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#$Date: 2016-03-21 03:50:56 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178447 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/68/4026814.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_4026814
loop_
_publ_author_name
'Jaebum Lim'
'Thomas A. Albright'
'Benjamin R. Martin'
'Ognjen Š. Miljanić'
_publ_contact_author_email       miljanic@uh.edu
_publ_contact_author_name        'Ognjen S. Miljanic'
_publ_section_title
;
 Benzobisoxazole Cruciforms: Heterocyclic Fluorophores with Spatially
 Separated Frontier Molecular Orbitals
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10207
_journal_page_last               10219
_journal_paper_doi               10.1021/jo202107w
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C38 H28 N6 O2, C H2 Cl2'
_chemical_formula_sum            'C39 H30 Cl2 N6 O2'
_chemical_formula_weight         685.59
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.933(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.440(4)
_cell_length_b                   5.8011(11)
_cell_length_c                   30.416(6)
_cell_measurement_reflns_used    78
_cell_measurement_temperature    223(2)
_cell_volume                     3411.4(12)
_computing_cell_refinement       'Process-Auto (Rigaku, 2006)'
_computing_data_collection       'SCXmini (Rigaku, 2006)'
_computing_data_reduction        'Process-Auto (Rigaku, 2006)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1109
_diffrn_reflns_av_sigmaI/netI    0.1687
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            11258
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.67
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_correction_T_min  0.8342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 2001)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.908
_refine_ls_R_factor_all          0.2044
_refine_ls_R_factor_gt           0.0659
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0673P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1477
_refine_ls_wR_factor_ref         0.1821
_reflns_number_gt                1361
_reflns_number_total             3842
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202107w_si_004.cif
_cod_data_source_block           LJB-47-3_in_C2/c
_cod_original_cell_volume        3411.3(11)
_cod_database_code               4026814
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.47858(9) 0.9583(3) 0.19982(5) 0.1374(8) Uani 1 1 d .
O1 O 0.33433(12) 0.5835(4) 0.04887(7) 0.0398(7) Uani 1 1 d .
N1 N 0.31306(15) 0.6138(5) -0.02867(8) 0.0376(8) Uani 1 1 d .
N2 N 0.3713(2) 0.3996(6) 0.33589(10) 0.0747(12) Uani 1 1 d .
C1 C 0.4056(3) 0.6073(8) 0.35677(14) 0.116(2) Uani 1 1 d .
H1A H 0.4481 0.6249 0.3495 0.140 Uiso 1 1 calc R
H1B H 0.4161 0.5990 0.3902 0.140 Uiso 1 1 calc R
H1C H 0.3756 0.7383 0.3447 0.140 Uiso 1 1 calc R
C2 C 0.3451(2) 0.2481(8) 0.36419(12) 0.0831(16) Uani 1 1 d .
H2A H 0.3688 0.1010 0.3678 0.100 Uiso 1 1 calc R
H2B H 0.2959 0.2244 0.3492 0.100 Uiso 1 1 calc R
H2C H 0.3530 0.3173 0.3945 0.100 Uiso 1 1 calc R
C3 C 0.3534(2) 0.3632(7) 0.28843(11) 0.0524(11) Uani 1 1 d .
C4 C 0.3201(2) 0.1628(7) 0.26778(11) 0.0532(12) Uani 1 1 d .
H4 H 0.3096 0.0483 0.2863 0.064 Uiso 1 1 calc R
C5 C 0.3020(2) 0.1299(7) 0.22036(11) 0.0505(11) Uani 1 1 d .
H5 H 0.2793 -0.0070 0.2074 0.061 Uiso 1 1 calc R
C6 C 0.31637(19) 0.2918(6) 0.19111(10) 0.0420(10) Uani 1 1 d .
C7 C 0.3499(2) 0.4917(7) 0.21185(12) 0.0605(12) Uani 1 1 d .
H7 H 0.3600 0.6060 0.1931 0.073 Uiso 1 1 calc R
C8 C 0.3687(2) 0.5266(7) 0.25894(12) 0.0677(14) Uani 1 1 d .
H8 H 0.3922 0.6625 0.2718 0.081 Uiso 1 1 calc R
C9 C 0.29705(19) 0.2599(6) 0.14162(11) 0.0440(10) Uani 1 1 d .
C10 C 0.28065(18) 0.2384(6) 0.10069(11) 0.0406(9) Uani 1 1 d .
C11 C 0.26484(18) 0.2379(6) 0.05105(10) 0.0358(9) Uani 1 1 d .
C12 C 0.29072(17) 0.4046(6) 0.02810(10) 0.0330(9) Uani 1 1 d .
C13 C 0.34499(19) 0.6999(6) 0.01208(11) 0.0407(10) Uani 1 1 d .
C14 C 0.39070(18) 0.9002(6) 0.02349(11) 0.0378(9) Uani 1 1 d .
C15 C 0.40151(19) 1.0371(6) -0.01103(11) 0.0415(10) Uani 1 1 d .
H15 H 0.3801 0.9999 -0.0425 0.050 Uiso 1 1 calc R
C16 C 0.44356(19) 1.2263(6) 0.00109(12) 0.0470(10) Uani 1 1 d .
H16 H 0.4501 1.3152 -0.0230 0.056 Uiso 1 1 calc R
N3 N 0.47606(16) 1.2936(5) 0.04486(10) 0.0538(9) Uani 1 1 d .
C18 C 0.4653(2) 1.1600(7) 0.07805(13) 0.0603(12) Uani 1 1 d .
H18 H 0.4874 1.2018 0.1092 0.072 Uiso 1 1 calc R
C19 C 0.4239(2) 0.9661(7) 0.06958(11) 0.0527(11) Uani 1 1 d .
H19 H 0.4182 0.8801 0.0943 0.063 Uiso 1 1 calc R
C20 C 0.5000 1.1129(14) 0.2500 0.111(3) Uani 1 2 d S
H20A H 0.4609 1.2130 0.2489 0.133 Uiso 0.50 1 calc PR
H20B H 0.5391 1.2130 0.2511 0.133 Uiso 0.50 1 calc PR
C21 C 0.27754(18) 0.4235(6) -0.01989(10) 0.0350(9) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
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'
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
C12 O1 C13 104.2(2) . .
C13 N1 C21 104.7(3) . .
C3 N2 C1 121.0(4) . .
C3 N2 C2 120.2(4) . .
C1 N2 C2 117.9(3) . .
N2 C1 H1A 109.5 . .
N2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
N2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N2 C2 H2A 109.5 . .
N2 C2 H2B 109.5 . .
H2A C2 H2B 109.5 . .
N2 C2 H2C 109.5 . .
H2A C2 H2C 109.5 . .
H2B C2 H2C 109.5 . .
N2 C3 C4 121.5(4) . .
N2 C3 C8 121.5(4) . .
C4 C3 C8 116.9(3) . .
C5 C4 C3 120.9(3) . .
C5 C4 H4 119.6 . .
C3 C4 H4 119.6 . .
C4 C5 C6 122.4(4) . .
C4 C5 H5 118.8 . .
C6 C5 H5 118.8 . .
C5 C6 C7 116.7(3) . .
C5 C6 C9 122.7(3) . .
C7 C6 C9 120.6(3) . .
C8 C7 C6 121.8(4) . .
C8 C7 H7 119.1 . .
C6 C7 H7 119.1 . .
C7 C8 C3 121.4(4) . .
C7 C8 H8 119.3 . .
C3 C8 H8 119.3 . .
C10 C9 C6 178.6(4) . .
C9 C10 C11 173.2(4) . .
C12 C11 C21 112.0(3) . 7
C12 C11 C10 122.1(3) . .
C21 C11 C10 125.9(3) 7 .
O1 C12 C11 125.9(3) . .
O1 C12 C21 107.2(3) . .
C11 C12 C21 126.9(3) . .
N1 C13 O1 115.0(3) . .
N1 C13 C14 128.1(3) . .
O1 C13 C14 116.9(3) . .
C15 C14 C19 117.2(4) . .
C15 C14 C13 121.4(3) . .
C19 C14 C13 121.4(3) . .
C16 C15 C14 119.6(3) . .
C16 C15 H15 120.2 . .
C14 C15 H15 120.2 . .
N3 C16 C15 124.6(3) . .
N3 C16 H16 117.7 . .
C15 C16 H16 117.7 . .
C16 N3 C18 115.4(3) . .
N3 C18 C19 124.6(3) . .
N3 C18 H18 117.7 . .
C19 C18 H18 117.7 . .
C18 C19 C14 118.6(3) . .
C18 C19 H19 120.7 . .
C14 C19 H19 120.7 . .
Cl1 C20 Cl1 116.3(5) . 2_655
Cl1 C20 H20A 108.2 . .
Cl1 C20 H20A 108.2 2_655 .
Cl1 C20 H20B 108.2 . .
Cl1 C20 H20B 108.2 2_655 .
H20A C20 H20B 107.4 . .
N1 C21 C12 109.0(3) . .
N1 C21 C11 129.9(3) . 7
C12 C21 C11 121.1(3) . 7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C20 1.701(5) .
O1 C12 1.380(4) .
O1 C13 1.383(4) .
N1 C13 1.299(4) .
N1 C21 1.394(4) .
N2 C3 1.385(4) .
N2 C1 1.434(5) .
N2 C2 1.449(5) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C1 H1C 0.9700 .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C2 H2C 0.9700 .
C3 C4 1.390(5) .
C3 C8 1.408(5) .
C4 C5 1.381(4) .
C4 H4 0.9400 .
C5 C6 1.389(5) .
C5 H5 0.9400 .
C6 C7 1.390(4) .
C6 C9 1.439(4) .
C7 C8 1.372(5) .
C7 H7 0.9400 .
C8 H8 0.9400 .
C9 C10 1.186(4) .
C10 C11 1.438(4) .
C11 C12 1.393(4) .
C11 C21 1.412(4) 7
C12 C21 1.400(4) .
C13 C14 1.461(5) .
C14 C15 1.390(4) .
C14 C19 1.398(4) .
C15 C16 1.369(5) .
C15 H15 0.9400 .
C16 N3 1.339(4) .
C16 H16 0.9400 .
N3 C18 1.346(5) .
C18 C19 1.380(5) .
C18 H18 0.9400 .
C19 H19 0.9400 .
C20 Cl1 1.701(4) 2_655
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C21 C11 1.412(4) 7
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_1
_geom_torsion_site_symmetry_4
C1 N2 C3 C4 -179.9(4) . .
C2 N2 C3 C4 -10.7(6) . .
C1 N2 C3 C8 0.6(7) . .
C2 N2 C3 C8 169.7(4) . .
N2 C3 C4 C5 179.4(4) . .
C8 C3 C4 C5 -1.0(6) . .
C3 C4 C5 C6 0.4(6) . .
C4 C5 C6 C7 -0.2(6) . .
C4 C5 C6 C9 -179.3(4) . .
C5 C6 C7 C8 0.7(6) . .
C9 C6 C7 C8 179.8(4) . .
C6 C7 C8 C3 -1.4(7) . .
N2 C3 C8 C7 -178.9(4) . .
C4 C3 C8 C7 1.5(7) . .
C5 C6 C9 C10 136(17) . .
C7 C6 C9 C10 -43(18) . .
C6 C9 C10 C11 46(20) . .
C9 C10 C11 C12 6(4) . .
C9 C10 C11 C21 -174(3) . 7
C13 O1 C12 C11 -179.9(3) . .
C13 O1 C12 C21 -0.1(3) . .
C21 C11 C12 O1 -179.1(3) 7 .
C10 C11 C12 O1 1.2(6) . .
C21 C11 C12 C21 1.2(6) 7 .
C10 C11 C12 C21 -178.5(3) . .
C21 N1 C13 O1 -0.1(4) . .
C21 N1 C13 C14 179.2(3) . .
C12 O1 C13 N1 0.1(4) . .
C12 O1 C13 C14 -179.2(3) . .
N1 C13 C14 C15 4.7(6) . .
O1 C13 C14 C15 -176.1(3) . .
N1 C13 C14 C19 -177.1(4) . .
O1 C13 C14 C19 2.1(5) . .
C19 C14 C15 C16 0.3(5) . .
C13 C14 C15 C16 178.6(3) . .
C14 C15 C16 N3 -0.3(6) . .
C15 C16 N3 C18 0.3(6) . .
C16 N3 C18 C19 -0.3(6) . .
N3 C18 C19 C14 0.3(7) . .
C15 C14 C19 C18 -0.3(6) . .
C13 C14 C19 C18 -178.6(4) . .
C13 N1 C21 C12 0.0(4) . .
C13 N1 C21 C11 -178.7(4) . 7
O1 C12 C21 N1 0.1(4) . .
C11 C12 C21 N1 179.8(3) . .
O1 C12 C21 C11 178.9(3) . 7
C11 C12 C21 C11 -1.3(6) . 7
