#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:09:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178423 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/44/4024436.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_4024436
loop_
_publ_author_name
'Kosuke Katagiri'
'Taichi Tohaya'
'Hyuma Masu'
'Masahide Tominaga'
'Isao Azumaya'
_publ_contact_author_address
'1314-1 Shido, Sanuki, Kagawa 769-2193, Japan'
_publ_contact_author_email       azumayai@kph.bunri-u.ac.jp
_publ_contact_author_name        'Isao Azumaya'
_publ_contact_author_phone       '+81 87 894 5111'
_publ_section_title
;
Effect of Aromatic-Aromatic Interactions on the Conformational
Stabilities of Macrocycle and Preorganized Structure during Macrocyclization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2804
_journal_page_last               2810
_journal_paper_doi               10.1021/jo802801n
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C50 H42 Cl6 N2 O2'
_chemical_formula_weight         915.56
_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                 111.575(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   30.709(5)
_cell_length_b                   8.4717(14)
_cell_length_c                   18.198(3)
_cell_measurement_reflns_used    1826
_cell_measurement_temperature    150
_cell_measurement_theta_max      21.60
_cell_measurement_theta_min      2.41
_cell_volume                     4402.6(13)
_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      150
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.956
_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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10371
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.60
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.434
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9183
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1896
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4405
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0638
_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)+(0.1000P)²+0.0591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.2015
_reflns_number_gt                2464
_reflns_number_total             4405
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802801n_si_003.cif
_cod_data_source_block           dianilide3
_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      C2/c
_cod_database_code               4024436
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl3 Cl 0.05813(7) 0.50724(19) 0.24923(9) 0.0736(5) Uani 0.747(2) 1 d P A 1
Cl2 Cl 0.13050(5) 0.68979(15) 0.36468(7) 0.0722(5) Uani 0.747(2) 1 d P A 1
Cl1 Cl 0.10242(8) 0.39128(17) 0.40841(9) 0.0936(8) Uani 0.747(2) 1 d P A 1
C3 C 0.04429(12) 0.4736(3) 0.55605(17) 0.0435(8) Uani 1 1 d . . .
H3 H 0.0747 0.4562 0.5944 0.052 Uiso 1 1 calc R . .
C9 C 0.10240(14) 0.0367(4) 0.48552(18) 0.0525(9) Uani 1 1 d . . .
H9 H 0.0915 -0.0137 0.4354 0.063 Uiso 1 1 calc R . .
O1 O -0.01867(9) 0.2065(2) 0.62927(13) 0.0584(7) Uani 1 1 d . . .
C4 C 0.03583(12) 0.6047(3) 0.50713(17) 0.0437(8) Uani 1 1 d . . .
H4 H 0.0605 0.6765 0.5121 0.052 Uiso 1 1 calc R . .
C2 C 0.00862(12) 0.3683(3) 0.54913(17) 0.0426(8) Uani 1 1 d . . .
N1 N 0.05505(11) 0.1583(3) 0.63740(15) 0.0599(9) Uani 1 1 d . . .
C10 C 0.14957(14) 0.0817(4) 0.51945(18) 0.0568(10) Uani 1 1 d . B .
C8 C 0.07147(14) 0.0639(4) 0.52329(18) 0.0531(9) Uani 1 1 d . . .
H8 H 0.0397 0.0325 0.4991 0.064 Uiso 1 1 calc R . .
C16 C 0.24277(13) -0.0234(4) 0.39777(18) 0.0545(9) Uani 1 1 d . . .
C7 C 0.08692(15) 0.1371(4) 0.59652(19) 0.0579(10) Uani 1 1 d . . .
C1 C 0.01355(14) 0.2354(4) 0.60686(17) 0.0516(9) Uani 1 1 d . . .
C19 C 0.27415(12) -0.0672(4) 0.35535(19) 0.0558(9) Uani 1 1 d . B .
C13 C 0.18243(13) 0.0508(4) 0.47810(18) 0.0580(10) Uani 1 1 d . . .
C15 C 0.19662(16) 0.0219(5) 0.3585(2) 0.0521(12) Uani 0.798(4) 1 d P B 1
H15 H 0.1850 0.0279 0.3025 0.063 Uiso 0.798(4) 1 calc PR B 1
C20 C 0.27121(13) 0.0072(5) 0.28642(19) 0.0661(11) Uani 1 1 d . . .
H20 H 0.2487 0.0881 0.2651 0.079 Uiso 1 1 calc R B .
C14 C 0.16691(15) 0.0585(5) 0.3967(2) 0.0513(11) Uani 0.798(4) 1 d P B 1
H14 H 0.1356 0.0891 0.3671 0.062 Uiso 0.798(4) 1 calc PR B 1
C12 C 0.13375(16) 0.1813(5) 0.63163(19) 0.0701(12) Uani 1 1 d . B .
H12 H 0.1446 0.2298 0.6822 0.084 Uiso 1 1 calc R . .
C11 C 0.16452(15) 0.1552(5) 0.59359(19) 0.0695(11) Uani 1 1 d . . .
H11 H 0.1962 0.1875 0.6179 0.083 Uiso 1 1 calc R B .
C5 C 0.06195(17) 0.0518(5) 0.7055(2) 0.0807(14) Uani 1 1 d . . .
H5A H 0.0477 0.1007 0.7408 0.097 Uiso 1 1 calc R . .
H5B H 0.0959 0.0400 0.7359 0.097 Uiso 1 1 calc R . .
C22 C 0.33347(14) -0.1508(5) 0.2779(2) 0.0737(12) Uani 1 1 d . . .
H22 H 0.3539 -0.1792 0.2515 0.088 Uiso 1 1 calc R B .
C6 C 0.0409(2) -0.1081(5) 0.6811(3) 0.1055(19) Uani 1 1 d . . .
H6A H 0.0068 -0.0985 0.6564 0.158 Uiso 1 1 calc R . .
H6B H 0.0490 -0.1763 0.7277 0.158 Uiso 1 1 calc R . .
H6C H 0.0532 -0.1542 0.6432 0.158 Uiso 1 1 calc R . .
C25 C 0.08447(17) 0.5500(5) 0.3532(3) 0.0795(13) Uani 1 1 d . . .
C21 C 0.30088(14) -0.0351(6) 0.2480(2) 0.0834(14) Uani 1 1 d . B .
H21 H 0.2985 0.0169 0.2005 0.100 Uiso 1 1 calc R . .
C23 C 0.33650(18) -0.2256(6) 0.3463(3) 0.0954(15) Uani 1 1 d . B .
H23 H 0.3591 -0.3066 0.3673 0.114 Uiso 1 1 calc R . .
C24 C 0.30737(16) -0.1845(6) 0.3843(3) 0.0938(15) Uani 1 1 d . . .
H24 H 0.3099 -0.2377 0.4317 0.113 Uiso 1 1 calc R B .
C18 C 0.2285(2) 0.0195(9) 0.5189(3) 0.112(3) Uani 0.798(4) 1 d P B 1
H18 H 0.2404 0.0247 0.5750 0.134 Uiso 0.798(4) 1 calc PR B 1
C17 C 0.2580(2) -0.0193(9) 0.4809(3) 0.114(3) Uani 0.798(4) 1 d P B 1
H17 H 0.2897 -0.0443 0.5114 0.136 Uiso 0.798(4) 1 calc PR B 1
Cl4 Cl 0.05437(15) 0.3425(4) 0.3707(2) 0.0575(13) Uani 0.253(2) 1 d P A 2
Cl5 Cl 0.14396(19) 0.4727(6) 0.4455(4) 0.126(3) Uani 0.253(2) 1 d P A 2
Cl6 Cl 0.0901(3) 0.5424(7) 0.2810(4) 0.104(2) Uani 0.253(2) 1 d P A 2
C26 C 0.1820(5) -0.1082(15) 0.4391(8) 0.041(4) Uani 0.202(4) 1 d P B 2
H26 H 0.1613 -0.1885 0.4428 0.050 Uiso 0.202(4) 1 calc PR B 2
C28 C 0.2448(5) 0.1128(15) 0.4274(8) 0.037(4) Uani 0.202(4) 1 d P B 2
H28 H 0.2649 0.1908 0.4195 0.045 Uiso 0.202(4) 1 calc PR B 2
C29 C 0.2169(5) 0.1483(16) 0.4723(8) 0.037(4) Uani 0.202(4) 1 d P B 2
H29 H 0.2224 0.2455 0.5002 0.045 Uiso 0.202(4) 1 calc PR B 2
C27 C 0.2111(5) -0.1374(18) 0.3987(8) 0.042(4) Uani 0.202(4) 1 d P B 2
H27 H 0.2094 -0.2346 0.3718 0.050 Uiso 0.202(4) 1 calc PR B 2
H25 H 0.0644(16) 0.612(6) 0.373(3) 0.117(17) Uiso 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C8 C9 C10 121.6(3) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C3 C4 C2 120.4(3) . 5_566 ?
C3 C4 H4 119.8 . . ?
C2 C4 H4 119.8 5_566 . ?
C3 C2 C4 119.4(3) . 5_566 ?
C3 C2 C1 123.0(3) . . ?
C4 C2 C1 117.1(3) 5_566 . ?
C1 N1 C7 124.2(3) . . ?
C1 N1 C5 117.3(3) . . ?
C7 N1 C5 116.1(3) . . ?
C11 C10 C9 117.7(3) . . ?
C11 C10 C13 121.5(4) . . ?
C9 C10 C13 120.8(3) . . ?
C9 C8 C7 119.9(4) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C28 C16 C27 124.1(9) . . ?
C28 C16 C15 81.3(7) . . ?
C27 C16 C15 66.9(7) . . ?
C28 C16 C17 64.9(7) . . ?
C27 C16 C17 87.8(7) . . ?
C15 C16 C17 114.8(4) . . ?
C28 C16 C19 120.6(7) . . ?
C27 C16 C19 115.3(7) . . ?
C15 C16 C19 122.5(3) . . ?
C17 C16 C19 122.7(4) . . ?
C8 C7 C12 119.5(3) . . ?
C8 C7 N1 119.6(4) . . ?
C12 C7 N1 120.8(3) . . ?
O1 C1 N1 121.3(3) . . ?
O1 C1 C2 119.6(3) . . ?
N1 C1 C2 118.9(3) . . ?
C20 C19 C24 117.9(3) . . ?
C20 C19 C16 121.4(3) . . ?
C24 C19 C16 120.7(3) . . ?
C18 C13 C29 58.9(6) . . ?
C18 C13 C14 118.3(4) . . ?
C29 C13 C14 82.0(6) . . ?
C18 C13 C10 121.4(3) . . ?
C29 C13 C10 128.2(7) . . ?
C14 C13 C10 120.3(3) . . ?
C18 C13 C26 84.9(7) . . ?
C29 C13 C26 111.7(9) . . ?
C14 C13 C26 66.5(5) . . ?
C10 C13 C26 120.1(6) . . ?
C14 C15 C16 123.1(4) . . ?
C14 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C19 C20 C21 120.5(4) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C11 C12 C7 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C12 C11 C10 120.8(4) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
N1 C5 C6 112.9(3) . . ?
N1 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
N1 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C21 C22 C23 119.3(4) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Cl6 C25 Cl1 114.1(4) . . ?
Cl6 C25 Cl2 76.9(4) . . ?
Cl1 C25 Cl2 113.2(3) . . ?
Cl6 C25 Cl3 32.8(4) . . ?
Cl1 C25 Cl3 113.4(2) . . ?
Cl2 C25 Cl3 106.5(2) . . ?
Cl6 C25 Cl4 108.9(4) . . ?
Cl1 C25 Cl4 43.89(17) . . ?
Cl2 C25 Cl4 157.1(3) . . ?
Cl3 C25 Cl4 86.4(2) . . ?
Cl6 C25 Cl5 111.8(5) . . ?
Cl1 C25 Cl5 41.7(2) . . ?
Cl2 C25 Cl5 72.2(2) . . ?
Cl3 C25 Cl5 134.9(3) . . ?
Cl4 C25 Cl5 85.3(3) . . ?
Cl6 C25 H25 134(3) . . ?
Cl1 C25 H25 109(3) . . ?
Cl2 C25 H25 101(3) . . ?
Cl3 C25 H25 113(3) . . ?
Cl4 C25 H25 91(3) . . ?
Cl5 C25 H25 111(3) . . ?
C22 C21 C20 120.6(4) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C24 C23 C22 120.4(4) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C19 121.4(4) . . ?
C23 C24 H24 119.3 . . ?
C19 C24 H24 119.3 . . ?
C13 C18 C17 121.3(4) . . ?
C13 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C17 C16 122.0(5) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C27 C26 C13 120.9(11) . . ?
C27 C26 H26 119.5 . . ?
C13 C26 H26 119.5 . . ?
C16 C28 C29 119.5(12) . . ?
C16 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C13 C29 C28 124.3(12) . . ?
C13 C29 H29 117.9 . . ?
C28 C29 H29 117.9 . . ?
C26 C27 C16 118.9(12) . . ?
C26 C27 H27 120.6 . . ?
C16 C27 H27 120.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl3 C25 1.801(5) . ?
Cl2 C25 1.796(5) . ?
Cl1 C25 1.648(5) . ?
C3 C2 1.382(4) . ?
C3 C4 1.387(4) . ?
C3 H3 0.9500 . ?
C9 C8 1.381(5) . ?
C9 C10 1.403(5) . ?
C9 H9 0.9500 . ?
O1 C1 1.225(4) . ?
C4 C2 1.392(4) 5_566 ?
C4 H4 0.9500 . ?
C2 C4 1.392(4) 5_566 ?
C2 C1 1.509(4) . ?
N1 C1 1.356(4) . ?
N1 C7 1.442(4) . ?
N1 C5 1.484(4) . ?
C10 C11 1.401(5) . ?
C10 C13 1.487(5) . ?
C8 C7 1.386(4) . ?
C8 H8 0.9500 . ?
C16 C28 1.265(13) . ?
C16 C27 1.374(15) . ?
C16 C15 1.386(6) . ?
C16 C17 1.410(5) . ?
C16 C19 1.486(5) . ?
C7 C12 1.393(5) . ?
C19 C20 1.377(5) . ?
C19 C24 1.382(5) . ?
C13 C18 1.360(6) . ?
C13 C29 1.378(13) . ?
C13 C14 1.381(5) . ?
C13 C26 1.521(14) . ?
C15 C14 1.370(6) . ?
C15 H15 0.9500 . ?
C20 C21 1.384(5) . ?
C20 H20 0.9500 . ?
C14 H14 0.9500 . ?
C12 C11 1.379(5) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C5 C6 1.496(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C22 C21 1.362(6) . ?
C22 C23 1.369(6) . ?
C22 H22 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C25 Cl6 1.389(6) . ?
C25 Cl4 2.065(6) . ?
C25 Cl5 2.081(7) . ?
C25 H25 0.97(5) . ?
C21 H21 0.9500 . ?
C23 C24 1.362(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C18 C17 1.367(7) . ?
C18 H18 0.9500 . ?
C17 H17 0.9500 . ?
C26 C27 1.37(2) . ?
C26 H26 0.9500 . ?
C28 C29 1.42(2) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C27 H27 0.9500 . ?
