#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/47/7004748.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_7004748
loop_
_publ_author_name
'Constable, Edwin C.'
'Figgemeier, Egbert'
'Housecroft, Catherine E.'
'Kokatam, Swarna Latha'
'Medlycott, Elaine A.'
'Neuburger, Markus'
'Schaffner, Silvia'
'Zampese, Jennifer A.'
_publ_section_title
;
 Wiring terpyridine: approaches to alkynylthienyl
 2,2′:6′,2″-terpyridines
;
_journal_issue                   47
_journal_name_full               'Dalton Transactions'
_journal_page_first              6752
_journal_page_last               6762
_journal_paper_doi               10.1039/b811747k
_journal_year                    2008
_chemical_formula_moiety         'C19 H12 Br N3 S'
_chemical_formula_sum            'C19 H12 Br N3 S'
_chemical_formula_weight         394.29
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_creation_date             06-12-18
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                90
_cell_angle_beta                 97.1365(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.05460(10)
_cell_length_b                   8.78370(10)
_cell_length_c                   18.2893(2)
_cell_measurement_reflns_used    7055
_cell_measurement_temperature    173
_cell_measurement_theta_max      28
_cell_measurement_theta_min      1
_cell_volume                     1602.74(3)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13984
_diffrn_reflns_theta_full        27.882
_diffrn_reflns_theta_max         27.882
_diffrn_reflns_theta_min         2.204
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.700
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0852
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2947
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0217
_refine_ls_shift/su_max          0.000710
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
0.325 0.132 0.130
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0313
_refine_ls_wR_factor_gt          0.0239
_refine_ls_wR_factor_ref         0.0239
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                2947
_reflns_number_total             3823
_reflns_threshold_expression     I>3.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          0.3830(4)
_oxford_structure_analysis_title '12181351 em2_173k'
_cod_data_source_file            b811747k.txt
_cod_data_source_block           em2_173k
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_original_formula_sum        'C19 H12 Br1 N3 S1'
_cod_database_code               7004748
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Br1 Br 0.221684(17) 0.586211(19) 0.434744(10) 0.0359 1.0000 Uani . . . . . .
S1 S 0.38990(4) 0.15188(5) 0.51635(2) 0.0331 1.0000 Uani . . . . . .
N1 N -0.21969(13) 0.09336(16) 0.63925(8) 0.0309 1.0000 Uani . . . . . .
N2 N 0.03836(13) -0.19176(15) 0.64167(7) 0.0273 1.0000 Uani . . . . . .
N3 N 0.35940(14) -0.36919(17) 0.64026(8) 0.0356 1.0000 Uani . . . . . .
C1 C -0.34305(16) 0.1072(2) 0.65874(10) 0.0345 1.0000 Uani . . . . . .
C2 C -0.41051(17) -0.0084(2) 0.68925(10) 0.0369 1.0000 Uani . . . . . .
C3 C -0.34663(18) -0.1467(2) 0.70238(10) 0.0396 1.0000 Uani . . . . . .
C4 C -0.21919(17) -0.1644(2) 0.68230(10) 0.0345 1.0000 Uani . . . . . .
C5 C -0.15924(15) -0.04239(18) 0.65053(8) 0.0275 1.0000 Uani . . . . . .
C6 C -0.02309(15) -0.05707(18) 0.62702(8) 0.0270 1.0000 Uani . . . . . .
C7 C 0.03519(16) 0.06161(18) 0.59249(9) 0.0288 1.0000 Uani . . . . . .
C8 C 0.16258(15) 0.04240(18) 0.57102(8) 0.0270 1.0000 Uani . . . . . .
C9 C 0.22700(15) -0.09726(19) 0.58695(9) 0.0290 1.0000 Uani . . . . . .
C10 C 0.16196(15) -0.20943(18) 0.62271(8) 0.0274 1.0000 Uani . . . . . .
C11 C 0.22711(16) -0.35840(18) 0.64418(8) 0.0283 1.0000 Uani . . . . . .
C12 C 0.15256(17) -0.47697(19) 0.66909(9) 0.0331 1.0000 Uani . . . . . .
C13 C 0.21680(19) -0.6105(2) 0.69248(10) 0.0374 1.0000 Uani . . . . . .
C14 C 0.35309(19) -0.6228(2) 0.68968(9) 0.0367 1.0000 Uani . . . . . .
C15 C 0.41874(18) -0.5010(2) 0.66297(10) 0.0397 1.0000 Uani . . . . . .
C16 C 0.22515(15) 0.16524(18) 0.53323(8) 0.0271 1.0000 Uani . . . . . .
C17 C 0.17096(15) 0.30214(18) 0.50822(9) 0.0284 1.0000 Uani . . . . . .
C18 C 0.26400(16) 0.39261(18) 0.47636(9) 0.0282 1.0000 Uani . . . . . .
C19 C 0.38682(16) 0.32811(19) 0.47650(9) 0.0328 1.0000 Uani . . . . . .
H11 H -0.3837 0.2069 0.6499 0.0425 1.0000 Uiso R . . . . .
H21 H -0.4989 0.0073 0.7026 0.0446 1.0000 Uiso R . . . . .
H31 H -0.3884 -0.2293 0.7251 0.0492 1.0000 Uiso R . . . . .
H41 H -0.1728 -0.2605 0.6887 0.0421 1.0000 Uiso R . . . . .
H71 H -0.0126 0.1551 0.5841 0.0352 1.0000 Uiso R . . . . .
H91 H 0.3159 -0.1166 0.5728 0.0342 1.0000 Uiso R . . . . .
H121 H 0.0570 -0.4661 0.6711 0.0405 1.0000 Uiso R . . . . .
H131 H 0.1687 -0.6973 0.7116 0.0456 1.0000 Uiso R . . . . .
H141 H 0.4006 -0.7141 0.7071 0.0447 1.0000 Uiso R . . . . .
H151 H 0.5139 -0.5108 0.6592 0.0485 1.0000 Uiso R . . . . .
H171 H 0.0812 0.3340 0.5116 0.0348 1.0000 Uiso R . . . . .
H191 H 0.4623 0.3696 0.4562 0.0408 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C16 . S1 . C19 . 92.74(8) yes
C1 . N1 . C5 . 117.17(14) yes
C6 . N2 . C10 . 117.89(14) yes
C11 . N3 . C15 . 116.64(15) yes
N1 . C1 . C2 . 124.11(16) yes
N1 . C1 . H11 . 115.0 no
C2 . C1 . H11 . 120.9 no
C1 . C2 . C3 . 118.48(15) yes
C1 . C2 . H21 . 121.0 no
C3 . C2 . H21 . 120.5 no
C2 . C3 . C4 . 118.59(17) yes
C2 . C3 . H31 . 121.4 no
C4 . C3 . H31 . 120.0 no
C3 . C4 . C5 . 119.15(16) yes
C3 . C4 . H41 . 121.1 no
C5 . C4 . H41 . 119.7 no
C4 . C5 . N1 . 122.47(15) yes
C4 . C5 . C6 . 120.98(14) yes
N1 . C5 . C6 . 116.55(14) yes
C5 . C6 . N2 . 115.71(14) yes
C5 . C6 . C7 . 121.46(14) yes
N2 . C6 . C7 . 122.83(14) yes
C6 . C7 . C8 . 119.47(14) yes
C6 . C7 . H71 . 119.2 no
C8 . C7 . H71 . 121.4 no
C7 . C8 . C9 . 117.66(14) yes
C7 . C8 . C16 . 120.43(14) yes
C9 . C8 . C16 . 121.91(14) yes
C8 . C9 . C10 . 119.09(14) yes
C8 . C9 . H91 . 120.8 no
C10 . C9 . H91 . 120.1 no
C9 . C10 . N2 . 123.04(14) yes
C9 . C10 . C11 . 121.86(14) yes
N2 . C10 . C11 . 115.08(14) yes
C10 . C11 . N3 . 116.89(15) yes
C10 . C11 . C12 . 120.32(14) yes
N3 . C11 . C12 . 122.76(15) yes
C11 . C12 . C13 . 119.11(16) yes
C11 . C12 . H121 . 120.9 no
C13 . C12 . H121 . 119.9 no
C12 . C13 . C14 . 118.87(17) yes
C12 . C13 . H131 . 122.2 no
C14 . C13 . H131 . 118.9 no
C13 . C14 . C15 . 118.25(16) yes
C13 . C14 . H141 . 120.3 no
C15 . C14 . H141 . 121.4 no
C14 . C15 . N3 . 124.35(16) yes
C14 . C15 . H151 . 118.4 no
N3 . C15 . H151 . 117.3 no
C8 . C16 . S1 . 120.81(11) yes
C8 . C16 . C17 . 128.72(14) yes
S1 . C16 . C17 . 110.45(12) yes
C16 . C17 . C18 . 112.04(14) yes
C16 . C17 . H171 . 125.0 no
C18 . C17 . H171 . 122.9 no
Br1 . C18 . C17 . 123.14(11) yes
Br1 . C18 . C19 . 122.36(12) yes
C17 . C18 . C19 . 114.49(14) yes
S1 . C19 . C18 . 110.29(12) yes
S1 . C19 . H191 . 122.5 no
C18 . C19 . H191 . 127.2 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . C18 . 1.8899(15) yes
S1 . C16 . 1.7264(15) yes
S1 . C19 . 1.7096(17) yes
N1 . C1 . 1.338(2) yes
N1 . C5 . 1.343(2) yes
N2 . C6 . 1.346(2) yes
N2 . C10 . 1.3401(19) yes
N3 . C11 . 1.344(2) yes
N3 . C15 . 1.344(2) yes
C1 . C2 . 1.377(3) yes
C1 . H11 . 0.972 no
C2 . C3 . 1.381(3) yes
C2 . H21 . 0.960 no
C3 . C4 . 1.385(2) yes
C3 . H31 . 0.959 no
C4 . C5 . 1.392(2) yes
C4 . H41 . 0.964 no
C5 . C6 . 1.491(2) yes
C6 . C7 . 1.386(2) yes
C7 . C8 . 1.396(2) yes
C7 . H71 . 0.954 no
C8 . C9 . 1.401(2) yes
C8 . C16 . 1.465(2) yes
C9 . C10 . 1.390(2) yes
C9 . H91 . 0.976 no
C10 . C11 . 1.494(2) yes
C11 . C12 . 1.392(2) yes
C12 . C13 . 1.381(2) yes
C12 . H121 . 0.971 no
C13 . C14 . 1.382(3) yes
C13 . H131 . 0.990 no
C14 . C15 . 1.378(3) yes
C14 . H141 . 0.967 no
C15 . H151 . 0.972 no
C16 . C17 . 1.375(2) yes
C17 . C18 . 1.408(2) yes
C17 . H171 . 0.954 no
C18 . C19 . 1.358(2) yes
C19 . H191 . 0.958 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652681
