#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/91/2209119.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2209119
loop_
_publ_author_name
'Beves, Jonathon E.'
'Constable, Edwin C.'
'Housecroft, Catherine E.'
'Neuburger, Markus'
'Schaffner, Silvia'
_publ_section_title
;
 4'-Chloro-2,2':6',2''-terpyridine
;
_journal_coeditor_code           CF2025
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2497
_journal_page_last               o2498
_journal_paper_doi               10.1107/S1600536806019180
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H10 Cl1 N3'
_chemical_formula_moiety         'C15 H10 Cl1 N3'
_chemical_formula_sum            'C15 H10 Cl N3'
_chemical_formula_weight         267.72
_chemical_name_systematic
;
4'-Chloro-2,2':6',2''-terpyridine
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           CRYSTALS_ver_12.82
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.8317(15)
_cell_length_b                   3.8344(2)
_cell_length_c                   10.6476(5)
_cell_measurement_reflns_used    3476
_cell_measurement_temperature    173
_cell_measurement_theta_max      27
_cell_measurement_theta_min      1
_cell_volume                     1217.94(11)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001)'
_computing_data_reduction        DENZO/SCALEPACK
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  CRYSTALS
_computing_structure_refinement  'CRYSTALS (Betteridge et al.,  2003)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.098
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7250
_diffrn_reflns_theta_full        25.341
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         1.37
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.18
_refine_ls_abs_structure_details 'Flack (1983), 1130 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.04(6)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9420
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1848
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0300
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
'w=1/[σ²(F²) + (0.02P)²] where P=[max(Fo²,0) + 2Fc²]/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0368
_refine_ls_wR_factor_gt          0.0320
_refine_ls_wR_factor_ref         0.0320
_reflns_number_gt                1848
_reflns_number_total             2554
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            cf2025.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_formula_sum        'C15 H10 Cl1 N3'
_cod_database_code               2209119
_cod_database_fobs_code          2209119
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,y+1/2,z+1/2
x+1/2,-y+1/2,z
-x,-y,z+1/2
loop_
_atom_site_type_symbol
_atom_site_label
_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
Cl Cl1 0.839243(18) 0.64167(15) 1.05641(7) 0.0391 Uani 1.0000
N N1 0.99400(6) 1.1265(5) 0.89573(16) 0.0304 Uani 1.0000
N N2 0.89799(5) 1.0349(4) 0.69348(16) 0.0276 Uani 1.0000
N N3 0.78951(6) 0.7575(5) 0.58118(17) 0.0350 Uani 1.0000
C C1 1.03672(8) 1.2342(7) 0.8905(2) 0.0345 Uani 1.0000
C C2 1.05556(8) 1.3886(6) 0.7862(2) 0.0342 Uani 1.0000
C C3 1.02932(8) 1.4367(6) 0.6809(2) 0.0332 Uani 1.0000
C C4 0.98525(7) 1.3210(6) 0.68374(19) 0.0304 Uani 1.0000
C C5 0.96894(7) 1.1684(5) 0.79145(19) 0.0263 Uani 1.0000
C C6 0.92195(7) 1.0365(5) 0.8001(2) 0.0262 Uani 1.0000
C C7 0.90514(7) 0.9187(6) 0.9141(2) 0.0281 Uani 1.0000
C C8 0.86177(7) 0.7951(6) 0.9158(2) 0.0298 Uani 1.0000
C C9 0.83628(7) 0.7896(6) 0.8088(2) 0.0299 Uani 1.0000
C C10 0.85575(7) 0.9135(5) 0.6982(2) 0.0275 Uani 1.0000
C C11 0.83026(6) 0.9081(5) 0.5776(2) 0.0277 Uani 1.0000
C C12 0.84819(7) 1.0452(6) 0.4684(2) 0.0319 Uani 1.0000
C C13 0.82400(8) 1.0238(6) 0.3580(2) 0.0366 Uani 1.0000
C C14 0.78250(8) 0.8660(6) 0.3603(2) 0.0375 Uani 1.0000
C C15 0.76683(8) 0.7425(7) 0.4730(2) 0.0386 Uani 1.0000
H H11 1.0552 1.2019 0.9634 0.0414 Uiso 1.0000
H H21 1.0864 1.4613 0.7868 0.0411 Uiso 1.0000
H H31 1.0413 1.5476 0.6073 0.0398 Uiso 1.0000
H H41 0.9663 1.3470 0.6114 0.0365 Uiso 1.0000
H H71 0.9231 0.9232 0.9890 0.0337 Uiso 1.0000
H H91 0.8061 0.7035 0.8098 0.0359 Uiso 1.0000
H H121 0.8771 1.1543 0.4693 0.0383 Uiso 1.0000
H H131 0.8359 1.1169 0.2812 0.0439 Uiso 1.0000
H H141 0.7650 0.8431 0.2850 0.0450 Uiso 1.0000
H H151 0.7376 0.6381 0.4743 0.0463 Uiso 1.0000
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 'International Tables Vol C 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_publ_flag
C1 N1 C5 117.12(18) ?
C6 N2 C10 118.00(18) ?
C11 N3 C15 116.8(2) ?
N1 C1 C2 123.6(2) no
N1 C1 H11 118.2 no
C2 C1 H11 118.2 no
C1 C2 C3 118.7(2) no
C1 C2 H21 120.6 no
C3 C2 H21 120.6 no
C2 C3 C4 118.5(2) no
C2 C3 H31 120.8 no
C4 C3 H31 120.8 no
C3 C4 C5 119.3(2) no
C3 C4 H41 120.4 no
C5 C4 H41 120.4 no
C4 C5 N1 122.76(18) no
C4 C5 C6 121.81(19) no
N1 C5 C6 115.43(18) no
C5 C6 N2 116.74(18) no
C5 C6 C7 120.18(19) no
N2 C6 C7 123.08(19) no
C6 C7 C8 117.5(2) no
C6 C7 H71 121.2 no
C8 C7 H71 121.2 no
Cl1 C8 C7 119.28(18) ?
Cl1 C8 C9 119.69(16) ?
C7 C8 C9 121.0(2) no
C8 C9 C10 117.7(2) no
C8 C9 H91 121.1 no
C10 C9 H91 121.1 no
C9 C10 N2 122.6(2) ?
C9 C10 C11 120.59(18) no
N2 C10 C11 116.74(19) no
C10 C11 N3 116.20(19) no
C10 C11 C12 121.39(18) no
N3 C11 C12 122.4(2) no
C11 C12 C13 119.4(2) no
C11 C12 H121 120.3 no
C13 C12 H121 120.3 no
C12 C13 C14 118.7(2) no
C12 C13 H131 120.7 no
C14 C13 H131 120.7 no
C13 C14 C15 118.2(2) no
C13 C14 H141 120.9 no
C15 C14 H141 120.9 no
C14 C15 N3 124.5(2) no
C14 C15 H151 117.8 no
N3 C15 H151 117.8 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C8 1.743(2) ?
N1 C1 1.341(3) ?
N1 C5 1.348(3) ?
N2 C6 1.341(3) ?
N2 C10 1.344(3) ?
N3 C11 1.346(3) ?
N3 C15 1.337(3) ?
C1 C2 1.378(3) no
C1 H11 0.960 no
C2 C3 1.380(3) no
C2 H21 0.960 no
C3 C4 1.388(3) no
C3 H31 0.960 no
C4 C5 1.376(3) no
C4 H41 0.960 no
C5 C6 1.493(3) ?
C6 C7 1.389(3) no
C7 C8 1.378(3) no
C7 H71 0.960 no
C8 C9 1.370(3) no
C9 C10 1.396(3) no
C9 H91 0.960 no
C10 C11 1.493(3) ?
C11 C12 1.384(3) no
C12 C13 1.382(3) no
C12 H121 0.960 no
C13 C14 1.378(3) no
C13 H131 0.960 no
C14 C15 1.373(3) no
C14 H141 0.960 no
C15 H151 0.960 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 581106
