#------------------------------------------------------------------------------
#$Date: 2016-03-26 23:00:42 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180526 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/95/7219517.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_7219517
loop_
_publ_author_name
'Long, Sihui'
'Zhou, Panpan'
'Parkin, Sean'
'Li, Tonglei'
_publ_section_title
;
 Polymorphism and solid-to-solid phase transitions of a simple organic
 molecule, 3-chloroisonicotinic acid
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              2389
_journal_paper_doi               10.1039/C4CE02563F
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C6 H4 Cl N O2'
_chemical_formula_sum            'C6 H4 Cl N O2'
_chemical_formula_weight         157.55
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-2014/7 and CIFFIX'
_audit_update_record
;
2015-02-02 deposited with the CCDC.
2015-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                61.6975(14)
_cell_angle_beta                 80.0002(12)
_cell_angle_gamma                89.5122(12)
_cell_formula_units_Z            1
_cell_length_a                   3.6779(1)
_cell_length_b                   6.9371(1)
_cell_length_c                   7.0372(2)
_cell_measurement_reflns_used    667
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     155.117(7)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 2006)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 2006)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 9.1
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans at fixed χ = 55°'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_number            1334
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         5.882
_diffrn_source                   'fine-focus sealed-tube'
_exptl_absorpt_coefficient_mu    0.538
_exptl_absorpt_correction_T_max  0.9482
_exptl_absorpt_correction_T_min  0.8137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_description       block
_exptl_crystal_F_000             80
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
; 
Flack 'x' determined using 651 quotients [(I+)-(I-)]/[(I+)+(I-)] 
[Parsons, Flack and Wagner (2013)]. 
;
_refine_ls_abs_structure_Flack   0.010(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1334
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0165
_refine_ls_R_factor_gt           0.0164
_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)+(0.0200P)²+0.0220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0461
_refine_ls_wR_factor_ref         0.0461
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_full    0.937
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                1332
_reflns_number_total             1334
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
; 
 
    k08179r.res created by SHELXL-2014/7 
 
 
TITL k08179 
CELL 0.71073   3.6779   6.9371   7.0372  61.6975  80.0002  89.5122 
ZERR       1   0.0001   0.0001   0.0002   0.0014   0.0012   0.0012 
LATT -1 
SFAC C  H  Cl N  O 
UNIT     6    4    1    1    2 
SIZE 0.40 0.20 0.10 
TEMP -183 
REM FORM block 
REM COLR colourless 
CONF 
BOND $H 
REM Instructions for potential hydrogen bonds 
EQIV $1 x, y, z+1 
HTAB C5 Cl1_$1 
EQIV $2 x-1, y-1, z+1 
HTAB O2 N1_$2 
WPDB 
ACTA 
LIST 4 
ACTA 
BOND $H 
FMAP 2 
PLAN 5 
L.S.  8 
OMIT  -2.0000 55 
WGHT    0.020000    0.022000 
FVAR       7.29346 
CL1   3    0.434008    0.164974    0.290025    11.00000    0.01745    0.01204 = 
         0.01096   -0.00701   -0.00236   -0.00127 
N1    4    0.835451    0.692143    0.282350    11.00000    0.01416    0.00923 = 
         0.01008   -0.00263    0.00028   -0.00052 
C2    1    0.736324    0.543386    0.227896    11.00000    0.01200    0.01176 = 
         0.00855   -0.00369   -0.00047    0.00097 
AFIX  43 
H2A   2    0.782593    0.579343    0.077239    11.00000   -1.20000 
AFIX   0 
C3    1    0.566189    0.335877    0.385851    11.00000    0.00977    0.00786 = 
         0.01004   -0.00440   -0.00111   -0.00034 
C4    1    0.498703    0.280493    0.606709    11.00000    0.00855    0.00780 = 
         0.00916   -0.00166   -0.00021   -0.00019 
C5    1    0.597147    0.440771    0.659867    11.00000    0.01519    0.01065 = 
         0.00791   -0.00376   -0.00153    0.00033 
AFIX  43 
H5    2    0.548260    0.411316    0.808635    11.00000   -1.20000 
AFIX   0 
C6    1    0.766060    0.642460    0.494924    11.00000    0.01353    0.00940 = 
         0.01147   -0.00488   -0.00078   -0.00084 
AFIX  43 
H6    2    0.835105    0.749155    0.533375    11.00000   -1.20000 
AFIX   0 
C7    1    0.333358    0.056786    0.789303    11.00000    0.01389    0.00896 = 
         0.00676   -0.00219   -0.00181   -0.00167 
O1    5    0.402805   -0.112185    0.784869    11.00000    0.02870    0.00931 = 
         0.01404   -0.00501    0.00091    0.00051 
O2    5    0.119200    0.071519    0.951432    11.00000    0.01850    0.00780 = 
         0.00764   -0.00144    0.00362   -0.00425 
AFIX 147 
H2    2    0.043228   -0.055160    1.054444    11.00000   -1.50000 
 
AFIX   0 
HKLF 4 
 
REM  k08179 
REM R1 =  0.0164 for    1332 Fo > 4sig(Fo)  and  0.0165 for all    1334 data 
REM     92 parameters refined using      3 restraints 
 
END 
 
WGHT      0.0189      0.0231 
 
REM Highest difference peak  0.215,  deepest hole -0.176,  1-sigma level  0.034 
Q1    1   0.4095  0.1623  0.6945  11.00000  0.05    0.21 
Q2    1   0.6591  0.4415  0.3007  11.00000  0.05    0.18 
Q3    1  -0.0348 -0.1732  1.1869  11.00000  0.05    0.16 
Q4    1   0.5028  0.3774  0.6200  11.00000  0.05    0.14 
Q5    1   0.6822  0.1613  0.2532  11.00000  0.05    0.14 
;
_cod_data_source_file            c4ce02563f2.cif
_cod_data_source_block           III
_cod_depositor_comments
'Adding full bibliography for 7219515--7219517.cif.'
_cod_database_code               7219517
#BEGIN Tags that were not found in dictionaries:
_shelx_shelxl_version_number     2014/7
_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   0.814
_shelx_estimated_absorpt_t_max   0.948
_exptl_absorpt_special_details
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal longer than 
the x-ray beam cross section, absorption by the crystal mounting fibre etc. 
These account, by and large, for much of the difference between estimated 
values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;
_shelx_res_checksum              7351
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
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 0.43401(4) 0.16497(3) 0.29003(3) 0.01290(13) Uani 1 1 d . .
N1 N 0.8355(4) 0.6921(2) 0.2824(3) 0.0123(3) Uani 1 1 d . .
C2 C 0.7363(5) 0.5434(3) 0.2279(3) 0.0115(3) Uani 1 1 d . .
H2A H 0.7826 0.5793 0.0772 0.014 Uiso 1 1 calc R U
C3 C 0.5662(5) 0.3359(3) 0.3859(3) 0.0093(3) Uani 1 1 d . .
C4 C 0.4987(5) 0.2805(3) 0.6067(3) 0.0097(3) Uani 1 1 d . .
C5 C 0.5971(5) 0.4408(3) 0.6599(3) 0.0116(4) Uani 1 1 d . .
H5 H 0.5483 0.4113 0.8086 0.014 Uiso 1 1 calc R U
C6 C 0.7661(5) 0.6425(3) 0.4949(3) 0.0117(3) Uani 1 1 d . .
H6 H 0.8351 0.7492 0.5334 0.014 Uiso 1 1 calc R U
C7 C 0.3334(5) 0.0568(3) 0.7893(3) 0.0105(3) Uani 1 1 d . .
O1 O 0.4028(4) -0.1122(2) 0.7849(2) 0.0183(3) Uani 1 1 d . .
O2 O 0.1192(4) 0.0715(2) 0.9514(2) 0.0131(3) Uani 1 1 d . .
H2 H 0.0432 -0.0552 1.0544 0.020 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 0.0174(2) 0.01204(19) 0.01096(18) -0.00701(13) -0.00236(12) -0.00127(12)
N1 0.0142(7) 0.0092(7) 0.0101(7) -0.0026(6) 0.0003(6) -0.0005(5)
C2 0.0120(8) 0.0118(8) 0.0085(8) -0.0037(6) -0.0005(6) 0.0010(6)
C3 0.0098(7) 0.0079(8) 0.0100(7) -0.0044(6) -0.0011(6) -0.0003(6)
C4 0.0085(7) 0.0078(7) 0.0092(8) -0.0017(6) -0.0002(6) -0.0002(6)
C5 0.0152(8) 0.0106(8) 0.0079(8) -0.0038(7) -0.0015(6) 0.0003(6)
C6 0.0135(7) 0.0094(8) 0.0115(8) -0.0049(6) -0.0008(6) -0.0008(6)
C7 0.0139(8) 0.0090(8) 0.0068(7) -0.0022(6) -0.0018(6) -0.0017(6)
O1 0.0287(7) 0.0093(6) 0.0140(7) -0.0050(5) 0.0009(6) 0.0005(5)
O2 0.0185(6) 0.0078(6) 0.0076(6) -0.0014(5) 0.0036(5) -0.0042(5)
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'
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
C2 N1 C6 119.05(15)
N1 C2 C3 121.98(17)
N1 C2 H2A 119.0
C3 C2 H2A 119.0
C4 C3 C2 119.68(16)
C4 C3 Cl1 123.46(13)
C2 C3 Cl1 116.80(14)
C3 C4 C5 117.41(15)
C3 C4 C7 123.33(15)
C5 C4 C7 119.24(15)
C6 C5 C4 119.75(16)
C6 C5 H5 120.1
C4 C5 H5 120.1
N1 C6 C5 122.10(16)
N1 C6 H6 118.9
C5 C6 H6 118.9
O1 C7 O2 125.69(16)
O1 C7 C4 122.95(16)
O2 C7 C4 111.33(14)
C7 O2 H2 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.7258(18)
N1 C2 1.332(2)
N1 C6 1.342(2)
C2 C3 1.398(2)
C2 H2A 0.9500
C3 C4 1.388(2)
C4 C5 1.398(3)
C4 C7 1.511(2)
C5 C6 1.384(2)
C5 H5 0.9500
C6 H6 0.9500
C7 O1 1.211(2)
C7 O2 1.315(2)
O2 H2 0.8400
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
C5 H5 Cl1 0.95 2.93 3.8387(17) 159.9 1_556
O2 H2 N1 0.84 1.78 2.613(2) 172.9 1_446
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
C6 N1 C2 C3 -0.8(3)
N1 C2 C3 C4 -0.4(2)
N1 C2 C3 Cl1 177.10(13)
C2 C3 C4 C5 1.8(2)
Cl1 C3 C4 C5 -175.50(14)
C2 C3 C4 C7 -176.97(16)
Cl1 C3 C4 C7 5.7(2)
C3 C4 C5 C6 -2.1(2)
C7 C4 C5 C6 176.73(15)
C2 N1 C6 C5 0.5(3)
C4 C5 C6 N1 1.0(3)
C3 C4 C7 O1 36.3(3)
C5 C4 C7 O1 -142.46(18)
C3 C4 C7 O2 -145.64(16)
C5 C4 C7 O2 35.6(2)
