BOND $H
CONF
size .43 .16 .07
LIST 4
fmap 2
acta
MERG 2
REM <olex2.extras>
REM <HklSrc "%.\\NN-dioxidefinal.hkl">
REM </olex2.extras>

WGHT    0.023600    0.422900
FVAR       0.10222
C1    1    0.482641    0.250000    0.495120    10.50000    0.00966    0.01571 =
         0.01332    0.00000   -0.00179    0.00000
AFIX  43
H1    2    0.562159    0.250000    0.512414    10.50000   -1.20000
AFIX   0
C2    1    0.415155    0.250000    0.666205    10.50000    0.01536    0.01612 =
         0.01174    0.00000   -0.00208    0.00000
AFIX  43
H2    2    0.447862    0.250000    0.801833    10.50000   -1.20000
AFIX   0
C3    1    0.256267    0.250000    0.449989    10.50000    0.01362    0.01794 =
         0.01102    0.00000   -0.00161    0.00000
AFIX  43
H3    2    0.176749    0.250000    0.432697    10.50000   -1.20000
AFIX   0
C4    1    0.324279    0.250000    0.278573    10.50000    0.01125    0.01549 =
         0.01112    0.00000   -0.00214    0.00000
AFIX  43
H4    2    0.291689    0.250000    0.142848    10.50000   -1.20000
AFIX   0

C5    1    0.612520    0.491009   -0.023949    11.00000    0.01268    0.01364 =
         0.01388    0.00187    0.00237    0.00110
AFIX  43
H5    2    0.691768    0.485515   -0.042456    11.00000   -1.20000
AFIX   0
C6    1    0.544210    0.494125   -0.194230    11.00000    0.01273    0.01441 =
         0.01176    0.00065    0.00335   -0.00020
AFIX  43
H6    2    0.576077    0.489089   -0.330224    11.00000   -1.20000
AFIX   0

N1    3    0.438194    0.250000    0.299275    10.50000    0.01171    0.01352 =
         0.00813    0.00000    0.00184    0.00000
N2    3    0.300997    0.250000    0.645548    10.50000    0.01093    0.02089 =
         0.00932    0.00000    0.00162    0.00000
N3    3    0.569201    0.495632    0.172277    11.00000    0.01178    0.01547 =
         0.01099    0.00061   -0.00276   -0.00128
O1    4    0.502472    0.250000    0.134401    10.50000    0.01484    0.02312 =
         0.00823    0.00000    0.00477    0.00000
O2    4    0.235860    0.250000    0.807615    10.50000    0.01867    0.04958 =
         0.00826    0.00000    0.00658    0.00000
O3    4    0.634360    0.489075    0.335214    11.00000    0.01415    0.03245 =
         0.00955    0.00087   -0.00541    0.00042
HKLF 4




REM  shelxt_a.res in Pnma colorless needle
REM R1 =  0.0448 for     709 Fo > 4sig(Fo)  and  0.0860 for all    1170 data
REM     85 parameters refined using      0 restraints

END

WGHT      0.0236      0.4229

REM Highest difference peak  0.258,  deepest hole -0.344,  1-sigma level  0.063
Q1    1   0.5816  0.2500  0.1420  10.50000  0.05    0.26
Q2    1   0.4419  0.2910  0.5572  11.00000  0.05    0.24
Q3    1   0.3705  0.2500  0.6579  10.50000  0.05    0.19
Q4    1   0.5989  0.5122  0.0744  11.00000  0.05    0.19
Q5    1   0.6581  0.5786  0.3891  11.00000  0.05    0.19
Q6    1   0.2763  0.2500  0.5485  10.50000  0.05    0.18
Q7    1   0.6405  0.4186  0.3456  11.00000  0.05    0.18
Q8    1   0.4880  0.4589 -0.1863  11.00000  0.05    0.17
Q9    1   0.4385  0.2967  0.7306  11.00000  0.05    0.17
Q10   1   0.2044  0.3012  0.0501  11.00000  0.05    0.17
Q11   1   0.5785  0.2660  0.4263  11.00000  0.05    0.17
Q12   1   0.3824  0.2759  0.2889  11.00000  0.05    0.16
Q13   1   0.5704  0.4539 -0.1023  11.00000  0.05    0.16
Q14   1   0.5983  0.5299  0.4415  11.00000  0.05    0.16
Q15   1   0.7406  0.4470  0.0267  11.00000  0.05    0.16
Q16   1   0.4953  0.5203 -0.1630  11.00000  0.05    0.15
Q17   1   0.4631  0.2934  0.3997  11.00000  0.05    0.15
Q18   1   0.2614  0.2500  0.9475  10.50000  0.05    0.15
Q19   1   0.5782  0.5848 -0.4691  11.00000  0.05    0.15
Q20   1   0.5655  0.4345  0.3353  11.00000  0.05    0.15
;
_shelx_res_checksum              44778
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4826(2) 0.250000 0.4951(4) 0.0129(6) Uani 1 2 d S T P . .
H1 H 0.562159 0.250000 0.512414 0.015 Uiso 1 2 calc R U P . .
C2 C 0.4152(2) 0.250000 0.6662(4) 0.0144(6) Uani 1 2 d S T P . .
H2 H 0.447862 0.250000 0.801833 0.017 Uiso 1 2 calc R U P . .
C3 C 0.2563(2) 0.250000 0.4500(4) 0.0142(6) Uani 1 2 d S T P . .
H3 H 0.176749 0.250000 0.432697 0.017 Uiso 1 2 calc R U P . .
C4 C 0.3243(2) 0.250000 0.2786(4) 0.0126(6) Uani 1 2 d S T P . .
H4 H 0.291689 0.250000 0.142848 0.015 Uiso 1 2 calc R U P . .
C5 C 0.61252(16) 0.49101(15) -0.0239(3) 0.0134(4) Uani 1 1 d . . . . .
H5 H 0.691768 0.485515 -0.042456 0.016 Uiso 1 1 calc R U . . .
C6 C 0.54421(15) 0.49413(14) -0.1942(3) 0.0130(4) Uani 1 1 d . . . . .
H6 H 0.576077 0.489089 -0.330224 0.016 Uiso 1 1 calc R U . . .
N1 N 0.43819(18) 0.250000 0.2993(3) 0.0111(5) Uani 1 2 d S T P . .
N2 N 0.30100(18) 0.250000 0.6455(3) 0.0137(5) Uani 1 2 d S T P . .
N3 N 0.56920(13) 0.49563(12) 0.1723(2) 0.0127(4) Uani 1 1 d . . . . .
O1 O 0.50247(15) 0.250000 0.1344(3) 0.0154(4) Uani 1 2 d S T P . .
O2 O 0.23586(16) 0.250000 0.8076(3) 0.0255(5) Uani 1 2 d S T P . .
O3 O 0.63436(11) 0.48907(11) 0.3352(2) 0.0187(4) 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
C1 0.0097(13) 0.0157(13) 0.0133(14) 0.000 -0.0018(10) 0.000
C2 0.0154(14) 0.0161(13) 0.0117(13) 0.000 -0.0021(12) 0.000
C3 0.0136(13) 0.0179(13) 0.0110(13) 0.000 -0.0016(11) 0.000
C4 0.0113(13) 0.0155(13) 0.0111(14) 0.000 -0.0021(10) 0.000
C5 0.0127(9) 0.0136(9) 0.0139(10) 0.0019(7) 0.0024(7) 0.0011(7)
C6 0.0127(10) 0.0144(9) 0.0118(9) 0.0006(8) 0.0034(8) -0.0002(7)
N1 0.0117(11) 0.0135(11) 0.0081(11) 0.000 0.0018(9) 0.000
N2 0.0109(11) 0.0209(12) 0.0093(12) 0.000 0.0016(9) 0.000
N3 0.0118(8) 0.0155(8) 0.0110(8) 0.0006(7) -0.0028(6) -0.0013(6)
O1 0.0148(10) 0.0231(10) 0.0082(9) 0.000 0.0048(7) 0.000
O2 0.0187(11) 0.0496(13) 0.0083(11) 0.000 0.0066(8) 0.000
O3 0.0141(8) 0.0324(8) 0.0095(7) 0.0009(6) -0.0054(5) 0.0004(6)
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 121.0(2) . . ?
C2 C1 H1 119.5 . . ?
N1 C1 H1 119.5 . . ?
C1 C2 N2 120.6(2) . . ?
C1 C2 H2 119.7 . . ?
N2 C2 H2 119.7 . . ?
N2 C3 C4 120.6(3) . . ?
N2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
N1 C4 C3 120.8(2) . . ?
N1 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N3 C5 C6 120.94(17) . . ?
N3 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 N3 120.73(16) . 5_665 ?
C5 C6 H6 119.6 . . ?
N3 C6 H6 119.6 5_665 . ?
O1 N1 C4 120.3(2) . . ?
O1 N1 C1 121.3(2) . . ?
C4 N1 C1 118.4(2) . . ?
O2 N2 C3 120.3(2) . . ?
O2 N2 C2 121.2(2) . . ?
C3 N2 C2 118.6(2) . . ?
O3 N3 C5 120.88(16) . . ?
O3 N3 C6 120.79(15) . 5_665 ?
C5 N3 C6 118.32(15) . 5_665 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.356(4) . ?
C1 N1 1.359(3) . ?
C1 H1 0.9500 . ?
C2 N2 1.361(3) . ?
C2 H2 0.9500 . ?
C3 N2 1.358(3) . ?
C3 C4 1.361(4) . ?
C3 H3 0.9500 . ?
C4 N1 1.358(3) . ?
C4 H4 0.9500 . ?
C5 N3 1.357(2) . ?
C5 C6 1.358(3) . ?
C5 H5 0.9500 . ?
C6 N3 1.358(2) 5_665 ?
C6 H6 0.9500 . ?
N1 O1 1.301(3) . ?
N2 O2 1.293(3) . ?
N3 O3 1.2996(19) . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 0.000(1) . . . . ?
N2 C3 C4 N1 0.000(0) . . . . ?
N3 C5 C6 N3 1.4(3) . . . 5_665 ?
C3 C4 N1 O1 180.000(0) . . . . ?
C3 C4 N1 C1 0.000(0) . . . . ?
C2 C1 N1 O1 180.000(0) . . . . ?
C2 C1 N1 C4 0.000(0) . . . . ?
C4 C3 N2 O2 180.000(0) . . . . ?
C4 C3 N2 C2 0.000(0) . . . . ?
C1 C2 N2 O2 180.000(0) . . . . ?
C1 C2 N2 C3 0.000(0) . . . . ?
C6 C5 N3 O3 177.81(16) . . . . ?
C6 C5 N3 C6 -1.4(3) . . . 5_665 ?