#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:47:24 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178444 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/65/4026506.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_4026506
loop_
_publ_author_name
'Teh-Chang Chou'
'Ren-Tsung Wu'
'Kung-Ching Liao'
'Chun-Hung Wang'
_publ_section_title
;
 N-1- and N-2-Anthryl Succinimide Derivatives: C-N Bond Rotational
 Behaviors and Fluorescence Energy Transfer
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6813
_journal_page_last               6818
_journal_paper_doi               10.1021/jo200665v
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C24 H18 Cl3 N O2'
_chemical_formula_weight         458.74
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.114(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.0259(6)
_cell_length_b                   6.2593(3)
_cell_length_c                   24.8603(11)
_cell_measurement_reflns_used    12225
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      1.49
_cell_volume                     2125.62(17)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       'NONIUS COLLECT'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'NONIUS KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_sigmaI/netI    0.0801
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12225
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.453
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            light-brown
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4825
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0559
_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)+(0.1018P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1722
_reflns_number_gt                2783
_reflns_number_total             4825
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200665v_si_004.cif
_cod_data_source_block           ic14277
_cod_database_code               4026506
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.47567(13) 0.8403(3) 0.77222(8) 0.0440(5) Uani 1 1 d .
O2 O 0.69901(13) 0.4005(3) 0.87973(7) 0.0370(4) Uani 1 1 d .
N1 N 0.60253(14) 0.6358(3) 0.81996(8) 0.0271(5) Uani 1 1 d .
C1 C 0.50400(18) 0.6909(4) 0.80217(10) 0.0317(6) Uani 1 1 d .
C2 C 0.44463(18) 0.5384(4) 0.82776(9) 0.0315(6) Uani 1 1 d .
H2 H 0.3981 0.4564 0.7986 0.038 Uiso 1 1 calc R
C3 C 0.52041(18) 0.3876(4) 0.86332(10) 0.0321(6) Uani 1 1 d .
H3 H 0.5092 0.2361 0.8507 0.038 Uiso 1 1 calc R
C4 C 0.61817(18) 0.4671(4) 0.85665(9) 0.0286(5) Uani 1 1 d .
C5 C 0.39039(19) 0.6375(4) 0.86992(11) 0.0377(6) Uani 1 1 d .
H5 H 0.3258 0.7064 0.8540 0.045 Uiso 1 1 calc R
C6 C 0.4648(2) 0.7730(5) 0.90859(11) 0.0450(7) Uani 1 1 d .
H6 H 0.4650 0.9246 0.9107 0.054 Uiso 1 1 calc R
C7 C 0.5301(2) 0.6427(5) 0.93918(10) 0.0417(7) Uani 1 1 d .
H7 H 0.5857 0.6846 0.9667 0.050 Uiso 1 1 calc R
C8 C 0.50061(19) 0.4183(4) 0.92248(10) 0.0361(6) Uani 1 1 d .
H8 H 0.5272 0.3047 0.9501 0.043 Uiso 1 1 calc R
C9 C 0.38843(19) 0.4412(4) 0.90685(11) 0.0382(6) Uani 1 1 d .
H9A H 0.3553 0.3165 0.8862 0.046 Uiso 1 1 calc R
H9B H 0.3601 0.4724 0.9390 0.046 Uiso 1 1 calc R
C10 C 0.67797(16) 0.7429(4) 0.79953(9) 0.0288(5) Uani 1 1 d .
C11 C 0.70728(17) 0.9484(4) 0.82015(10) 0.0314(6) Uani 1 1 d .
H11 H 0.6804 1.0089 0.8485 0.038 Uiso 1 1 calc R
C12 C 0.77392(18) 1.0596(4) 0.79944(10) 0.0330(6) Uani 1 1 d .
H12 H 0.7934 1.1979 0.8135 0.040 Uiso 1 1 calc R
C13 C 0.81505(17) 0.9715(4) 0.75687(10) 0.0301(6) Uani 1 1 d .
C14 C 0.88453(17) 1.0810(4) 0.73519(10) 0.0319(6) Uani 1 1 d .
H14 H 0.9045 1.2197 0.7487 0.038 Uiso 1 1 calc R
C15 C 0.92541(17) 0.9912(4) 0.69398(10) 0.0325(6) Uani 1 1 d .
C16 C 0.99936(18) 1.1000(4) 0.67309(11) 0.0383(6) Uani 1 1 d .
H16 H 1.0203 1.2385 0.6864 0.046 Uiso 1 1 calc R
C17 C 1.0396(2) 1.0048(5) 0.63411(11) 0.0471(7) Uani 1 1 d .
H17 H 1.0895 1.0766 0.6210 0.057 Uiso 1 1 calc R
C18 C 1.0082(2) 0.8018(5) 0.61315(11) 0.0471(7) Uani 1 1 d .
H18 H 1.0365 0.7393 0.5856 0.057 Uiso 1 1 calc R
C19 C 0.93793(19) 0.6935(5) 0.63168(11) 0.0404(7) Uani 1 1 d .
H19 H 0.9172 0.5570 0.6168 0.049 Uiso 1 1 calc R
C20 C 0.89535(17) 0.7839(4) 0.67325(10) 0.0330(6) Uani 1 1 d .
C21 C 0.82545(17) 0.6735(4) 0.69499(10) 0.0308(6) Uani 1 1 d .
H21 H 0.8049 0.5355 0.6811 0.037 Uiso 1 1 calc R
C22 C 0.78530(16) 0.7619(4) 0.73658(9) 0.0286(5) Uani 1 1 d .
C23 C 0.71479(17) 0.6505(4) 0.75950(9) 0.0286(5) Uani 1 1 d .
H23 H 0.6939 0.5116 0.7466 0.034 Uiso 1 1 calc R
C24 C 0.7924(2) 1.1155(5) 0.98438(12) 0.0469(7) Uani 1 1 d .
H24 H 0.7623 1.1873 0.9486 0.056 Uiso 1 1 calc R
Cl1 Cl 0.70032(6) 1.07132(15) 1.02062(4) 0.0694(3) Uani 1 1 d .
Cl2 Cl 0.84222(9) 0.87544(17) 0.96998(4) 0.0924(4) Uani 1 1 d .
Cl3 Cl 0.88099(8) 1.28424(18) 1.02233(4) 0.0878(4) 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
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C4 N1 C1 113.3(2)
C4 N1 C10 124.77(19)
C1 N1 C10 121.84(19)
O1 C1 N1 123.5(2)
O1 C1 C2 128.2(2)
N1 C1 C2 108.3(2)
C1 C2 C3 104.8(2)
C1 C2 C5 115.8(2)
C3 C2 C5 103.69(18)
C4 C3 C2 105.2(2)
C4 C3 C8 115.0(2)
C2 C3 C8 102.53(19)
O2 C4 N1 124.3(2)
O2 C4 C3 127.4(2)
N1 C4 C3 108.3(2)
C6 C5 C9 99.9(2)
C6 C5 C2 106.2(2)
C9 C5 C2 99.3(2)
C7 C6 C5 107.9(2)
C6 C7 C8 107.8(2)
C7 C8 C9 100.7(2)
C7 C8 C3 106.1(2)
C9 C8 C3 99.38(19)
C5 C9 C8 94.0(2)
C23 C10 C11 122.0(2)
C23 C10 N1 119.7(2)
C11 C10 N1 118.3(2)
C12 C11 C10 119.9(2)
C11 C12 C13 120.8(2)
C14 C13 C12 122.1(2)
C14 C13 C22 119.1(2)
C12 C13 C22 118.7(2)
C13 C14 C15 121.5(2)
C14 C15 C20 119.6(2)
C14 C15 C16 121.6(2)
C20 C15 C16 118.8(2)
C17 C16 C15 120.0(3)
C16 C17 C18 120.9(3)
C19 C18 C17 121.0(3)
C18 C19 C20 120.3(3)
C21 C20 C19 121.9(2)
C21 C20 C15 119.0(2)
C19 C20 C15 119.1(2)
C22 C21 C20 121.5(2)
C21 C22 C23 122.2(2)
C21 C22 C13 119.2(2)
C23 C22 C13 118.6(2)
C10 C23 C22 119.9(2)
Cl2 C24 Cl3 111.62(16)
Cl2 C24 Cl1 110.36(17)
Cl3 C24 Cl1 109.62(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.205(3)
O2 C4 1.222(3)
N1 C4 1.380(3)
N1 C1 1.395(3)
N1 C10 1.439(3)
C1 C2 1.500(3)
C2 C3 1.541(3)
C2 C5 1.557(3)
C3 C4 1.503(4)
C3 C8 1.569(3)
C5 C6 1.510(4)
C5 C9 1.538(4)
C6 C7 1.329(4)
C7 C8 1.496(4)
C8 C9 1.539(4)
C10 C23 1.351(3)
C10 C11 1.411(3)
C11 C12 1.357(3)
C12 C13 1.426(3)
C13 C14 1.396(3)
C13 C22 1.433(3)
C14 C15 1.400(4)
C15 C20 1.424(4)
C15 C16 1.433(3)
C16 C17 1.364(4)
C17 C18 1.405(4)
C18 C19 1.360(4)
C19 C20 1.423(4)
C20 C21 1.404(3)
C21 C22 1.399(3)
C22 C23 1.430(3)
C24 Cl2 1.729(3)
C24 Cl3 1.737(3)
C24 Cl1 1.757(3)
