#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:32:22 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178395 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/17/4021724.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_4021724
loop_
_publ_author_name
'Zhi-Guo Wang'
'Bao-Han Zhou'
'Yun-Feng Chen'
'Guo-Dong Yin'
'Yi-Tao Li'
'An-Xin Wu'
'Lyle Isaacs'
_publ_section_title
;
 Substituent Effects Control the Self-Association of Molecular Clips
 in the Crystalline State
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4502
_journal_page_last               4508
_journal_paper_doi               10.1021/jo0603375
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C26 H26 N4 O6'
_chemical_formula_sum            'C26 H26 N4 O6'
_chemical_formula_weight         490.51
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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                 108.106(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.698(3)
_cell_length_b                   9.7251(16)
_cell_length_c                   16.164(3)
_cell_measurement_reflns_used    2102
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      26.51
_cell_measurement_theta_min      2.50
_cell_volume                     2345.6(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      292(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6721
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2551
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0596P)²+1.0618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1204
_reflns_number_gt                2077
_reflns_number_total             2551
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0603375si20060217_102404.cif
_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      'C 2/c'
_cod_database_code               4021724
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
C1 C 0.74836(11) 0.95646(17) 0.14824(11) 0.0412(4) Uani 1 1 d .
H1 H 0.7214 0.9593 0.1919 0.049 Uiso 1 1 calc R
C2 C 0.73496(12) 1.06456(17) 0.08924(12) 0.0455(4) Uani 1 1 d .
H2 H 0.6988 1.1384 0.0932 0.055 Uiso 1 1 calc R
C3 C 0.77532(12) 1.06188(16) 0.02498(12) 0.0430(4) Uani 1 1 d .
H3 H 0.7658 1.1331 -0.0152 0.052 Uiso 1 1 calc R
C4 C 0.83020(11) 0.95270(16) 0.02044(10) 0.0370(4) Uani 1 1 d .
H4 H 0.8587 0.9527 -0.0221 0.044 Uiso 1 1 calc R
C5 C 0.84351(10) 0.84323(15) 0.07816(10) 0.0320(3) Uani 1 1 d .
C6 C 0.80137(10) 0.84425(16) 0.14304(10) 0.0333(3) Uani 1 1 d .
C7 C 0.80568(10) 0.72436(17) 0.20395(10) 0.0360(4) Uani 1 1 d .
H7A H 0.7742 0.7504 0.2446 0.043 Uiso 1 1 calc R
H7B H 0.7733 0.6480 0.1698 0.043 Uiso 1 1 calc R
C8 C 0.94227(10) 0.73360(15) 0.33306(10) 0.0311(3) Uani 1 1 d .
C9 C 1.04688(9) 0.60746(15) 0.28648(9) 0.0289(3) Uani 1 1 d .
C10 C 1.08179(10) 0.46303(16) 0.32052(10) 0.0324(3) Uani 1 1 d .
C11 C 1.04157(14) 0.2636(2) 0.38668(14) 0.0572(5) Uani 1 1 d .
H11A H 1.0610 0.2660 0.4498 0.069 Uiso 1 1 calc R
H11B H 1.0890 0.2230 0.3681 0.069 Uiso 1 1 calc R
C12 C 0.95841(17) 0.1805(2) 0.35394(15) 0.0646(6) Uani 1 1 d .
H12A H 0.9099 0.2272 0.3664 0.097 Uiso 1 1 calc R
H12B H 0.9674 0.0923 0.3821 0.097 Uiso 1 1 calc R
H12C H 0.9442 0.1681 0.2922 0.097 Uiso 1 1 calc R
C13 C 1.09931(11) 0.72402(17) 0.43323(10) 0.0355(4) Uani 1 1 d .
H13A H 1.1376 0.6448 0.4536 0.043 Uiso 1 1 calc R
H13B H 1.0723 0.7476 0.4778 0.043 Uiso 1 1 calc R
N1 N 0.89502(8) 0.67553(13) 0.25426(8) 0.0314(3) Uani 1 1 d .
N2 N 1.02877(8) 0.68649(13) 0.35436(8) 0.0322(3) Uani 1 1 d .
O1 O 0.91227(8) 0.80837(12) 0.37726(7) 0.0429(3) Uani 1 1 d .
O2 O 1.15109(8) 0.41534(12) 0.31837(8) 0.0461(3) Uani 1 1 d .
O3 O 1.02261(8) 0.40331(12) 0.35183(8) 0.0465(3) 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'
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
C6 C1 C2 121.17(16) . .
C6 C1 H1 119.4 . .
C2 C1 H1 119.4 . .
C3 C2 C1 119.78(15) . .
C3 C2 H2 120.1 . .
C1 C2 H2 120.1 . .
C2 C3 C4 119.70(16) . .
C2 C3 H3 120.2 . .
C4 C3 H3 120.2 . .
C3 C4 C5 121.27(16) . .
C3 C4 H4 119.4 . .
C5 C4 H4 119.4 . .
C4 C5 C6 119.31(14) . .
C4 C5 C13 118.52(14) . 2_755
C6 C5 C13 122.14(13) . 2_755
C1 C6 C5 118.73(15) . .
C1 C6 C7 118.14(14) . .
C5 C6 C7 122.99(14) . .
N1 C7 C6 116.90(13) . .
N1 C7 H7A 108.1 . .
C6 C7 H7A 108.1 . .
N1 C7 H7B 108.1 . .
C6 C7 H7B 108.1 . .
H7A C7 H7B 107.3 . .
O1 C8 N2 126.01(14) . .
O1 C8 N1 126.41(14) . .
N2 C8 N1 107.52(13) . .
N2 C9 N1 113.97(12) . 2_755
N2 C9 C10 110.26(12) . .
N1 C9 C10 112.05(12) 2_755 .
N2 C9 C9 102.18(12) . 2_755
N1 C9 C9 103.58(12) 2_755 2_755
C10 C9 C9 114.35(7) . 2_755
O2 C10 O3 126.57(15) . .
O2 C10 C9 124.65(14) . .
O3 C10 C9 108.78(12) . .
O3 C11 C12 108.46(16) . .
O3 C11 H11A 110.0 . .
C12 C11 H11A 110.0 . .
O3 C11 H11B 110.0 . .
C12 C11 H11B 110.0 . .
H11A C11 H11B 108.4 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N2 C13 C5 113.92(12) . 2_755
N2 C13 H13A 108.8 . .
C5 C13 H13A 108.8 2_755 .
N2 C13 H13B 108.8 . .
C5 C13 H13B 108.8 2_755 .
H13A C13 H13B 107.7 . .
C8 N1 C9 112.01(12) . 2_755
C8 N1 C7 121.81(13) . .
C9 N1 C7 121.87(12) 2_755 .
C8 N2 C9 113.70(12) . .
C8 N2 C13 124.18(13) . .
C9 N2 C13 121.78(12) . .
C10 O3 C11 118.13(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.391(2) .
C1 C2 1.391(2) .
C1 H1 0.9300 .
C2 C3 1.375(3) .
C2 H2 0.9300 .
C3 C4 1.384(2) .
C3 H3 0.9300 .
C4 C5 1.388(2) .
C4 H4 0.9300 .
C5 C6 1.403(2) .
C5 C13 1.512(2) 2_755
C6 C7 1.514(2) .
C7 N1 1.4646(19) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 O1 1.2125(18) .
C8 N2 1.372(2) .
C8 N1 1.3800(19) .
C9 N2 1.4385(18) .
C9 N1 1.4413(18) 2_755
C9 C10 1.545(2) .
C9 C9 1.574(3) 2_755
C10 O2 1.1931(19) .
C10 O3 1.3224(19) .
C11 O3 1.465(2) .
C11 C12 1.486(3) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 N2 1.4516(19) .
C13 C5 1.512(2) 2_755
C13 H13A 0.9700 .
C13 H13B 0.9700 .
N1 C9 1.4412(18) 2_755
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7B O2 0.97 2.53 3.126(2) 119.3 2_755
C2 H2 O1 0.93 2.55 3.469(2) 168.5 4_655
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
C6 C1 C2 C3 -0.7(3) . .
C1 C2 C3 C4 -1.1(3) . .
C2 C3 C4 C5 1.8(2) . .
C3 C4 C5 C6 -0.8(2) . .
C3 C4 C5 C13 177.04(15) . 2_755
C2 C1 C6 C5 1.7(2) . .
C2 C1 C6 C7 -174.22(15) . .
C4 C5 C6 C1 -0.9(2) . .
C13 C5 C6 C1 -178.70(15) 2_755 .
C4 C5 C6 C7 174.75(14) . .
C13 C5 C6 C7 -3.0(2) 2_755 .
C1 C6 C7 N1 -129.04(16) . .
C5 C6 C7 N1 55.3(2) . .
N2 C9 C10 O2 -123.96(16) . .
N1 C9 C10 O2 4.1(2) 2_755 .
C9 C9 C10 O2 121.58(18) 2_755 .
N2 C9 C10 O3 55.93(15) . .
N1 C9 C10 O3 -175.99(12) 2_755 .
C9 C9 C10 O3 -58.52(19) 2_755 .
O1 C8 N1 C9 172.14(14) . 2_755
N2 C8 N1 C9 -10.50(16) . 2_755
O1 C8 N1 C7 15.1(2) . .
N2 C8 N1 C7 -167.56(12) . .
C6 C7 N1 C8 86.16(17) . .
C6 C7 N1 C9 -68.66(19) . 2_755
O1 C8 N2 C9 -175.68(14) . .
N1 C8 N2 C9 6.94(17) . .
O1 C8 N2 C13 -2.3(2) . .
N1 C8 N2 C13 -179.71(13) . .
N1 C9 N2 C8 110.01(14) 2_755 .
C10 C9 N2 C8 -122.97(13) . .
C9 C9 N2 C8 -1.02(14) 2_755 .
N1 C9 N2 C13 -63.52(17) 2_755 .
C10 C9 N2 C13 63.50(17) . .
C9 C9 N2 C13 -174.55(12) 2_755 .
C5 C13 N2 C8 -94.88(17) 2_755 .
C5 C13 N2 C9 77.96(18) 2_755 .
O2 C10 O3 C11 -1.0(3) . .
C9 C10 O3 C11 179.12(14) . .
C12 C11 O3 C10 -135.55(17) . .
