#------------------------------------------------------------------------------
#$Date: 2017-05-03 03:44:26 +0200 (Wed 03 de May de 2017) $
#$Revision: 195899 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/81/7228161.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_7228161
loop_
_publ_author_name
'Hübscher, Jörg'
'Seichter, Wilhelm'
'Weber, Edwin'
_publ_section_title
;
 Intermolecular contacts in the crystal structures of specifically varied
 halogen and protonic group substituted azines
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00548B
_journal_year                    2017
_chemical_formula_moiety         'C4 H3 Cl N2 O'
_chemical_formula_sum            'C4 H3 Cl N2 O'
_chemical_formula_weight         130.53
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-03-16 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.020(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.1254(1)
_cell_length_b                   10.6052(3)
_cell_length_c                   11.9696(3)
_cell_measurement_reflns_used    5462
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      2.57
_cell_volume                     520.79(2)
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_collection       'Kappa APEX 2 (Bruker-AXS)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 (Farrugia)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2015 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10674
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.098
_diffrn_reflns_theta_min         2.572
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  0.9191
_exptl_absorpt_correction_T_min  0.7617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_description       irregulat
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         1530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0268
_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)+(0.0426P)²+0.1473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0772
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1359
_reflns_number_total             1530
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce00548b2.cif
_cod_data_source_block           August1new
_cod_database_code               7228161
_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   0.762
_shelx_estimated_absorpt_t_max   0.919
_shelxl_version_number           2013-4
_shelx_res_file
;
TITL August_1_0m in P2(1)/n
CELL 0.71073   4.1254  10.6052  11.9696  90.000  96.020  90.000
ZERR    4.00   0.0001   0.0003   0.0003   0.000   0.002   0.000
LATT 1
SYMM 0.5-X, 0.5+Y, 0.5-Z
SFAC C  H  N  Cl O
UNIT 16  12  8  4  4
OMIT -3 60.2
L.S. 12
ACTA
BOND $H
FMAP 2
PLAN 5
HTAB N2 O1_$1
EQIV $1 -x+2, -y+1, -z+1
HTAB
SIZE 0.14 0.26 0.47
WPDB
CONF
TEMP -120
WGHT    0.042600    0.147300
FVAR       0.32909
MOLE 1
CL1   4    0.114109    0.407317    0.118799    11.00000    0.03419    0.03949 =
         0.02715   -0.00128   -0.00359    0.00603
O1    5    1.046590    0.334966    0.499258    11.00000    0.03801    0.02168 =
         0.02706   -0.00071   -0.00540   -0.00138
N2    3    0.702811    0.455318    0.384405    11.00000    0.02882    0.01857 =
         0.02525   -0.00166    0.00037   -0.00138
H2A   2    0.777159    0.524255    0.422904    11.00000    0.03947
N1    3    0.481898    0.477287    0.294406    11.00000    0.02661    0.02299 =
         0.02562    0.00077    0.00297    0.00081
C1    1    0.387607    0.379515    0.235589    11.00000    0.02537    0.02577 =
         0.02256   -0.00002    0.00390    0.00082
C2    1    0.494484    0.253795    0.259680    11.00000    0.03433    0.02228 =
         0.02430   -0.00334    0.00234   -0.00293
AFIX  43
H2    2    0.414780    0.185247    0.213622    11.00000   -1.20000
AFIX   0
C3    1    0.713556    0.235489    0.350496    11.00000    0.03700    0.01839 =
         0.02528   -0.00153    0.00126   -0.00083
AFIX  43
H3    2    0.787018    0.152714    0.370080    11.00000   -1.20000
AFIX   0
C4    1    0.835743    0.341697    0.417660    11.00000    0.02954    0.01912 =
         0.02293   -0.00040    0.00370   -0.00277
HKLF 4

REM  August_1_0m in P2(1)/n
REM R1 =  0.0268 for    1359 Fo > 4sig(Fo)  and  0.0316 for all    1530 data
REM     77 parameters refined using      0 restraints

END

WGHT      0.0412      0.1506

REM Instructions for potential hydrogen bonds
HTAB N2 O1_$1

REM Highest difference peak  0.356,  deepest hole -0.347,  1-sigma level  0.047
Q1    1   0.4477  0.3202  0.2441  11.00000  0.05    0.36
Q2    1   0.2483  0.4338  0.1007  11.00000  0.05    0.34
Q3    1   0.7844  0.2896  0.3801  11.00000  0.05    0.32
Q4    1   0.5552  0.2457  0.3190  11.00000  0.05    0.31
Q5    1   0.7630  0.3952  0.3987  11.00000  0.05    0.27
;
_shelx_res_checksum              21344
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Cl1 Cl 0.11411(7) 0.40732(3) 0.11880(2) 0.03409(11) Uani 1 1 d . .
O1 O 1.0466(2) 0.33497(8) 0.49926(7) 0.02954(19) Uani 1 1 d . .
N2 N 0.7028(2) 0.45532(9) 0.38441(8) 0.02439(19) Uani 1 1 d . .
H2A H 0.777(4) 0.5243(16) 0.4229(14) 0.039(4) Uiso 1 1 d . .
N1 N 0.4819(2) 0.47729(9) 0.29441(8) 0.0251(2) Uani 1 1 d . .
C1 C 0.3876(3) 0.37952(11) 0.23559(9) 0.0245(2) Uani 1 1 d . .
C2 C 0.4945(3) 0.25379(11) 0.25968(9) 0.0270(2) Uani 1 1 d . .
H2 H 0.4148 0.1852 0.2136 0.032 Uiso 1 1 calc R U
C3 C 0.7136(3) 0.23549(10) 0.35050(9) 0.0270(2) Uani 1 1 d . .
H3 H 0.7870 0.1527 0.3701 0.032 Uiso 1 1 calc R U
C4 C 0.8357(3) 0.34170(10) 0.41766(9) 0.0238(2) 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
Cl1 0.03419(17) 0.03949(19) 0.02715(16) -0.00128(11) -0.00359(11) 0.00603(11)
O1 0.0380(5) 0.0217(4) 0.0271(4) -0.0007(3) -0.0054(3) -0.0014(3)
N2 0.0288(5) 0.0186(4) 0.0252(4) -0.0017(3) 0.0004(4) -0.0014(3)
N1 0.0266(4) 0.0230(4) 0.0256(4) 0.0008(3) 0.0030(3) 0.0008(3)
C1 0.0254(5) 0.0258(5) 0.0226(5) 0.0000(4) 0.0039(4) 0.0008(4)
C2 0.0343(6) 0.0223(5) 0.0243(5) -0.0033(4) 0.0023(4) -0.0029(4)
C3 0.0370(6) 0.0184(5) 0.0253(5) -0.0015(4) 0.0013(4) -0.0008(4)
C4 0.0295(5) 0.0191(5) 0.0229(5) -0.0004(4) 0.0037(4) -0.0028(4)
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'
Cl Cl 0.1484 0.1585 '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
N1 N2 C4 126.79(10)
N1 N2 H2A 115.6(11)
C4 N2 H2A 117.5(11)
C1 N1 N2 115.75(10)
N1 C1 C2 124.93(10)
N1 C1 Cl1 116.00(9)
C2 C1 Cl1 119.06(9)
C3 C2 C1 117.62(10)
C3 C2 H2 121.2
C1 C2 H2 121.2
C2 C3 C4 120.02(10)
C2 C3 H3 120.0
C4 C3 H3 120.0
O1 C4 N2 120.49(10)
O1 C4 C3 124.67(10)
N2 C4 C3 114.83(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7272(11)
O1 C4 1.2399(14)
N2 N1 1.3562(13)
N2 C4 1.3658(14)
N2 H2A 0.901(17)
N1 C1 1.2902(15)
C1 C2 1.4243(16)
C2 C3 1.3528(16)
C2 H2 0.9500
C3 C4 1.4436(15)
C3 H3 0.9500
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 H2A O1 0.901(17) 1.866(17) 2.7663(12) 177.0(16) 3_766
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 N2 N1 C1 0.73(16)
N2 N1 C1 C2 0.95(16)
N2 N1 C1 Cl1 -178.42(7)
N1 C1 C2 C3 -0.61(18)
Cl1 C1 C2 C3 178.74(9)
C1 C2 C3 C4 -1.30(17)
N1 N2 C4 O1 176.97(10)
N1 N2 C4 C3 -2.47(16)
C2 C3 C4 O1 -176.75(11)
C2 C3 C4 N2 2.66(16)
