#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/19/1511939.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_1511939
loop_
_publ_author_name
'Scales, Stephanie'
'Johnson, Sarah'
'Hu, Qiyue'
'Do, Quyen-Quyen'
'Richardson, Paul'
'Wang, Fen'
'Braganza, John'
'Ren, Shijian'
'Wan, Yadong'
'Zheng, Baojiang'
'Faizi, Darius'
'McAlpine, Indrawan'
_publ_section_title
;
 Studies on the Regioselective Nucleophilic Aromatic Substitution (SNAr)
 Reaction of 2-Substituted 3,5-Dichloropyrazines
;
_journal_issue                   9
_journal_name_full               'Organic Letters'
_journal_page_first              2156
_journal_paper_doi               10.1021/ol4006695
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C5 H Cl2 N3'
_chemical_formula_sum            'C5 H Cl2 N3'
_chemical_formula_weight         173.99
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 108.605(3)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   10.9565(10)
_cell_length_b                   5.7167(6)
_cell_length_c                   16.5950(15)
_cell_measurement_reflns_used    2219
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      3.75
_cell_volume                     985.11(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6211
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.350
_diffrn_reflns_theta_min         2.590
_diffrn_source                   'micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.897
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_density_meas      ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2007
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[σ²(Fo²)+(0.0345P)²+0.5977P] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0875
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1556
_reflns_number_total             2007
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol4006695_si_001.cif
_cod_data_source_block           dichloropyrazine_carbonitrile
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               1511939
#BEGIN Tags that were not found in dictionaries:
_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   0.877
_shelx_estimated_absorpt_t_max   0.974
#END Tags that were not found in dictionaries
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.99887(6) 0.33385(11) 1.24216(3) 0.02783(18) Uani 1 1 d . . . . .
Cl2 Cl 0.64844(6) 0.15599(14) 0.95449(3) 0.0381(2) Uani 1 1 d . . . . .
N1 N 0.82297(17) 0.2156(3) 1.10124(11) 0.0194(4) Uani 1 1 d . . . . .
N2 N 0.76016(17) -0.2009(4) 1.16814(11) 0.0208(4) Uani 1 1 d . . . . .
N3 N 0.96390(19) -0.1618(4) 1.37329(12) 0.0259(5) Uani 1 1 d . . . . .
C1 C 0.8811(2) 0.1514(4) 1.18088(13) 0.0177(5) Uani 1 1 d . . . . .
C2 C 0.8499(2) -0.0532(4) 1.21515(13) 0.0172(5) Uani 1 1 d . . . . .
C3 C 0.9131(2) -0.1149(4) 1.30340(14) 0.0195(5) Uani 1 1 d . . . . .
C4 C 0.7323(2) 0.0708(5) 1.05659(13) 0.0218(5) Uani 1 1 d . . . . .
C5 C 0.7014(2) -0.1387(4) 1.08791(14) 0.0220(5) Uani 1 1 d . . . . .
H5 H 0.6378 -0.2382 1.0517 0.026 Uiso 1 1 calc R U . . .
Cl1' Cl 0.77840(12) 0.6763(2) 0.90367(7) 0.0262(3) Uani 0.5 1 d . . P A -1
Cl2' Cl 1.1560(2) 0.7851(4) 1.18509(18) 0.0259(5) Uani 0.5 1 d . . P A -1
N1' N 0.9746(7) 0.7042(10) 1.0425(4) 0.0185(11) Uani 0.5 1 d . . P A -1
N2' N 1.0829(5) 0.2852(11) 1.0122(4) 0.0251(11) Uani 0.5 1 d . . P A -1
N3' N 0.8693(10) 0.1346(14) 0.8195(7) 0.037(2) Uani 0.5 1 d . . P A -1
C1' C 0.9197(5) 0.5780(12) 0.9735(4) 0.0170(10) Uani 0.5 1 d . . P A -1
C2' C 0.9728(8) 0.3694(11) 0.9573(5) 0.0198(13) Uani 0.5 1 d . . P A -1
C3' C 0.9148(5) 0.2358(12) 0.8804(4) 0.0222(11) Uani 0.5 1 d . . P A -1
C4' C 1.0824(6) 0.6220(11) 1.0957(5) 0.0212(12) Uani 0.5 1 d . . P A -1
C5' C 1.1376(5) 0.4111(9) 1.0812(4) 0.0231(11) Uani 0.5 1 d . . P A -1
H5' H 1.2154 0.3580 1.1215 0.028 Uiso 0.5 1 calc R U P A -1
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 0.0344(3) 0.0218(3) 0.0236(3) -0.0022(2) 0.0041(3) -0.0111(3)
Cl2 0.0312(3) 0.0650(5) 0.0164(3) 0.0065(3) 0.0052(2) -0.0161(3)
N1 0.0200(10) 0.0223(11) 0.0181(9) -0.0020(8) 0.0094(8) 0.0005(8)
N2 0.0205(10) 0.0224(12) 0.0225(10) -0.0039(8) 0.0110(8) -0.0039(8)
N3 0.0251(11) 0.0249(12) 0.0272(11) 0.0033(9) 0.0076(9) 0.0010(9)
C1 0.0175(11) 0.0166(12) 0.0212(11) -0.0050(9) 0.0092(9) 0.0017(9)
C2 0.0154(11) 0.0181(13) 0.0205(11) -0.0020(9) 0.0091(9) 0.0017(9)
C3 0.0176(11) 0.0151(13) 0.0272(13) -0.0020(10) 0.0091(10) -0.0003(9)
C4 0.0195(11) 0.0319(15) 0.0173(10) -0.0032(10) 0.0103(9) -0.0012(10)
C5 0.0195(11) 0.0289(15) 0.0209(11) -0.0065(10) 0.0111(9) -0.0066(10)
Cl1' 0.0272(7) 0.0227(7) 0.0265(6) 0.0014(5) 0.0054(5) 0.0074(6)
Cl2' 0.0237(9) 0.0314(13) 0.0242(8) -0.0021(10) 0.0099(7) -0.0075(9)
N1' 0.025(3) 0.018(3) 0.020(3) 0.003(2) 0.017(3) -0.002(2)
N2' 0.029(3) 0.022(3) 0.030(3) 0.003(3) 0.017(3) 0.003(2)
N3' 0.049(5) 0.029(5) 0.039(4) -0.005(4) 0.023(4) 0.004(3)
C1' 0.018(3) 0.016(3) 0.019(3) 0.006(3) 0.010(3) 0.001(2)
C2' 0.021(3) 0.017(3) 0.028(4) -0.001(3) 0.018(3) 0.001(3)
C3' 0.026(3) 0.017(3) 0.029(3) 0.000(3) 0.017(3) 0.000(2)
C4' 0.021(3) 0.029(4) 0.016(3) 0.002(3) 0.008(2) -0.008(2)
C5' 0.016(3) 0.021(3) 0.032(3) 0.011(2) 0.007(2) 0.007(2)
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C4 115.0(2)
C5 N2 C2 116.4(2)
N1 C1 C2 122.6(2)
N1 C1 Cl1 117.03(18)
C2 C1 Cl1 120.33(16)
N2 C2 C1 121.47(19)
N2 C2 C3 117.4(2)
C1 C2 C3 121.2(2)
N3 C3 C2 179.3(3)
N1 C4 C5 124.0(2)
N1 C4 Cl2 116.37(19)
C5 C4 Cl2 119.67(18)
N2 C5 C4 120.5(2)
N2 C5 H5 119.8
C4 C5 H5 119.8
C4' N1' C1' 116.7(7)
C5' N2' C2' 116.8(6)
N1' C1' C2' 122.1(6)
N1' C1' Cl1' 118.1(6)
C2' C1' Cl1' 119.8(7)
N2' C2' C1' 121.1(6)
N2' C2' C3' 117.0(7)
C1' C2' C3' 121.9(9)
N3' C3' C2' 178.9(8)
N1' C4' C5' 122.4(8)
N1' C4' Cl2' 117.3(5)
C5' C4' Cl2' 120.3(6)
N2' C5' C4' 121.0(7)
N2' C5' H5' 119.5
C4' C5' H5' 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.718(2)
Cl2 C4 1.720(2)
N1 C1 1.323(3)
N1 C4 1.323(3)
N2 C5 1.329(3)
N2 C2 1.341(3)
N3 C3 1.147(3)
C1 C2 1.390(3)
C2 C3 1.450(3)
C4 C5 1.390(3)
C5 H5 0.9500
Cl1' C1' 1.705(6)
Cl2' C4' 1.720(9)
N1' C4' 1.315(8)
N1' C1' 1.325(9)
N2' C5' 1.322(8)
N2' C2' 1.347(10)
N3' C3' 1.132(11)
C1' C2' 1.390(8)
C2' C3' 1.450(9)
C4' C5' 1.404(8)
C5' H5' 0.9500
