#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/89/1518949.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_1518949
loop_
_publ_author_name
'He, Bo'
'Dai, Jing'
'Zherebetskyy, Danylo'
'Chen, Teresa L.'
'Zhang, Benjamin A.'
'Teat, Simon J.'
'Zhang, Qichun'
'Wang, Linwang'
'Liu, Yi'
_publ_section_title
;
 A divergent route to core- and peripherally functionalized diazacoronenes
 that act as colorimetric and fluorescence proton sensors
;
_journal_issue                   5
_journal_name_full               'Chem. Sci.'
_journal_page_first              3180
_journal_paper_doi               10.1039/C5SC00304K
_journal_volume                  6
_journal_year                    2015
_chemical_formula_sum            'C46 H46 N2 S2'
_chemical_formula_weight         690.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2014-10-31 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.545(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   23.6399(19)
_cell_length_b                   5.2070(3)
_cell_length_c                   15.0420(10)
_cell_measurement_reflns_used    5749
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.87
_cell_measurement_theta_min      2.85
_cell_volume                     1765.4(2)
_computing_cell_refinement       'Bruker SAINT v8.34a'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker SAINT v8.34a'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 2014/3 beta'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 with PHOTON 100 detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7749
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16462
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.011
_diffrn_reflns_theta_max         25.011
_diffrn_reflns_theta_min         2.953
_diffrn_source                   'Advanced Light Source station 11.3.1'
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/3 Bruker AXS Madison WI USA'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0061(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2388
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0661
_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)+(0.0520P)²+3.6058P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1749
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1666
_reflns_number_total             2388
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5sc00304k2.cif
_cod_data_source_block           seh_bac_a
_cod_depositor_comments
'Adding full bibliography for 1518949--1518951.cif.'
_cod_database_code               1518949
#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   0.966
_shelx_estimated_absorpt_t_max   0.999
_shelxl_version_number           2014/6
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S1 S 0.73630(7) 0.1925(2) 0.64656(9) 0.0672(5) Uani 1 1 d . . . . .
N1 N 0.6400(2) 0.3561(6) 0.5267(3) 0.0532(11) Uani 1 1 d . . . . .
C1 C 0.6591(2) 0.1879(8) 0.5939(3) 0.0535(13) Uani 1 1 d . . . . .
C2 C 0.6195(3) 0.0057(7) 0.6196(3) 0.0495(13) Uani 1 1 d . . . . .
C3 C 0.5610(2) -0.0002(7) 0.5614(3) 0.0477(13) Uani 1 1 d . . . . .
C4 C 0.5415(2) 0.1774(7) 0.4868(3) 0.0469(13) Uani 1 1 d . . . . .
C5 C 0.4823(2) 0.1818(7) 0.4264(3) 0.0475(13) Uani 1 1 d . . . . .
C6 C 0.4642(2) 0.3671(7) 0.3554(3) 0.0487(13) Uani 1 1 d . . . . .
C7 C 0.5072(3) 0.5492(8) 0.3462(3) 0.0511(14) Uani 1 1 d . . . . .
H7A H 0.4958 0.6768 0.2990 0.061 Uiso 1 1 calc R U . . .
C8 C 0.5635(3) 0.5449(8) 0.4025(3) 0.0526(14) Uani 1 1 d . . . . .
H8A H 0.5909 0.6690 0.3943 0.063 Uiso 1 1 calc R U . . .
C9 C 0.5826(3) 0.3582(7) 0.4742(3) 0.0483(13) Uani 1 1 d . . . . .
C10 C 0.4048(3) 0.3634(7) 0.2934(3) 0.0511(14) Uani 1 1 d . . . . .
C11 C 0.3857(3) 0.5424(8) 0.2196(3) 0.0569(14) Uani 1 1 d . . . . .
H11A H 0.4120 0.6762 0.2149 0.068 Uiso 1 1 calc R U . . .
C12 C 0.3313(3) 0.5308(9) 0.1553(4) 0.0618(15) Uani 1 1 d . . . . .
H12A H 0.3200 0.6576 0.1078 0.074 Uiso 1 1 calc R U . . .
C13 C 0.2919(3) 0.3342(9) 0.1584(3) 0.0633(14) Uani 1 1 d . . . . .
H13A H 0.2546 0.3205 0.1119 0.076 Uiso 1 1 calc R U . . .
C14 C 0.3085(3) 0.1600(9) 0.2307(3) 0.0595(14) Uani 1 1 d . . . . .
H14A H 0.2817 0.0261 0.2330 0.071 Uiso 1 1 calc R U . . .
C15 C 0.3631(2) 0.1713(8) 0.3012(3) 0.0523(13) Uani 1 1 d . . . . .
C16 C 0.7586(3) 0.4529(11) 0.5847(3) 0.0767(17) Uani 1 1 d . . . . .
H16C H 0.7431 0.4226 0.5166 0.092 Uiso 0.4 1 calc R U P A 2
H16D H 0.7419 0.6168 0.5988 0.092 Uiso 0.4 1 calc R U P A 2
H16A H 0.7431 0.4226 0.5166 0.092 Uiso 0.6 1 calc R U P B 1
H16B H 0.7419 0.6168 0.5988 0.092 Uiso 0.6 1 calc R U P B 1
C17 C 0.8257(3) 0.4693(15) 0.6141(4) 0.097(2) Uani 1 1 d . . . . .
H17B H 0.8295 0.6328 0.5815 0.116 Uiso 0.4 1 calc R U P C 2
H17A H 0.8368 0.2835 0.6207 0.116 Uiso 0.6 1 calc R U P D 1
C18 C 0.8508(3) 0.5607(13) 0.7120(4) 0.095(2) Uani 1 1 d . U . . .
H18A H 0.8334 0.7320 0.7152 0.114 Uiso 1 1 calc R U . . .
H18B H 0.8353 0.4448 0.7514 0.114 Uiso 1 1 calc R U . . .
C19 C 0.9124(4) 0.584(2) 0.7561(5) 0.156(3) Uani 1 1 d . U . . .
H19A H 0.9296 0.4152 0.7477 0.187 Uiso 1 1 calc R U . . .
H19B H 0.9268 0.7076 0.7180 0.187 Uiso 1 1 calc R U . . .
C20 C 0.9400(4) 0.653(2) 0.8491(5) 0.148(3) Uani 1 1 d D U . . .
H20C H 0.9173 0.5729 0.8874 0.177 Uiso 0.4 1 calc R U P E 2
H20D H 0.9356 0.8415 0.8537 0.177 Uiso 0.4 1 calc R U P E 2
H20A H 0.9494 0.4877 0.8826 0.177 Uiso 0.6 1 calc R U P F 1
H20B H 0.9078 0.7303 0.8698 0.177 Uiso 0.6 1 calc R U P F 1
C21 C 0.9909(11) 0.813(6) 0.891(2) 0.196(12) Uani 0.4 1 d D U P G 1
H21A H 0.9978 0.8197 0.9587 0.294 Uiso 0.4 1 calc R U P G 1
H21B H 1.0258 0.7403 0.8782 0.294 Uiso 0.4 1 calc R U P G 1
H21C H 0.9836 0.9865 0.8652 0.294 Uiso 0.4 1 calc R U P G 1
C21' C 1.0024(6) 0.591(4) 0.8922(13) 0.170(8) Uani 0.6 1 d D U P G 2
H21D H 1.0150 0.6525 0.9568 0.256 Uiso 0.6 1 calc R U P G 2
H21E H 1.0079 0.4050 0.8913 0.256 Uiso 0.6 1 calc R U P G 2
H21F H 1.0263 0.6752 0.8574 0.256 Uiso 0.6 1 calc R U P G 2
C22 C 0.8519(5) 0.553(2) 0.5373(6) 0.085(3) Uani 0.6 1 d . . P H 1
H22A H 0.8956 0.5677 0.5639 0.102 Uiso 0.6 1 calc R U P H 1
H22B H 0.8363 0.7251 0.5144 0.102 Uiso 0.6 1 calc R U P H 1
C22' C 0.8483(7) 0.321(3) 0.5694(11) 0.084(5) Uani 0.4 1 d . . P H 2
H22C H 0.8343 0.1459 0.5773 0.101 Uiso 0.4 1 calc R U P H 2
H22D H 0.8917 0.3232 0.6002 0.101 Uiso 0.4 1 calc R U P H 2
C23 C 0.8375(3) 0.3646(16) 0.4544(5) 0.124(3) Uani 1 1 d . . . . .
H23D H 0.8585 0.2305 0.4313 0.187 Uiso 0.4 1 calc R U P H 2
H23E H 0.7950 0.3549 0.4210 0.187 Uiso 0.4 1 calc R U P H 2
H23F H 0.8527 0.5334 0.4441 0.187 Uiso 0.4 1 calc R U P H 2
H23A H 0.8553 0.4269 0.4074 0.187 Uiso 0.6 1 calc R U P H 1
H23B H 0.8536 0.1948 0.4763 0.187 Uiso 0.6 1 calc R U P H 1
H23C H 0.7944 0.3522 0.4268 0.187 Uiso 0.6 1 calc R U P H 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020
'XDISP Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'
H H 0.0000 0.0000
'XDISP Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'
N N 0.0076 0.0040
'XDISP Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'
S S 0.1431 0.1480
'XDISP Program in WinGX L.Kissel & R.H.Pratt Acta Cryst A46 170 1990'
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_1
_geom_angle_site_symmetry_3
C1 S1 C16 101.6(2) . .
C1 N1 C9 120.6(4) . .
N1 C1 C2 122.6(5) . .
N1 C1 S1 114.1(4) . .
C2 C1 S1 123.3(4) . .
C3 C2 C15 118.6(4) . 3_656
C3 C2 C1 116.0(4) . .
C15 C2 C1 125.3(5) 3_656 .
C2 C3 C4 120.4(4) . .
C2 C3 C5 122.7(4) . 3_656
C4 C3 C5 116.9(5) . 3_656
C9 C4 C3 118.0(5) . .
C9 C4 C5 119.4(4) . .
C3 C4 C5 122.6(4) . .
C6 C5 C4 120.7(4) . .
C6 C5 C3 118.7(5) . 3_656
C4 C5 C3 120.5(4) . 3_656
C5 C6 C7 117.9(5) . .
C5 C6 C10 119.9(4) . .
C7 C6 C10 122.2(4) . .
C8 C7 C6 121.7(4) . .
C8 C7 H7A 119.1 . .
C6 C7 H7A 119.1 . .
C7 C8 C9 121.2(5) . .
C7 C8 H8A 119.4 . .
C9 C8 H8A 119.4 . .
N1 C9 C4 122.0(4) . .
N1 C9 C8 119.0(4) . .
C4 C9 C8 119.0(5) . .
C11 C10 C6 121.4(4) . .
C11 C10 C15 117.3(5) . .
C6 C10 C15 121.3(4) . .
C12 C11 C10 122.6(5) . .
C12 C11 H11A 118.7 . .
C10 C11 H11A 118.7 . .
C11 C12 C13 120.5(5) . .
C11 C12 H12A 119.8 . .
C13 C12 H12A 119.8 . .
C14 C13 C12 118.4(5) . .
C14 C13 H13A 120.8 . .
C12 C13 H13A 120.8 . .
C13 C14 C15 123.1(5) . .
C13 C14 H14A 118.5 . .
C15 C14 H14A 118.5 . .
C14 C15 C10 117.8(4) . .
C14 C15 C2 123.8(4) . 3_656
C10 C15 C2 118.3(5) . 3_656
C17 C16 S1 109.5(4) . .
C17 C16 H16C 109.8 . .
S1 C16 H16C 109.8 . .
C17 C16 H16D 109.8 . .
S1 C16 H16D 109.8 . .
H16C C16 H16D 108.2 . .
C17 C16 H16A 109.8 . .
S1 C16 H16A 109.8 . .
C17 C16 H16B 109.8 . .
S1 C16 H16B 109.8 . .
H16A C16 H16B 108.2 . .
C22' C17 C18 128.6(11) . .
C22' C17 C16 112.9(9) . .
C18 C17 C16 112.2(5) . .
C18 C17 C22 121.6(6) . .
C16 C17 C22 115.0(6) . .
C22' C17 H17B 98.4 . .
C18 C17 H17B 98.4 . .
C16 C17 H17B 98.4 . .
C18 C17 H17A 101.3 . .
C16 C17 H17A 101.3 . .
C22 C17 H17A 101.3 . .
C19 C18 C17 122.6(6) . .
C19 C18 H18A 106.7 . .
C17 C18 H18A 106.7 . .
C19 C18 H18B 106.7 . .
C17 C18 H18B 106.7 . .
H18A C18 H18B 106.6 . .
C20 C19 C18 126.5(8) . .
C20 C19 H19A 105.7 . .
C18 C19 H19A 105.7 . .
C20 C19 H19B 105.7 . .
C18 C19 H19B 105.7 . .
H19A C19 H19B 106.1 . .
C19 C20 C21 131.6(17) . .
C19 C20 C21' 119.4(12) . .
C19 C20 H20C 107.5 . .
C21' C20 H20C 107.5 . .
C19 C20 H20D 107.5 . .
C21' C20 H20D 107.5 . .
H20C C20 H20D 107.0 . .
C19 C20 H20A 104.4 . .
C21 C20 H20A 104.4 . .
C19 C20 H20B 104.4 . .
C21 C20 H20B 104.4 . .
H20A C20 H20B 105.6 . .
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 . .
C20 C21' H21D 109.5 . .
C20 C21' H21E 109.5 . .
H21D C21' H21E 109.5 . .
C20 C21' H21F 109.5 . .
H21D C21' H21F 109.5 . .
H21E C21' H21F 109.5 . .
C17 C22 C23 112.8(8) . .
C17 C22 H22A 109.0 . .
C23 C22 H22A 109.0 . .
C17 C22 H22B 109.0 . .
C23 C22 H22B 109.0 . .
H22A C22 H22B 107.8 . .
C17 C22' C23 121.0(12) . .
C17 C22' H22C 107.1 . .
C23 C22' H22C 107.1 . .
C17 C22' H22D 107.1 . .
C23 C22' H22D 107.1 . .
H22C C22' H22D 106.8 . .
C22' C23 H23D 109.5 . .
C22' C23 H23E 109.5 . .
H23D C23 H23E 109.5 . .
C22' C23 H23F 109.5 . .
H23D C23 H23F 109.5 . .
H23E C23 H23F 109.5 . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.758(5) .
S1 C16 1.810(5) .
N1 C1 1.310(5) .
N1 C9 1.348(6) .
C1 C2 1.464(6) .
C2 C3 1.396(6) .
C2 C15 1.463(6) 3_656
C3 C4 1.420(6) .
C3 C5 1.445(6) 3_656
C4 C9 1.406(6) .
C4 C5 1.420(6) .
C5 C6 1.407(6) .
C5 C3 1.445(6) 3_656
C6 C7 1.427(6) .
C6 C10 1.433(7) .
C7 C8 1.345(6) .
C7 H7A 0.9500 .
C8 C9 1.420(6) .
C8 H8A 0.9500 .
C10 C11 1.415(6) .
C10 C15 1.434(6) .
C11 C12 1.358(7) .
C11 H11A 0.9500 .
C12 C13 1.394(7) .
C12 H12A 0.9500 .
C13 C14 1.379(6) .
C13 H13A 0.9500 .
C14 C15 1.403(7) .
C14 H14A 0.9500 .
C15 C2 1.464(6) 3_656
C16 C17 1.515(8) .
C16 H16C 0.9900 .
C16 H16D 0.9900 .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 C22' 1.244(13) .
C17 C18 1.490(8) .
C17 C22 1.531(10) .
C17 H17B 1.0000 .
C17 H17A 1.0000 .
C18 C19 1.410(9) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.402(9) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.441(13) .
C20 C21' 1.457(12) .
C20 H20C 0.9900 .
C20 H20D 0.9900 .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C21' H21D 0.9800 .
C21' H21E 0.9800 .
C21' H21F 0.9800 .
C22 C23 1.542(11) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C22' C23 1.686(15) .
C22' H22C 0.9900 .
C22' H22D 0.9900 .
C23 H23D 0.9800 .
C23 H23E 0.9800 .
C23 H23F 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
