#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/70/1507048.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_1507048
loop_
_publ_author_name
'Higham, Luke T.'
'Kreher, Ulf P.'
'Raston, Colin L.'
'Scott, Janet L.'
'Strauss, Christopher R.'
_publ_section_title
;
 A new family of macrocycles produced by sequential Claisen-Schmidt
 condensations.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              3257
_journal_page_last               3259
_journal_paper_doi               10.1021/ol048922k
_journal_volume                  6
_journal_year                    2004
_chemical_formula_moiety         '(C44 H40 O6)2 (C2 H3 N1) (C1 H2 Cl2)1.5'
_chemical_formula_sum            'C91.5 H86 Cl3 N O12'
_chemical_formula_weight         1497.96
_chemical_name_systematic
; 
3,4:9,10:18,19:24,25-Tetrabenzo-5,8,20,23-tetraoxa-tricyclo[25.3.1.112,16]-dotriaconta-1,3,9,11,16,18,24,26-octaene-31,32-dione acetonitrile dichloromethane solvate
;
_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                 107.302(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   18.0398(5)
_cell_length_b                   8.8290(5)
_cell_length_c                   25.0282(2)
_cell_measurement_temperature    123(2)
_cell_volume                     3805.9(2)
_computing_cell_refinement       'Nonius collect'
_computing_data_collection       'Nonius collect'
_computing_data_reduction        'Nonius collect'
_computing_molecular_graphics    X-Seed
_computing_publication_material  ciftab
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Enraf Nonius Kappa 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  0.1129
_diffrn_reflns_av_sigmaI/netI    0.2630
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10448
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         3.29
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             1578
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.872
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4537
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.2822
_refine_ls_R_factor_gt           0.1016
_refine_ls_shift/su_max          0.571
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1205P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2066
_refine_ls_wR_factor_ref         0.2711
_reflns_number_gt                1596
_reflns_number_total             4537
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol048922ksi20040609_112119.cif
_cod_data_source_block           2c
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C91.50 H86 Cl3 N O12'
_cod_database_code               1507048
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
O2 O 0.22257(17) 0.8552(3) 0.17700(13) 0.0375(9) Uani 1 1 d . . .
O3 O 0.29180(17) 0.8973(3) 0.29673(13) 0.0406(9) Uani 1 1 d . . .
O1 O 0.44328(17) 0.9413(4) 0.12147(15) 0.0435(9) Uani 1 1 d . . .
C2 C 0.5121(3) 0.7332(5) 0.0990(2) 0.0345(12) Uani 1 1 d . . .
C17 C 0.2767(3) 0.8209(5) 0.3408(2) 0.0359(12) Uani 1 1 d . . .
C15 C 0.1789(3) 0.9058(5) 0.2128(2) 0.0393(13) Uani 1 1 d . . .
H15A H 0.1560 0.8180 0.2267 0.047 Uiso 1 1 calc R . .
H15B H 0.1362 0.9729 0.1918 0.047 Uiso 1 1 calc R . .
C7 C 0.5041(3) 0.5818(5) 0.0707(2) 0.0339(12) Uani 1 1 d . . .
H7A H 0.5542 0.5272 0.0833 0.041 Uiso 1 1 calc R . .
H7B H 0.4908 0.5963 0.0297 0.041 Uiso 1 1 calc R . .
C10 C 0.1832(3) 0.7750(5) 0.1306(2) 0.0358(12) Uani 1 1 d . . .
C11 C 0.1057(3) 0.7317(5) 0.1187(2) 0.0371(12) Uani 1 1 d . . .
H11 H 0.0772 0.7583 0.1437 0.044 Uiso 1 1 calc R . .
C14 C 0.1890(3) 0.6522(5) 0.0467(2) 0.0364(13) Uani 1 1 d . . .
H14 H 0.2173 0.6241 0.0217 0.044 Uiso 1 1 calc R . .
C3 C 0.4411(3) 0.8089(6) 0.10589(19) 0.0352(12) Uani 1 1 d . . .
C8 C 0.3073(3) 0.7852(5) 0.10576(19) 0.0362(12) Uani 1 1 d . . .
H8 H 0.3194 0.8771 0.1263 0.043 Uiso 1 1 calc R . .
C19 C 0.3305(3) 0.6945(5) 0.4286(2) 0.0398(13) Uani 1 1 d . . .
H19 H 0.3742 0.6613 0.4580 0.048 Uiso 1 1 calc R . .
C18 C 0.3418(3) 0.7709(5) 0.38239(19) 0.0317(12) Uani 1 1 d . . .
C4 C 0.3661(3) 0.7208(5) 0.09156(19) 0.0323(11) Uani 1 1 d . . .
C5 C 0.3634(3) 0.5681(5) 0.0646(2) 0.0370(12) Uani 1 1 d . . .
H5A H 0.3484 0.5807 0.0234 0.044 Uiso 1 1 calc R . .
H5B H 0.3233 0.5052 0.0736 0.044 Uiso 1 1 calc R . .
C21 C 0.1920(3) 0.7148(5) 0.3885(2) 0.0432(13) Uani 1 1 d . . .
H21 H 0.1409 0.6934 0.3898 0.052 Uiso 1 1 calc R . .
C16 C 0.2326(3) 0.9907(5) 0.2610(2) 0.0407(13) Uani 1 1 d . . .
H16A H 0.2575 1.0739 0.2462 0.049 Uiso 1 1 calc R . .
H16B H 0.2016 1.0366 0.2835 0.049 Uiso 1 1 calc R . .
C20 C 0.2559(3) 0.6669(5) 0.4318(2) 0.0427(13) Uani 1 1 d . . .
H20 H 0.2487 0.6157 0.4633 0.051 Uiso 1 1 calc R . .
C13 C 0.1107(3) 0.6090(5) 0.0336(2) 0.0437(14) Uani 1 1 d . . .
H13 H 0.0862 0.5536 0.0005 0.052 Uiso 1 1 calc R . .
C22 C 0.2029(3) 0.7934(5) 0.3439(2) 0.0389(13) Uani 1 1 d . . .
H22 H 0.1592 0.8288 0.3150 0.047 Uiso 1 1 calc R . .
C6 C 0.4411(3) 0.4872(5) 0.0841(2) 0.0423(13) Uani 1 1 d . . .
H6A H 0.4371 0.3876 0.0654 0.051 Uiso 1 1 calc R . .
H6B H 0.4551 0.4697 0.1250 0.051 Uiso 1 1 calc R . .
C12 C 0.0703(3) 0.6502(5) 0.0707(2) 0.0413(13) Uani 1 1 d . . .
H12 H 0.0174 0.6219 0.0629 0.050 Uiso 1 1 calc R . .
C1 C 0.5801(3) 0.8081(5) 0.1206(2) 0.0377(12) Uani 1 1 d . . .
H1 H 0.5767 0.8979 0.1406 0.045 Uiso 1 1 calc R . .
C9 C 0.2270(3) 0.7334(5) 0.0941(2) 0.0310(11) Uani 1 1 d . . .
C2G C 0.5000 1.6602(15) 0.2500 0.049(4) Uiso 0.50 2 d SPD A 1
H2G1 H 0.4489 1.6972 0.2503 0.074 Uiso 0.25 1 calc PR A 1
H2G2 H 0.5113 1.6972 0.2163 0.074 Uiso 0.25 1 calc PR A 1
H2G3 H 0.5398 1.6972 0.2833 0.074 Uiso 0.25 1 calc PR A 1
C3G C 0.5000 1.502(2) 0.2500 0.082(6) Uiso 0.50 2 d SPD A 1
C1G C 0.5000 1.1184(18) 0.2500 0.209(10) Uiso 0.75 2 d SPD . 2
Cl1 Cl 0.5000 1.3077(4) 0.2500 0.0564(13) Uani 0.50 2 d SPD A 2
Cl2 Cl 0.58065(16) 1.0235(3) 0.25120(13) 0.0617(9) Uani 0.50 1 d PD B 2
N1G N 0.5000 1.369(3) 0.2500 0.100 Uiso 0.50 2 d SPD . .
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'
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
C10 O2 C15 116.8(4) . .
C17 O3 C16 119.3(4) . .
C1 C2 C3 116.0(4) . .
C1 C2 C7 124.9(4) . .
C3 C2 C7 119.1(4) . .
C22 C17 O3 123.6(5) . .
C22 C17 C18 121.1(5) . .
O3 C17 C18 115.3(4) . .
O2 C15 C16 108.4(4) . .
C2 C7 C6 110.9(4) . .
O2 C10 C11 123.9(4) . .
O2 C10 C9 115.6(4) . .
C11 C10 C9 120.5(5) . .
C12 C11 C10 120.1(5) . .
C9 C14 C13 123.4(5) . .
O1 C3 C2 120.8(4) . .
O1 C3 C4 120.5(4) . .
C2 C3 C4 118.6(4) . .
C4 C8 C9 128.9(5) . .
C20 C19 C18 120.7(5) . .
C17 C18 C19 118.2(4) . .
C17 C18 C1 120.1(4) . 2_655
C19 C18 C1 121.6(5) . 2_655
C8 C4 C5 125.2(4) . .
C8 C4 C3 116.3(4) . .
C5 C4 C3 118.5(4) . .
C4 C5 C6 111.9(4) . .
C22 C21 C20 119.9(5) . .
O3 C16 C15 113.4(4) . .
C21 C20 C19 119.5(5) . .
C12 C13 C14 117.6(5) . .
C17 C22 C21 120.6(5) . .
C5 C6 C7 110.3(4) . .
C11 C12 C13 121.3(5) . .
C2 C1 C18 129.6(4) . 2_655
C14 C9 C10 117.1(4) . .
C14 C9 C8 122.9(4) . .
C10 C9 C8 119.8(4) . .
N1G C3G C2G 180.000(14) . .
Cl1 C1G Cl2 120.1(5) . 2_655
Cl1 C1G Cl2 120.1(5) . .
Cl2 C1G Cl2 119.8(9) 2_655 .
N1G Cl1 C1G 180.00(2) . .
Cl1 N1G C3G 180.00(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C10 1.366(5) .
O2 C15 1.428(5) .
O3 C17 1.387(5) .
O3 C16 1.432(5) .
O1 C3 1.229(5) .
C2 C1 1.356(6) .
C2 C3 1.500(6) .
C2 C7 1.500(6) .
C17 C22 1.378(6) .
C17 C18 1.391(6) .
C15 C16 1.504(6) .
C7 C6 1.526(6) .
C10 C11 1.392(6) .
C10 C9 1.423(6) .
C11 C12 1.385(7) .
C14 C9 1.380(7) .
C14 C13 1.406(6) .
C3 C4 1.508(7) .
C8 C4 1.342(6) .
C8 C9 1.462(6) .
C19 C20 1.394(6) .
C19 C18 1.405(6) .
C18 C1 1.470(6) 2_655
C4 C5 1.502(6) .
C5 C6 1.517(6) .
C21 C22 1.378(7) .
C21 C20 1.393(7) .
C13 C12 1.387(7) .
C1 C18 1.470(6) 2_655
C2G C3G 1.400(19) .
C3G N1G 1.170(15) .
C1G Cl1 1.671(15) .
C1G Cl2 1.672(8) 2_655
C1G Cl2 1.672(8) .
Cl1 N1G 0.54(2) .
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
C16 O3 C17 C22 19.0(6) . .
C16 O3 C17 C18 -161.7(4) . .
C10 O2 C15 C16 179.9(3) . .
C1 C2 C7 C6 143.9(5) . .
C3 C2 C7 C6 -34.5(6) . .
C15 O2 C10 C11 -4.7(6) . .
C15 O2 C10 C9 176.6(4) . .
O2 C10 C11 C12 -179.9(4) . .
C9 C10 C11 C12 -1.2(7) . .
C1 C2 C3 O1 11.9(7) . .
C7 C2 C3 O1 -169.6(4) . .
C1 C2 C3 C4 -170.0(4) . .
C7 C2 C3 C4 8.5(6) . .
C22 C17 C18 C19 -1.5(7) . .
O3 C17 C18 C19 179.1(4) . .
C22 C17 C18 C1 -177.1(4) . 2_655
O3 C17 C18 C1 3.6(6) . 2_655
C20 C19 C18 C17 1.4(7) . .
C20 C19 C18 C1 176.9(4) . 2_655
C9 C8 C4 C5 -6.7(8) . .
C9 C8 C4 C3 175.2(4) . .
O1 C3 C4 C8 -10.9(7) . .
C2 C3 C4 C8 171.0(4) . .
O1 C3 C4 C5 170.9(4) . .
C2 C3 C4 C5 -7.2(6) . .
C8 C4 C5 C6 -145.6(5) . .
C3 C4 C5 C6 32.4(6) . .
C17 O3 C16 C15 -87.9(5) . .
O2 C15 C16 O3 -65.4(5) . .
C22 C21 C20 C19 -2.2(7) . .
C18 C19 C20 C21 0.4(7) . .
C9 C14 C13 C12 -0.4(7) . .
O3 C17 C22 C21 179.1(4) . .
C18 C17 C22 C21 -0.2(7) . .
C20 C21 C22 C17 2.1(7) . .
C4 C5 C6 C7 -59.0(5) . .
C2 C7 C6 C5 59.8(5) . .
C10 C11 C12 C13 0.4(7) . .
C14 C13 C12 C11 0.4(7) . .
C3 C2 C1 C18 -175.4(4) . 2_655
C7 C2 C1 C18 6.3(8) . 2_655
C13 C14 C9 C10 -0.4(6) . .
C13 C14 C9 C8 -176.4(4) . .
O2 C10 C9 C14 180.0(4) . .
C11 C10 C9 C14 1.2(6) . .
O2 C10 C9 C8 -3.9(6) . .
C11 C10 C9 C8 177.4(4) . .
C4 C8 C9 C14 -31.0(7) . .
C4 C8 C9 C10 153.0(5) . .
Cl2 C1G Cl1 N1G -179(100) 2_655 .
Cl2 C1G Cl1 N1G 1(100) . .
C1G Cl1 N1G C3G 0(100) . .
C2G C3G N1G Cl1 0(100) . .
