#------------------------------------------------------------------------------
#$Date: 2019-08-01 05:28:16 +0200 (jue 01 de ago de 2019) $
#$Revision: 217344 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/32/7233291.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_7233291
loop_
_publ_author_name
'Hloušková, Zuzana'
'Klikar, Milan'
'Pytela, Oldřich'
'Almonasy, Numan'
'R°užička, Aleš'
'Jandová, Veronika'
'Bureš, Filip'
_publ_section_title
;
 Structural elaboration of dicyanopyrazine: towards push--pull molecules
 with tailored photoredox activity
;
_journal_issue                   41
_journal_name_full               'RSC Advances'
_journal_page_first              23797
_journal_paper_doi               10.1039/C9RA04731J
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C8 H6 N4 O2'
_chemical_formula_sum            'C8 H6 N4 O2'
_chemical_formula_weight         190.17
_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'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'APEX3 v2016.5-0'
_audit_update_record
;
2019-02-16 deposited with the CCDC.    2019-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3323(7)
_cell_length_b                   14.8768(11)
_cell_length_c                   6.3126(5)
_cell_measurement_reflns_used    8519
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     876.41(12)
_computing_cell_refinement       'APEX3 v2016.5-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'Platon (Spek, 2009)'
_computing_publication_material  'Platon (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7842
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_min         3.506
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     65
_refine_ls_number_reflns         1043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0431
_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)+(0.0580P)²+0.1812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                826
_reflns_number_total             1043
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ra04731j2.cif
_cod_data_source_block           7
_cod_database_code               7233291
_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.
;
_exptl_absorpt_special_details
;
The ratio of minimum to maximum
apparent transmission was 0.879
;
_shelx_res_file
;

    mo_jty180108N1_0ma_a.res created by SHELXL-2014/7


TITL mo_jty180108N1_0ma_a.res in Pnma
REM Old TITL mo_jty180108N1_0ma in Pnma

REM SHELXT solution in Pnma
REM R1 0.104,  Rweak 0.003,  Alpha 0.025,  Orientation as input
REM Formula found by SHELXT:  C4 N2 O

CELL  0.71073   9.3323  14.8768   6.3126   90.000   90.000   90.000
ZERR   4.000   0.0007   0.0011   0.0005    0.000    0.000    0.000
LATT  1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, -Z
SYMM 1/2+X, 1/2-Y, 1/2-Z
SFAC C H N O
UNIT 32 24 16 8
ACTA
TEMP -123.170
L.S. 10
BOND $H
LIST 6
FMAP 2
PLAN 20
WGHT    0.058000    0.181200
FVAR       1.34311
O1    4    0.201398    0.338029    0.123848    11.00000    0.02934    0.01712 =
         0.02322    0.00285   -0.00700    0.00035
C1    1    0.395259    0.296138    0.588114    11.00000    0.01448    0.02298 =
         0.01834   -0.00182    0.00092   -0.00035
N1    3    0.332807    0.344555    0.431845    11.00000    0.01887    0.01862 =
         0.02101   -0.00025   -0.00015   -0.00081
N2    3    0.515838    0.382982    0.894945    11.00000    0.03472    0.04148 =
         0.03350   -0.01128   -0.00950   -0.00020
C2    1    0.269657    0.298569    0.282545    11.00000    0.01616    0.02002 =
         0.01879    0.00061    0.00092    0.00015
C3    1    0.462772    0.345154    0.757784    11.00000    0.02115    0.02625 =
         0.02412   -0.00073   -0.00147    0.00146
C4    1    0.195906    0.435699    0.129485    11.00000    0.03645    0.01664 =
         0.02705    0.00374   -0.00505    0.00150
AFIX 137
H4A   2    0.293607    0.459846    0.128895    11.00000   -1.50000
H4B   2    0.146365    0.455242    0.258387    11.00000   -1.50000
H4C   2    0.144044    0.457824    0.004969    11.00000   -1.50000
AFIX   0
HKLF 4

REM  mo_jty180108N1_0ma_a.res in Pnma
REM R1 =  0.0431 for     826 Fo > 4sig(Fo)  and  0.0606 for all    1043 data
REM     65 parameters refined using      0 restraints

END

WGHT      0.0581      0.1665

REM Highest difference peak  0.310,  deepest hole -0.235,  1-sigma level  0.045
Q1    1   0.2653  0.2500  0.2825  10.50000  0.05    0.31
Q2    1   0.4105  0.2500  0.5738  10.50000  0.05    0.24
Q3    1   0.5031  0.2500  0.9782  10.50000  0.05    0.16
Q4    1   0.1782  0.4380 -0.0421  11.00000  0.05    0.16
Q5    1   0.3846  0.4070  0.4514  11.00000  0.05    0.15
Q6    1   0.1205  0.2500  0.0414  10.50000  0.05    0.15
Q7    1   0.5093  0.3221  0.8809  11.00000  0.05    0.14
Q8    1   0.3054  0.3990  0.4537  11.00000  0.05    0.14
Q9    1   0.5751  0.4117  1.0024  11.00000  0.05    0.14
Q10   1   0.3318  0.3134  0.3202  11.00000  0.05    0.13
Q11   1   0.4597  0.3190  0.6370  11.00000  0.05    0.13
Q12   1   0.4858  0.3865  0.7625  11.00000  0.05    0.12
Q13   1   0.2620  0.3227  0.4000  11.00000  0.05    0.12
Q14   1   0.5419  0.3413  0.7458  11.00000  0.05    0.12
Q15   1   0.3396  0.3164  0.5419  11.00000  0.05    0.12
Q16   1   0.1991  0.2500 -0.1894  10.50000  0.05    0.12
Q17   1   0.3840  0.2500  0.9682  10.50000  0.05    0.12
Q18   1   0.4005  0.3138  0.4923  11.00000  0.05    0.11
Q19   1   0.1211  0.3209  0.0723  11.00000  0.05    0.11
Q20   1   0.4089  0.3123  0.6886  11.00000  0.05    0.11
;
_shelx_res_checksum              84855
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
O1 O 0.20140(11) 0.33803(6) 0.12385(15) 0.0232(3) Uani 1 1 d . .
C1 C 0.39526(14) 0.29614(9) 0.58811(19) 0.0186(3) Uani 1 1 d . .
N1 N 0.33281(12) 0.34456(7) 0.43185(18) 0.0195(3) Uani 1 1 d . .
N2 N 0.51584(15) 0.38298(10) 0.8949(2) 0.0366(4) Uani 1 1 d . .
C2 C 0.26966(14) 0.29857(9) 0.2825(2) 0.0183(3) Uani 1 1 d . .
C3 C 0.46277(16) 0.34515(10) 0.7578(2) 0.0238(3) Uani 1 1 d . .
C4 C 0.19591(17) 0.43570(9) 0.1295(2) 0.0267(4) Uani 1 1 d . .
H4A H 0.2936 0.4598 0.1289 0.040 Uiso 1 1 calc R U
H4B H 0.1464 0.4552 0.2584 0.040 Uiso 1 1 calc R U
H4C H 0.1440 0.4578 0.0050 0.040 Uiso 1 1 calc R U
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
O1 0.0293(6) 0.0171(5) 0.0232(5) 0.0029(4) -0.0070(4) 0.0003(4)
C1 0.0145(6) 0.0230(7) 0.0183(7) -0.0018(5) 0.0009(5) -0.0004(5)
N1 0.0189(6) 0.0186(6) 0.0210(6) -0.0002(4) -0.0002(5) -0.0008(5)
N2 0.0347(8) 0.0415(8) 0.0335(7) -0.0113(6) -0.0095(6) -0.0002(6)
C2 0.0162(7) 0.0200(7) 0.0188(7) 0.0006(5) 0.0009(5) 0.0002(5)
C3 0.0212(7) 0.0262(7) 0.0241(7) -0.0007(6) -0.0015(6) 0.0015(6)
C4 0.0364(8) 0.0166(7) 0.0270(7) 0.0037(6) -0.0051(6) 0.0015(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
C2 O1 C4 116.19(11) . .
N1 C1 C1 122.16(7) . 7_565
N1 C1 C3 117.44(12) . .
C1 C1 C3 120.41(8) 7_565 .
C2 N1 C1 116.22(11) . .
N1 C2 O1 122.08(12) . .
N1 C2 C2 121.61(8) . 7_565
O1 C2 C2 116.31(7) . 7_565
N2 C3 C1 178.85(16) . .
O1 C4 H4A 109.5 . .
O1 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
O1 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.3244(16) .
O1 C4 1.4544(16) .
C1 N1 1.3534(17) .
C1 C1 1.373(3) 7_565
C1 C3 1.4408(19) .
N1 C2 1.3052(17) .
N2 C3 1.1453(19) .
C2 C2 1.445(3) 7_565
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
