#------------------------------------------------------------------------------
#$Date: 2017-05-03 04:44:26 +0300 (Wed, 03 May 2017) $
#$Revision: 195899 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/81/7228162.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_7228162
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         'C7 H3 Cl2 N'
_chemical_formula_sum            'C7 H3 Cl2 N'
_chemical_formula_weight         172.00
_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   geom
_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                 95.936(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8613(1)
_cell_length_b                   11.4201(2)
_cell_length_c                   16.0731(3)
_cell_measurement_reflns_used    3372
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      33.18
_cell_measurement_theta_min      3.11
_cell_volume                     704.97(3)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.999
_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  0.0192
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16341
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.387
_diffrn_reflns_theta_min         2.548
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  0.8520
_exptl_absorpt_correction_T_min  0.7072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       irregular
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         2526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0238
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0293P)²+0.2111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0650
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2264
_reflns_number_total             2526
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce00548b2.cif
_cod_data_source_block           Johu27fin
_cod_database_code               7228162
_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   0.707
_shelx_estimated_absorpt_t_max   0.852
_shelxl_version_number           2013-4
_shelx_res_file
;
TITL Johu27new in P2(1)/n
CELL 0.71073   3.8613  11.4201  16.0731  90.000  95.936  90.000
ZERR    4.00   0.0001   0.0002   0.0003   0.000   0.001   0.000
LATT 1
SYMM 0.5-X, 0.5+Y, 0.5-Z
SFAC C  H  N  Cl
UNIT 28  12  4  8
OMIT -3 64.8
L.S. 15
ACTA
BOND $H
FMAP 2
PLAN 5
SIZE 0.450 0.210 0.200
CONF
WPDB
HTAB
TEMP -120
WGHT    0.029300    0.211100
FVAR       0.24095
MOLE 1
CL1   4    0.217340    0.535737    0.904079    11.00000    0.03769    0.02390 =
         0.02254   -0.00360   -0.00576   -0.00045
CL2   4   -0.426567    0.473085    0.608954    11.00000    0.02966    0.02847 =
         0.02057    0.00138   -0.00387   -0.00021
N1    3   -0.093942    0.484124    0.757689    11.00000    0.02307    0.01957 =
         0.01890    0.00022    0.00027   -0.00009
C1    1    0.083577    0.438601    0.825020    11.00000    0.01992    0.01894 =
         0.01894   -0.00027    0.00160   -0.00187
C2    1    0.168212    0.319927    0.834862    11.00000    0.01932    0.02005 =
         0.02140    0.00287    0.00366    0.00009
C3    1    0.055000    0.246164    0.768203    11.00000    0.02875    0.01770 =
         0.02635    0.00099    0.00403   -0.00039
AFIX  43
H3    2    0.106791    0.164871    0.771517    11.00000   -1.20000
AFIX   0
C4    1   -0.132306    0.291226    0.697402    11.00000    0.02692    0.02003 =
         0.02316   -0.00265    0.00215   -0.00338
AFIX  43
H4    2   -0.213655    0.242449    0.651626    11.00000   -1.20000
AFIX   0
C5    1   -0.196053    0.410563    0.696171    11.00000    0.01963    0.02128 =
         0.01827    0.00080    0.00179   -0.00179
C6    1    0.361447    0.275154    0.908801    11.00000    0.02499    0.02323 =
         0.02594    0.00310    0.00399    0.00155
C7    1    0.523466    0.233400    0.968336    11.00000    0.03261    0.03103 =
         0.02932    0.00489   -0.00012    0.00569
AFIX 163
H7    2    0.653059    0.200002    1.015957    11.00000   -1.20000
AFIX   0
HKLF 4

REM  Johu27new in P2(1)/n
REM R1 =  0.0238 for    2264 Fo > 4sig(Fo)  and  0.0280 for all    2526 data
REM     91 parameters refined using      0 restraints

END

WGHT      0.0291      0.2111

REM No hydrogen bonds found for HTAB generation

REM Highest difference peak  0.398,  deepest hole -0.213,  1-sigma level  0.048
Q1    1   0.1241  0.2840  0.8028  11.00000  0.05    0.40
Q2    1   0.1241  0.3774  0.8360  11.00000  0.05    0.37
Q3    1  -0.1817  0.3511  0.6957  11.00000  0.05    0.35
Q4    1   0.0084  0.4575  0.7862  11.00000  0.05    0.35
Q5    1  -0.0518  0.2735  0.7354  11.00000  0.05    0.33
;
_shelx_res_checksum              277
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 0.21734(7) 0.53574(2) 0.90408(2) 0.02866(7) Uani 1 1 d . .
Cl2 Cl -0.42657(6) 0.47308(2) 0.60895(2) 0.02669(7) Uani 1 1 d . .
N1 N -0.0939(2) 0.48412(7) 0.75769(5) 0.02064(14) Uani 1 1 d . .
C1 C 0.0836(2) 0.43860(8) 0.82502(5) 0.01930(15) Uani 1 1 d . .
C2 C 0.1682(2) 0.31993(8) 0.83486(6) 0.02015(16) Uani 1 1 d . .
C3 C 0.0550(3) 0.24616(8) 0.76820(6) 0.02419(18) Uani 1 1 d . .
H3 H 0.1068 0.1649 0.7715 0.029 Uiso 1 1 calc R U
C4 C -0.1323(2) 0.29123(8) 0.69740(6) 0.02340(17) Uani 1 1 d . .
H4 H -0.2137 0.2424 0.6516 0.028 Uiso 1 1 calc R U
C5 C -0.1961(2) 0.41056(8) 0.69617(5) 0.01974(15) Uani 1 1 d . .
C6 C 0.3614(3) 0.27515(9) 0.90880(6) 0.02462(17) Uani 1 1 d . .
C7 C 0.5235(3) 0.23340(10) 0.96834(7) 0.0312(2) Uani 1 1 d . .
H7 H 0.6531 0.2000 1.0160 0.037 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
Cl1 0.03769(13) 0.02390(11) 0.02254(11) -0.00360(8) -0.00576(9) -0.00045(8)
Cl2 0.02966(12) 0.02847(12) 0.02057(11) 0.00138(8) -0.00387(8) -0.00021(8)
N1 0.0231(3) 0.0196(3) 0.0189(3) 0.0002(3) 0.0003(3) -0.0001(3)
C1 0.0199(3) 0.0189(4) 0.0189(4) -0.0003(3) 0.0016(3) -0.0019(3)
C2 0.0193(3) 0.0200(4) 0.0214(4) 0.0029(3) 0.0037(3) 0.0001(3)
C3 0.0288(4) 0.0177(4) 0.0264(4) 0.0010(3) 0.0040(3) -0.0004(3)
C4 0.0269(4) 0.0200(4) 0.0232(4) -0.0026(3) 0.0022(3) -0.0034(3)
C5 0.0196(3) 0.0213(4) 0.0183(3) 0.0008(3) 0.0018(3) -0.0018(3)
C6 0.0250(4) 0.0232(4) 0.0259(4) 0.0031(3) 0.0040(3) 0.0016(3)
C7 0.0326(5) 0.0310(5) 0.0293(5) 0.0049(4) -0.0001(4) 0.0057(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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C5 116.68(8)
N1 C1 C2 124.54(8)
N1 C1 Cl1 116.05(7)
C2 C1 Cl1 119.40(7)
C3 C2 C1 116.51(8)
C3 C2 C6 121.10(9)
C1 C2 C6 122.39(9)
C4 C3 C2 120.15(9)
C4 C3 H3 119.9
C2 C3 H3 119.9
C3 C4 C5 117.07(8)
C3 C4 H4 121.5
C5 C4 H4 121.5
N1 C5 C4 125.04(8)
N1 C5 Cl2 115.47(7)
C4 C5 Cl2 119.49(7)
C7 C6 C2 177.07(11)
C6 C7 H7 180.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7252(9)
Cl2 C5 1.7347(9)
N1 C1 1.3258(11)
N1 C5 1.3260(11)
C1 C2 1.3992(13)
C2 C3 1.3971(13)
C2 C6 1.4308(13)
C3 C4 1.3830(13)
C3 H3 0.9500
C4 C5 1.3847(13)
C4 H4 0.9500
C6 C7 1.1877(14)
C7 H7 0.9500
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
C5 N1 C1 C2 0.04(13)
C5 N1 C1 Cl1 179.50(7)
N1 C1 C2 C3 0.04(13)
Cl1 C1 C2 C3 -179.40(7)
N1 C1 C2 C6 179.83(9)
Cl1 C1 C2 C6 0.39(12)
C1 C2 C3 C4 -0.39(13)
C6 C2 C3 C4 179.82(9)
C2 C3 C4 C5 0.63(14)
C1 N1 C5 C4 0.23(13)
C1 N1 C5 Cl2 -179.84(6)
C3 C4 C5 N1 -0.57(14)
C3 C4 C5 Cl2 179.50(7)
