#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:50:16 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180520 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/89/7218979.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_7218979
loop_
_publ_author_name
'Peng, Yu-Xin'
'Wang, Na'
'Dai, Yuan'
'Hu, Bin'
'Ma, Bin Bin'
'Huang, Wei'
_publ_section_title
;
 Simultaneous enhancement of fluorescence and solubility by N-alkylation
 and functionalization of 2-(2-thienyl)imidazo[4,5-f][1,10]-phenanthroline
 with heterocyclic bridges
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA12627K
_journal_year                    2014
_chemical_formula_moiety         'C22 H18 Br Cl3 N4 S'
_chemical_formula_sum            'C22 H18 Br Cl3 N4 S'
_chemical_formula_weight         556.72
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.382(5)
_cell_angle_beta                 104.667(5)
_cell_angle_gamma                97.372(5)
_cell_formula_units_Z            2
_cell_length_a                   9.276(3)
_cell_length_b                   10.410(3)
_cell_length_c                   13.153(4)
_cell_measurement_reflns_used    3915
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.239
_cell_measurement_theta_min      2.191
_cell_volume                     1143.6(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (BRUKER 2000)'
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0884
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6035
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    2.257
_exptl_absorpt_correction_T_max  0.8057
_exptl_absorpt_correction_T_min  0.7734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.847
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3915
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0845P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1526
_refine_ls_wR_factor_ref         0.1579
_reflns_number_gt                2946
_reflns_number_total             3915
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra12627k2.cif
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7218979
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.07266(6) 0.78189(5) 0.66271(4) 0.0451(2) Uani 1 1 d . . .
C1 C 0.3421(6) -0.0843(5) 0.1097(4) 0.0398(12) Uani 1 1 d . . .
H1 H 0.3271 -0.1501 0.0400 0.048 Uiso 1 1 calc R . .
C2 C 0.2444(6) 0.0050(5) 0.1178(4) 0.0406(12) Uani 1 1 d . . .
H2 H 0.1643 -0.0035 0.0554 0.049 Uiso 1 1 calc R . .
C3 C 0.2664(5) 0.1064(5) 0.2183(4) 0.0334(11) Uani 1 1 d . . .
H3 H 0.2027 0.1684 0.2253 0.040 Uiso 1 1 calc R . .
C4 C 0.3868(5) 0.1140(4) 0.3101(3) 0.0250(9) Uani 1 1 d . . .
C5 C 0.4218(5) 0.2162(4) 0.4180(3) 0.0237(9) Uani 1 1 d . . .
C6 C 0.5421(5) 0.2205(4) 0.5064(3) 0.0245(9) Uani 1 1 d . . .
C7 C 0.6389(5) 0.1256(4) 0.4969(3) 0.0237(9) Uani 1 1 d . . .
C8 C 0.7655(5) 0.1217(4) 0.5805(3) 0.0278(10) Uani 1 1 d . . .
H8 H 0.7963 0.1896 0.6512 0.033 Uiso 1 1 calc R . .
C9 C 0.8429(5) 0.0206(5) 0.5594(4) 0.0306(10) Uani 1 1 d . . .
H9 H 0.9268 0.0184 0.6148 0.037 Uiso 1 1 calc R . .
C10 C 0.7954(5) -0.0807(4) 0.4532(4) 0.0310(10) Uani 1 1 d . . .
H10 H 0.8468 -0.1521 0.4405 0.037 Uiso 1 1 calc R . .
C11 C 0.6033(5) 0.0196(4) 0.3896(3) 0.0253(9) Uani 1 1 d . . .
C12 C 0.4785(5) 0.0175(4) 0.2969(3) 0.0259(9) Uani 1 1 d . . .
C13 C 0.4208(5) 0.3856(4) 0.5568(3) 0.0247(9) Uani 1 1 d . . .
C14 C 0.3736(5) 0.5046(4) 0.6205(3) 0.0257(9) Uani 1 1 d . . .
C15 C 0.4402(5) 0.6053(4) 0.7227(4) 0.0316(10) Uani 1 1 d . . .
H15 H 0.5345 0.6086 0.7707 0.038 Uiso 1 1 calc R . .
C16 C 0.3520(5) 0.7039(5) 0.7484(4) 0.0334(11) Uani 1 1 d . . .
H16 H 0.3817 0.7790 0.8149 0.040 Uiso 1 1 calc R . .
C17 C 0.2220(5) 0.6780(4) 0.6674(4) 0.0317(10) Uani 1 1 d . . .
C18 C 0.6329(5) 0.3716(4) 0.7142(3) 0.0261(9) Uani 1 1 d . . .
H18A H 0.6570 0.2904 0.7302 0.031 Uiso 1 1 calc R . .
H18B H 0.5753 0.4126 0.7626 0.031 Uiso 1 1 calc R . .
C19 C 0.7803(5) 0.4742(4) 0.7396(3) 0.0273(9) Uani 1 1 d . . .
H19A H 0.8381 0.4332 0.6914 0.033 Uiso 1 1 calc R . .
H19B H 0.7563 0.5555 0.7235 0.033 Uiso 1 1 calc R . .
C20 C 0.8766(6) 0.5165(5) 0.8601(4) 0.0393(12) Uani 1 1 d . . .
H20A H 0.8137 0.5452 0.9078 0.047 Uiso 1 1 calc R . .
H20B H 0.9109 0.4369 0.8731 0.047 Uiso 1 1 calc R . .
C21 C 1.0132(6) 0.6312(6) 0.8931(4) 0.0486(14) Uani 1 1 d . . .
H21A H 1.0763 0.6037 0.8464 0.073 Uiso 1 1 calc R . .
H21B H 1.0706 0.6516 0.9699 0.073 Uiso 1 1 calc R . .
H21C H 0.9801 0.7119 0.8839 0.073 Uiso 1 1 calc R . .
C22 C 0.7176(6) 0.7586(5) 0.1387(4) 0.0511(14) Uani 1 1 d D . .
H22 H 0.6753 0.8212 0.1893 0.077 Uiso 1 1 d R A .
N1 N 0.4561(4) -0.0822(4) 0.1952(3) 0.0335(9) Uani 1 1 d . . .
N2 N 0.6813(4) -0.0802(3) 0.3700(3) 0.0278(8) Uani 1 1 d . . .
N3 N 0.5386(4) 0.3303(3) 0.5969(3) 0.0229(8) Uani 1 1 d . . .
N4 N 0.3479(4) 0.3191(3) 0.4490(3) 0.0257(8) Uani 1 1 d . . .
S1 S 0.20000(13) 0.53142(11) 0.55533(9) 0.0322(3) Uani 1 1 d . . .
Cl1 Cl 0.7554(4) 0.6278(2) 0.1867(2) 0.0652(9) Uani 0.746(7) 1 d PD A 1
Cl2 Cl 0.8967(3) 0.8504(3) 0.13913(19) 0.0648(9) Uani 0.746(7) 1 d PD A 1
Cl3 Cl 0.5933(4) 0.7024(5) 0.0039(2) 0.0930(15) Uani 0.746(7) 1 d PD A 1
Cl1' Cl 0.764(3) 0.8580(11) 0.0733(17) 0.213(13) Uani 0.254(7) 1 d PD A 2
Cl2' Cl 0.5619(10) 0.6196(11) 0.0413(8) 0.092(4) Uani 0.254(7) 1 d PD . 2
Cl3' Cl 0.846(2) 0.687(2) 0.2034(11) 0.244(13) Uani 0.254(7) 1 d PD A 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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 '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
_geom_angle_site_symmetry_3
N1 C1 C2 124.1(4) .
N1 C1 H1 117.9 .
C2 C1 H1 117.9 .
C3 C2 C1 119.5(5) .
C3 C2 H2 120.2 .
C1 C2 H2 120.2 .
C2 C3 C4 118.2(4) .
C2 C3 H3 120.9 .
C4 C3 H3 120.9 .
C3 C4 C12 119.3(4) .
C3 C4 C5 123.1(4) .
C12 C4 C5 117.6(4) .
N4 C5 C6 111.3(4) .
N4 C5 C4 127.3(4) .
C6 C5 C4 121.4(4) .
C5 C6 N3 105.0(4) .
C5 C6 C7 123.0(4) .
N3 C6 C7 132.0(4) .
C8 C7 C6 127.8(4) .
C8 C7 C11 115.7(4) .
C6 C7 C11 116.5(4) .
C9 C8 C7 120.6(4) .
C9 C8 H8 119.7 .
C7 C8 H8 119.7 .
C8 C9 C10 119.1(4) .
C8 C9 H9 120.4 .
C10 C9 H9 120.4 .
N2 C10 C9 123.2(4) .
N2 C10 H10 118.4 .
C9 C10 H10 118.4 .
N2 C11 C7 122.8(4) .
N2 C11 C12 117.2(4) .
C7 C11 C12 120.0(4) .
N1 C12 C4 121.7(4) .
N1 C12 C11 116.9(4) .
C4 C12 C11 121.5(4) .
N4 C13 N3 112.6(4) .
N4 C13 C14 121.0(4) .
N3 C13 C14 126.4(4) .
C15 C14 C13 133.6(4) .
C15 C14 S1 110.5(3) .
C13 C14 S1 115.9(3) .
C14 C15 C16 113.3(4) .
C14 C15 H15 123.3 .
C16 C15 H15 123.3 .
C17 C16 C15 112.5(4) .
C17 C16 H16 123.7 .
C15 C16 H16 123.7 .
C16 C17 S1 112.6(3) .
C16 C17 Br1 127.7(3) .
S1 C17 Br1 119.7(3) .
N3 C18 C19 112.0(3) .
N3 C18 H18A 109.2 .
C19 C18 H18A 109.2 .
N3 C18 H18B 109.2 .
C19 C18 H18B 109.2 .
H18A C18 H18B 107.9 .
C20 C19 C18 111.8(3) .
C20 C19 H19A 109.3 .
C18 C19 H19A 109.3 .
C20 C19 H19B 109.3 .
C18 C19 H19B 109.3 .
H19A C19 H19B 107.9 .
C21 C20 C19 113.7(4) .
C21 C20 H20A 108.8 .
C19 C20 H20A 108.8 .
C21 C20 H20B 108.8 .
C19 C20 H20B 108.8 .
H20A C20 H20B 107.7 .
C20 C21 H21A 109.5 .
C20 C21 H21B 109.5 .
H21A C21 H21B 109.5 .
C20 C21 H21C 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
Cl1' C22 Cl3' 121.3(9) .
Cl1' C22 Cl1 147.4(8) .
Cl3' C22 Cl1 31.3(9) .
Cl1' C22 Cl3 70.0(8) .
Cl3' C22 Cl3 132.0(6) .
Cl1 C22 Cl3 113.4(3) .
Cl1' C22 Cl2' 107.9(8) .
Cl3' C22 Cl2' 106.8(7) .
Cl1 C22 Cl2' 79.3(5) .
Cl3 C22 Cl2' 38.1(4) .
Cl1' C22 Cl2 45.9(9) .
Cl3' C22 Cl2 76.9(10) .
Cl1 C22 Cl2 107.3(3) .
Cl3 C22 Cl2 108.0(3) .
Cl2' C22 Cl2 137.5(5) .
Cl1' C22 H22 98.9 .
Cl3' C22 H22 113.6 .
Cl1 C22 H22 109.3 .
Cl3 C22 H22 109.4 .
Cl2' C22 H22 107.4 .
Cl2 C22 H22 109.4 .
C1 N1 C12 117.1(4) .
C10 N2 C11 118.4(4) .
C13 N3 C6 106.2(3) .
C13 N3 C18 126.2(3) .
C6 N3 C18 127.4(4) .
C13 N4 C5 104.9(4) .
C14 S1 C17 91.1(2) .
C22 Cl2' Cl2' 151.7(10) 2_665
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C17 1.864(5) .
C1 N1 1.326(6) .
C1 C2 1.379(7) .
C1 H1 0.9300 .
C2 C3 1.371(6) .
C2 H2 0.9300 .
C3 C4 1.396(6) .
C3 H3 0.9300 .
C4 C12 1.397(6) .
C4 C5 1.424(5) .
C5 N4 1.361(5) .
C5 C6 1.378(6) .
C6 N3 1.393(5) .
C6 C7 1.418(6) .
C7 C8 1.406(6) .
C7 C11 1.435(5) .
C8 C9 1.350(6) .
C8 H8 0.9300 .
C9 C10 1.395(6) .
C9 H9 0.9300 .
C10 N2 1.318(6) .
C10 H10 0.9300 .
C11 N2 1.340(6) .
C11 C12 1.445(6) .
C12 N1 1.373(5) .
C13 N4 1.325(5) .
C13 N3 1.362(6) .
C13 C14 1.460(6) .
C14 C15 1.364(6) .
C14 S1 1.722(5) .
C15 C16 1.410(7) .
C15 H15 0.9300 .
C16 C17 1.325(7) .
C16 H16 0.9300 .
C17 S1 1.722(4) .
C18 N3 1.467(5) .
C18 C19 1.517(6) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 C20 1.506(6) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 C21 1.498(7) .
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C22 Cl1' 1.612(11) .
C22 Cl3' 1.666(12) .
C22 Cl1 1.703(6) .
C22 Cl3 1.729(6) .
C22 Cl2' 1.800(8) .
C22 Cl2 1.805(6) .
C22 H22 0.9800 .
Cl2' Cl2' 2.390(19) 2_665
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
_geom_torsion_site_symmetry_4
N1 C1 C2 C3 2.2(8) .
C1 C2 C3 C4 -0.9(7) .
C2 C3 C4 C12 -1.1(6) .
C2 C3 C4 C5 178.9(4) .
C3 C4 C5 N4 0.0(6) .
C12 C4 C5 N4 -180.0(4) .
C3 C4 C5 C6 -179.8(4) .
C12 C4 C5 C6 0.2(6) .
N4 C5 C6 N3 1.4(4) .
C4 C5 C6 N3 -178.7(3) .
N4 C5 C6 C7 -179.6(4) .
C4 C5 C6 C7 0.2(6) .
C5 C6 C7 C8 178.9(4) .
N3 C6 C7 C8 -2.5(7) .
C5 C6 C7 C11 -1.7(6) .
N3 C6 C7 C11 177.0(4) .
C6 C7 C8 C9 177.3(4) .
C11 C7 C8 C9 -2.2(6) .
C7 C8 C9 C10 -0.1(6) .
C8 C9 C10 N2 2.7(7) .
C8 C7 C11 N2 2.4(6) .
C6 C7 C11 N2 -177.2(4) .
C8 C7 C11 C12 -177.8(4) .
C6 C7 C11 C12 2.6(6) .
C3 C4 C12 N1 2.0(6) .
C5 C4 C12 N1 -178.0(3) .
C3 C4 C12 C11 -179.1(4) .
C5 C4 C12 C11 0.8(6) .
N2 C11 C12 N1 -3.6(5) .
C7 C11 C12 N1 176.6(3) .
N2 C11 C12 C4 177.5(4) .
C7 C11 C12 C4 -2.3(6) .
N4 C13 C14 C15 -166.1(4) .
N3 C13 C14 C15 13.9(7) .
N4 C13 C14 S1 11.8(5) .
N3 C13 C14 S1 -168.2(3) .
C13 C14 C15 C16 177.9(4) .
S1 C14 C15 C16 -0.2(5) .
C14 C15 C16 C17 0.0(6) .
C15 C16 C17 S1 0.1(5) .
C15 C16 C17 Br1 -178.3(3) .
N3 C18 C19 C20 179.9(4) .
C18 C19 C20 C21 -172.4(4) .
C2 C1 N1 C12 -1.3(7) .
C4 C12 N1 C1 -0.8(6) .
C11 C12 N1 C1 -179.7(4) .
C9 C10 N2 C11 -2.6(6) .
C7 C11 N2 C10 0.0(6) .
C12 C11 N2 C10 -179.9(4) .
N4 C13 N3 C6 0.9(4) .
C14 C13 N3 C6 -179.1(4) .
N4 C13 N3 C18 -174.2(3) .
C14 C13 N3 C18 5.8(6) .
C5 C6 N3 C13 -1.4(4) .
C7 C6 N3 C13 179.8(4) .
C5 C6 N3 C18 173.6(4) .
C7 C6 N3 C18 -5.2(7) .
C19 C18 N3 C13 -96.1(5) .
C19 C18 N3 C6 89.8(5) .
N3 C13 N4 C5 0.0(4) .
C14 C13 N4 C5 180.0(4) .
C6 C5 N4 C13 -0.9(4) .
C4 C5 N4 C13 179.3(4) .
C15 C14 S1 C17 0.2(3) .
C13 C14 S1 C17 -178.2(3) .
C16 C17 S1 C14 -0.2(4) .
Br1 C17 S1 C14 178.4(3) .
Cl1' C22 Cl2' Cl2' 135.2(15) 2_665
Cl3' C22 Cl2' Cl2' 3.2(18) 2_665
Cl1 C22 Cl2' Cl2' -12.0(17) 2_665
Cl3 C22 Cl2' Cl2' 141.6(19) 2_665
Cl2 C22 Cl2' Cl2' 92(2) 2_665
