#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:09:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178423 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/44/4024437.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_4024437
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            'C60 H52 N4 O4'
_chemical_formula_weight         893.06
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 101.834(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.765(2)
_cell_length_b                   24.472(7)
_cell_length_c                   13.084(4)
_cell_measurement_reflns_used    910
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.47
_cell_measurement_theta_min      2.30
_cell_volume                     2433.5(12)
_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 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker Smart1000 CCD'
_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  0.0980
_diffrn_reflns_av_sigmaI/netI    0.1874
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14448
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.9849
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.878
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.946
_refine_ls_R_factor_all          0.2078
_refine_ls_R_factor_gt           0.0874
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1424P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2175
_refine_ls_wR_factor_ref         0.2942
_reflns_number_gt                2172
_reflns_number_total             5493
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802801n_si_004.cif
_cod_data_source_block           macrocycle5
_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      P2(1)/n
_cod_database_code               4024437
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O1 O -0.0538(4) 0.10907(11) 0.0552(2) 0.0491(8) Uani 1 1 d . . .
N2 N 0.5836(5) 0.27413(12) 0.2029(3) 0.0413(9) Uani 1 1 d . . .
N1 N 0.0782(4) 0.03324(13) 0.1315(2) 0.0390(9) Uani 1 1 d . . .
O2 O 0.2942(4) 0.28283(12) 0.1286(2) 0.0535(9) Uani 1 1 d . . .
C23 C 1.5200(5) 0.05056(17) 0.6594(3) 0.0388(10) Uani 1 1 d . . .
C27 C 1.6794(5) -0.03249(17) 0.7134(3) 0.0400(10) Uani 1 1 d . . .
H27 H 1.7017 -0.0697 0.7003 0.048 Uiso 1 1 calc R . .
C20 C 1.3857(6) 0.08251(17) 0.5846(3) 0.0432(11) Uani 1 1 d . . .
C19 C 1.4193(6) 0.13542(17) 0.5570(3) 0.0436(11) Uani 1 1 d . . .
H19 H 1.5318 0.1510 0.5830 0.052 Uiso 1 1 calc R . .
C5 C 0.5535(5) 0.17051(17) 0.0774(3) 0.0412(10) Uani 1 1 d . . .
H5 H 0.6562 0.1905 0.0721 0.049 Uiso 1 1 calc R . .
C12 C 0.8938(6) 0.24745(17) 0.2569(3) 0.0425(11) Uani 1 1 d . . .
H12 H 0.9242 0.2738 0.2103 0.051 Uiso 1 1 calc R . .
C4 C 0.4199(5) 0.19571(16) 0.1165(3) 0.0380(10) Uani 1 1 d . . .
C2 C 0.2542(5) 0.11152(16) 0.0939(3) 0.0340(9) Uani 1 1 d . . .
C28 C 1.5493(5) -0.00436(16) 0.6457(3) 0.0403(10) Uani 1 1 d . . .
H28 H 1.4785 -0.0232 0.5887 0.048 Uiso 1 1 calc R . .
C11 C 0.7188(6) 0.24012(16) 0.2616(3) 0.0394(10) Uani 1 1 d . . .
C18 C 1.2918(6) 0.16597(18) 0.4923(3) 0.0454(11) Uani 1 1 d . . .
H18 H 1.3182 0.2023 0.4747 0.054 Uiso 1 1 calc R . .
C13 C 1.0237(6) 0.21732(16) 0.3184(3) 0.0412(10) Uani 1 1 d . . .
H13 H 1.1428 0.2240 0.3147 0.049 Uiso 1 1 calc R . .
C1 C 0.0825(6) 0.08462(17) 0.0940(3) 0.0389(10) Uani 1 1 d . . .
C24 C 1.6192(6) 0.07604(17) 0.7468(3) 0.0441(11) Uani 1 1 d . . .
H24 H 1.5994 0.1136 0.7584 0.053 Uiso 1 1 calc R . .
C15 C 0.8096(6) 0.17024(17) 0.3911(3) 0.0425(10) Uani 1 1 d . . .
H15 H 0.7794 0.1433 0.4367 0.051 Uiso 1 1 calc R . .
C25 C 1.7459(6) 0.04826(17) 0.8176(3) 0.0457(11) Uani 1 1 d . . .
H25 H 1.8107 0.0664 0.8774 0.055 Uiso 1 1 calc R . .
C14 C 0.9862(5) 0.17738(16) 0.3858(3) 0.0401(10) Uani 1 1 d . . .
C21 C 1.2207(6) 0.05997(18) 0.5425(3) 0.0452(11) Uani 1 1 d . . .
H21 H 1.1964 0.0232 0.5583 0.054 Uiso 1 1 calc R . .
C6 C 0.5372(6) 0.11649(17) 0.0463(3) 0.0424(10) Uani 1 1 d . . .
H6 H 0.6263 0.0997 0.0171 0.051 Uiso 1 1 calc R . .
C8 C 0.4270(6) 0.25369(17) 0.1505(3) 0.0428(11) Uani 1 1 d . . .
C22 C 1.0930(6) 0.09045(17) 0.4783(3) 0.0445(11) Uani 1 1 d . . .
H22 H 0.9814 0.0745 0.4513 0.053 Uiso 1 1 calc R . .
C3 C 0.2691(5) 0.16614(17) 0.1210(3) 0.0388(10) Uani 1 1 d . . .
H3 H 0.1741 0.1838 0.1432 0.047 Uiso 1 1 calc R . .
C17 C 1.1248(6) 0.14437(16) 0.4522(3) 0.0396(10) Uani 1 1 d . . .
C16 C 0.6779(6) 0.20156(17) 0.3314(3) 0.0447(11) Uani 1 1 d . . .
H16 H 0.5593 0.1968 0.3381 0.054 Uiso 1 1 calc R . .
C7 C 0.3902(5) 0.08681(16) 0.0580(3) 0.0408(10) Uani 1 1 d . . .
H7 H 0.3830 0.0490 0.0411 0.049 Uiso 1 1 calc R . .
C29 C -0.0962(6) 0.00774(18) 0.1239(3) 0.0477(11) Uani 1 1 d . . .
H29A H -0.0851 -0.0323 0.1164 0.057 Uiso 1 1 calc R . .
H29B H -0.1770 0.0215 0.0606 0.057 Uiso 1 1 calc R . .
C9 C 0.5965(7) 0.33190(17) 0.2296(4) 0.0558(13) Uani 1 1 d . . .
H9A H 0.5088 0.3527 0.1787 0.067 Uiso 1 1 calc R . .
H9B H 0.7150 0.3455 0.2257 0.067 Uiso 1 1 calc R . .
C10 C 0.5646(10) 0.3409(2) 0.3372(4) 0.100(2) Uani 1 1 d . . .
H10A H 0.4469 0.3277 0.3409 0.151 Uiso 1 1 calc R . .
H10B H 0.5731 0.3800 0.3536 0.151 Uiso 1 1 calc R . .
H10C H 0.6530 0.3209 0.3877 0.151 Uiso 1 1 calc R . .
C30 C -0.1741(7) 0.0195(2) 0.2181(4) 0.0769(17) Uani 1 1 d . . .
H30A H -0.0969 0.0047 0.2807 0.115 Uiso 1 1 calc R . .
H30B H -0.2904 0.0024 0.2091 0.115 Uiso 1 1 calc R . .
H30C H -0.1856 0.0591 0.2259 0.115 Uiso 1 1 calc R . .
C26 C 1.7774(5) -0.00645(17) 0.8000(3) 0.0391(10) 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
_geom_angle_publ_flag
C8 N2 C11 122.4(3) . . ?
C8 N2 C9 119.2(4) . . ?
C11 N2 C9 115.4(3) . . ?
C1 N1 C26 125.0(3) . 3_756 ?
C1 N1 C29 117.3(3) . . ?
C26 N1 C29 115.9(3) 3_756 . ?
C28 C23 C24 117.7(4) . . ?
C28 C23 C20 122.3(4) . . ?
C24 C23 C20 119.9(4) . . ?
C28 C27 C26 120.1(4) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C19 C20 C21 118.2(4) . . ?
C19 C20 C23 121.1(4) . . ?
C21 C20 C23 120.7(4) . . ?
C18 C19 C20 121.1(4) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C6 C5 C4 120.1(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C13 C12 C11 121.0(4) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C3 C4 C5 118.9(4) . . ?
C3 C4 C8 117.7(4) . . ?
C5 C4 C8 123.3(4) . . ?
C7 C2 C3 118.8(4) . . ?
C7 C2 C1 123.7(4) . . ?
C3 C2 C1 117.1(4) . . ?
C23 C28 C27 121.3(4) . . ?
C23 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C12 C11 C16 118.3(4) . . ?
C12 C11 N2 121.2(4) . . ?
C16 C11 N2 120.3(4) . . ?
C19 C18 C17 121.1(4) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C12 C13 C14 121.9(4) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
O1 C1 N1 121.2(4) . . ?
O1 C1 C2 118.6(4) . . ?
N1 C1 C2 120.0(4) . . ?
C25 C24 C23 121.9(4) . . ?
C25 C24 H24 119.0 . . ?
C23 C24 H24 119.0 . . ?
C16 C15 C14 121.4(4) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C24 C25 C26 119.2(4) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C13 C14 C15 117.1(4) . . ?
C13 C14 C17 122.5(4) . . ?
C15 C14 C17 120.4(4) . . ?
C22 C21 C20 120.8(4) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C5 C6 C7 119.7(4) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
O2 C8 N2 121.3(4) . . ?
O2 C8 C4 120.2(4) . . ?
N2 C8 C4 118.4(4) . . ?
C21 C22 C17 121.2(4) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?
C2 C3 C4 121.4(4) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C22 C17 C18 117.5(4) . . ?
C22 C17 C14 121.1(4) . . ?
C18 C17 C14 121.4(4) . . ?
C15 C16 C11 120.2(4) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C2 C7 C6 120.8(4) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N1 C29 C30 112.3(4) . . ?
N1 C29 H29A 109.1 . . ?
C30 C29 H29A 109.1 . . ?
N1 C29 H29B 109.1 . . ?
C30 C29 H29B 109.1 . . ?
H29A C29 H29B 107.9 . . ?
N2 C9 C10 110.7(4) . . ?
N2 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C27 C26 C25 119.6(4) . . ?
C27 C26 N1 121.7(4) . 3_756 ?
C25 C26 N1 118.5(4) . 3_756 ?
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
O1 C1 1.231(5) . ?
N2 C8 1.362(5) . ?
N2 C11 1.433(5) . ?
N2 C9 1.455(5) . ?
N1 C1 1.353(5) . ?
N1 C26 1.441(5) 3_756 ?
N1 C29 1.475(5) . ?
O2 C8 1.238(5) . ?
C23 C28 1.381(5) . ?
C23 C24 1.389(5) . ?
C23 C20 1.496(5) . ?
C27 C28 1.382(5) . ?
C27 C26 1.385(5) . ?
C27 H27 0.9500 . ?
C20 C19 1.383(6) . ?
C20 C21 1.400(6) . ?
C19 C18 1.383(6) . ?
C19 H19 0.9500 . ?
C5 C6 1.381(5) . ?
C5 C4 1.392(5) . ?
C5 H5 0.9500 . ?
C12 C13 1.369(6) . ?
C12 C11 1.385(6) . ?
C12 H12 0.9500 . ?
C4 C3 1.388(5) . ?
C4 C8 1.484(6) . ?
C2 C7 1.380(5) . ?
C2 C3 1.382(5) . ?
C2 C1 1.487(5) . ?
C28 H28 0.9500 . ?
C11 C16 1.395(6) . ?
C18 C17 1.399(6) . ?
C18 H18 0.9500 . ?
C13 C14 1.387(5) . ?
C13 H13 0.9500 . ?
C24 C25 1.383(6) . ?
C24 H24 0.9500 . ?
C15 C16 1.384(6) . ?
C15 C14 1.398(5) . ?
C15 H15 0.9500 . ?
C25 C26 1.388(5) . ?
C25 H25 0.9500 . ?
C14 C17 1.477(6) . ?
C21 C22 1.380(5) . ?
C21 H21 0.9500 . ?
C6 C7 1.388(6) . ?
C6 H6 0.9500 . ?
C22 C17 1.398(5) . ?
C22 H22 0.9500 . ?
C3 H3 0.9500 . ?
C16 H16 0.9500 . ?
C7 H7 0.9500 . ?
C29 C30 1.509(6) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C9 C10 1.495(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C26 N1 1.441(5) 3_756 ?
