#------------------------------------------------------------------------------
#$Date: 2019-11-25 11:38:42 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/02/4130293.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_4130293
loop_
_publ_author_name
'Suzuki, Mitsuharu'
'Kotyk, Juliet F Khosrowabadi'
'Khan, Saeed I.'
'Rubin, Yves'
_publ_section_title
;
 Directing the Crystallization of Dehydro[24]annulenes into Supramolecular
 Nanotubular Scaffolds.
;
_journal_issue                   18
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5939
_journal_page_last               5956
_journal_paper_doi               10.1021/jacs.6b01939
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C28 H16 O4, C14 H14 N4 O2'
_chemical_formula_sum            'C42 H30 N4 O6'
_chemical_formula_weight         686.70
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                88.821(4)
_cell_angle_beta                 89.682(5)
_cell_angle_gamma                85.649(4)
_cell_formula_units_Z            1
_cell_length_a                   8.896(3)
_cell_length_b                   9.089(3)
_cell_length_c                   10.731(4)
_cell_measurement_reflns_used    5702
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.80
_cell_measurement_theta_min      3.80
_cell_volume                     865.0(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11171
_diffrn_reflns_theta_full        27.25
_diffrn_reflns_theta_max         28.82
_diffrn_reflns_theta_min         3.80
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_correction_T_min  0.9350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Bruker)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             358
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0381
_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)+(0.0505P)²+0.2964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1019
_reflns_number_gt                3863
_reflns_number_total             4377
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b01939_si_002.cif
_cod_data_source_block           1a-2a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4130293
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.02612(9) 0.63492(9) 0.22806(8) 0.02573(18) Uani 1 1 d .
H1 H 0.0654 0.6656 0.2926 0.039 Uiso 1 1 calc R
O2 O 0.34989(10) 0.63822(10) 0.90262(8) 0.0322(2) Uani 1 1 d .
H2 H 0.2883 0.7089 0.9217 0.048 Uiso 1 1 calc R
C1 C 0.41103(12) -0.08856(11) 0.14518(9) 0.0196(2) Uani 1 1 d .
C2 C 0.33966(12) 0.04959(11) 0.13350(9) 0.0201(2) Uani 1 1 d .
C3 C 0.27769(12) 0.17124(11) 0.11741(10) 0.0202(2) Uani 1 1 d .
C4 C 0.20790(12) 0.31432(11) 0.09458(9) 0.0192(2) Uani 1 1 d .
H4 H 0.1610 0.3349 0.0162 0.023 Uiso 1 1 calc R
C5 C 0.20468(11) 0.42342(11) 0.17889(9) 0.0180(2) Uani 1 1 d .
C6 C 0.26669(12) 0.39931(11) 0.29975(10) 0.0200(2) Uani 1 1 d .
C7 C 0.31195(12) 0.38780(11) 0.40554(10) 0.0218(2) Uani 1 1 d .
C8 C 0.34989(12) 0.38468(12) 0.52882(10) 0.0218(2) Uani 1 1 d .
C9 C 0.37526(12) 0.39008(11) 0.63902(10) 0.0211(2) Uani 1 1 d .
C10 C 0.38741(12) 0.43588(11) 0.76424(9) 0.0190(2) Uani 1 1 d .
C11 C 0.45484(11) 0.35479(11) 0.85784(9) 0.0191(2) Uani 1 1 d .
H11 H 0.4554 0.3986 0.9374 0.023 Uiso 1 1 calc R
C12 C 0.52476(11) 0.21052(11) 0.84813(9) 0.0191(2) Uani 1 1 d .
C13 C 0.14141(12) 0.57826(11) 0.14586(10) 0.0201(2) Uani 1 1 d .
H13A H 0.2246 0.6447 0.1458 0.024 Uiso 1 1 calc R
H13B H 0.1003 0.5792 0.0603 0.024 Uiso 1 1 calc R
C14 C 0.31655(13) 0.59000(12) 0.78303(10) 0.0248(2) Uani 1 1 d .
H14A H 0.3554 0.6579 0.7193 0.030 Uiso 1 1 calc R
H14B H 0.2059 0.5909 0.7730 0.030 Uiso 1 1 calc R
O3 O 0.12416(9) 0.84648(8) 0.96885(7) 0.02195(17) Uani 1 1 d .
N1 N 0.12860(12) 0.77071(11) 0.44564(9) 0.0282(2) Uani 1 1 d .
N2 N 0.08036(10) 1.06099(9) 0.85648(8) 0.01937(18) Uani 1 1 d .
H2A H 0.0184 1.1405 0.8463 0.023 Uiso 1 1 calc R
C15 C 0.28208(13) 0.92095(14) 0.56542(11) 0.0284(2) Uani 1 1 d .
H15 H 0.3748 0.9652 0.5732 0.034 Uiso 1 1 calc R
C16 C 0.25641(14) 0.83590(15) 0.46334(11) 0.0312(3) Uani 1 1 d .
H16 H 0.3339 0.8231 0.4024 0.037 Uiso 1 1 calc R
C17 C 0.02289(14) 0.79051(13) 0.53377(11) 0.0274(2) Uani 1 1 d .
H17 H -0.0688 0.7450 0.5234 0.033 Uiso 1 1 calc R
C18 C 0.03848(13) 0.87362(12) 0.63998(10) 0.0227(2) Uani 1 1 d .
H18 H -0.0405 0.8837 0.6998 0.027 Uiso 1 1 calc R
C19 C 0.17068(12) 0.94121(11) 0.65691(9) 0.0196(2) Uani 1 1 d .
C20 C 0.20289(12) 1.03329(12) 0.76820(10) 0.0221(2) Uani 1 1 d .
H20A H 0.2897 0.9835 0.8136 0.026 Uiso 1 1 calc R
H20B H 0.2341 1.1297 0.7370 0.026 Uiso 1 1 calc R
C21 C 0.05878(11) 0.96967(11) 0.95255(9) 0.0178(2) 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'
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'
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
C13 O1 H1 109.5 . .
C14 O2 H2 109.5 . .
C12 C1 C2 178.10(11) 2_656 .
C3 C2 C1 177.01(11) . .
C2 C3 C4 177.99(11) . .
C5 C4 C3 123.30(9) . .
C5 C4 H4 118.4 . .
C3 C4 H4 118.4 . .
C4 C5 C6 121.61(9) . .
C4 C5 C13 121.24(9) . .
C6 C5 C13 117.09(9) . .
C7 C6 C5 174.93(11) . .
C6 C7 C8 173.77(12) . .
C9 C8 C7 175.22(12) . .
C8 C9 C10 164.53(11) . .
C11 C10 C9 125.49(10) . .
C11 C10 C14 122.23(9) . .
C9 C10 C14 112.27(8) . .
C10 C11 C12 125.88(10) . .
C10 C11 H11 117.1 . .
C12 C11 H11 117.1 . .
C1 C12 C11 172.08(11) 2_656 .
O1 C13 C5 114.13(9) . .
O1 C13 H13A 108.7 . .
C5 C13 H13A 108.7 . .
O1 C13 H13B 108.7 . .
C5 C13 H13B 108.7 . .
H13A C13 H13B 107.6 . .
O2 C14 C10 110.17(8) . .
O2 C14 H14A 109.6 . .
C10 C14 H14A 109.6 . .
O2 C14 H14B 109.6 . .
C10 C14 H14B 109.6 . .
H14A C14 H14B 108.1 . .
C17 N1 C16 116.35(10) . .
C21 N2 C20 121.98(9) . .
C21 N2 H2A 119.0 . .
C20 N2 H2A 119.0 . .
C16 C15 C19 119.52(11) . .
C16 C15 H15 120.2 . .
C19 C15 H15 120.2 . .
N1 C16 C15 123.68(11) . .
N1 C16 H16 118.2 . .
C15 C16 H16 118.2 . .
N1 C17 C18 124.17(11) . .
N1 C17 H17 117.9 . .
C18 C17 H17 117.9 . .
C19 C18 C17 118.97(10) . .
C19 C18 H18 120.5 . .
C17 C18 H18 120.5 . .
C18 C19 C15 117.31(10) . .
C18 C19 C20 124.43(9) . .
C15 C19 C20 118.26(10) . .
N2 C20 C19 116.59(9) . .
N2 C20 H20A 108.1 . .
C19 C20 H20A 108.1 . .
N2 C20 H20B 108.1 . .
C19 C20 H20B 108.1 . .
H20A C20 H20B 107.3 . .
O3 C21 N2 125.55(10) . .
O3 C21 C21 120.27(11) . 2_577
N2 C21 C21 114.18(11) . 2_577
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C13 1.4225(13) .
O1 H1 0.8400 .
O2 C14 1.4050(14) .
O2 H2 0.8400 .
C1 C12 1.2088(15) 2_656
C1 C2 1.3671(14) .
C2 C3 1.2071(15) .
C3 C4 1.4151(14) .
C4 C5 1.3547(14) .
C4 H4 0.9500 .
C5 C6 1.4186(14) .
C5 C13 1.5114(14) .
C6 C7 1.2066(15) .
C7 C8 1.3664(15) .
C8 C9 1.2079(15) .
C9 C10 1.4221(15) .
C10 C11 1.3495(14) .
C10 C14 1.5088(14) .
C11 C12 1.4137(14) .
C11 H11 0.9500 .
C12 C1 1.2089(15) 2_656
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
O3 C21 1.2316(12) .
N1 C17 1.3351(16) .
N1 C16 1.3376(18) .
N2 C21 1.3324(13) .
N2 C20 1.4511(14) .
N2 H2A 0.8800 .
C15 C16 1.3836(17) .
C15 C19 1.3961(15) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 C18 1.3936(16) .
C17 H17 0.9500 .
C18 C19 1.3820(16) .
C18 H18 0.9500 .
C19 C20 1.5133(15) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C21 1.536(2) 2_577
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_4
C3 C4 C5 C6 -2.71(17) .
C3 C4 C5 C13 174.30(10) .
C8 C9 C10 C11 -175.7(4) .
C8 C9 C10 C14 3.7(5) .
C9 C10 C11 C12 -0.14(18) .
C14 C10 C11 C12 -179.48(10) .
C4 C5 C13 O1 125.52(11) .
C6 C5 C13 O1 -57.34(13) .
C11 C10 C14 O2 7.81(15) .
C9 C10 C14 O2 -171.61(10) .
C17 N1 C16 C15 -0.45(18) .
C19 C15 C16 N1 0.34(19) .
C16 N1 C17 C18 0.19(17) .
N1 C17 C18 C19 0.20(18) .
C17 C18 C19 C15 -0.31(15) .
C17 C18 C19 C20 -179.46(10) .
C16 C15 C19 C18 0.07(16) .
C16 C15 C19 C20 179.27(10) .
C21 N2 C20 C19 88.92(12) .
C18 C19 C20 N2 -5.34(15) .
C15 C19 C20 N2 175.53(9) .
C20 N2 C21 O3 -9.77(16) .
C20 N2 C21 C21 170.11(10) 2_577
