#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/49/1504917.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_1504917
loop_
_publ_author_name
'Masci, Bernardo'
'Pasquale, Sara'
'Thuéry, Pierre'
_publ_section_title
;
 Supramolecular control of a fast and reversible Diels-Alder reaction.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4835
_journal_page_last               4838
_journal_paper_doi               10.1021/ol801919q
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C67 H78 O7'
_chemical_formula_weight         995.29
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 100.030(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.9291(11)
_cell_length_b                   18.0055(16)
_cell_length_c                   12.6684(6)
_cell_measurement_reflns_used    55960
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      3.07
_cell_volume                     2904.1(4)
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1999)'
_computing_publication_material
'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method       'one φ and seven ω scans with 2° steps'
_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  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            55960
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.07
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_meas      ?
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         5459
_refine_ls_number_restraints     68
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0727
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1643P)²+1.0676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2065
_refine_ls_wR_factor_ref         0.2276
_reflns_number_gt                3993
_reflns_number_total             5459
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol801919q_si_001.cif
_cod_data_source_block           3.acetone
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1504917
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.59678(13) 0.09888(9) -0.01115(14) 0.0378(5) Uani 1 1 d . . .
O2 O 0.70129(13) 0.15495(10) 0.26770(13) 0.0369(5) Uani 1 1 d . . .
O3 O 0.31805(15) -0.12658(10) 0.26270(13) 0.0406(5) Uani 1 1 d . . .
C1 C 0.7524(2) 0.13907(13) -0.07560(19) 0.0337(6) Uani 1 1 d . . .
C2 C 0.68598(19) 0.14272(13) -0.00017(19) 0.0336(6) Uani 1 1 d . . .
C3 C 0.70980(19) 0.18953(13) 0.08893(19) 0.0334(6) Uani 1 1 d . . .
C4 C 0.8001(2) 0.23298(13) 0.09988(19) 0.0343(6) Uani 1 1 d . . .
H4 H 0.8154 0.2645 0.1587 0.041 Uiso 1 1 calc R . .
C5 C 0.8687(2) 0.23113(14) 0.0258(2) 0.0349(6) Uani 1 1 d . A .
C6 C 0.8423(2) 0.18316(14) -0.06096(19) 0.0355(6) Uani 1 1 d . . .
H6 H 0.8866 0.1805 -0.1113 0.043 Uiso 1 1 calc R . .
C7 C 0.9676(2) 0.27998(15) 0.0400(2) 0.0406(6) Uani 1 1 d D . .
C8A C 1.0379(5) 0.2654(4) -0.0410(6) 0.0597(19) Uani 0.615(11) 1 d PU A 1
H8A H 1.0990 0.2965 -0.0258 0.089 Uiso 0.615(11) 1 calc PR A 1
H8B H 1.0005 0.2761 -0.1117 0.089 Uiso 0.615(11) 1 calc PR A 1
H8C H 1.0590 0.2142 -0.0372 0.089 Uiso 0.615(11) 1 calc PR A 1
C9A C 0.9321(4) 0.3626(3) 0.0282(7) 0.0575(18) Uani 0.615(11) 1 d PU A 1
H9A H 0.8958 0.3755 0.0856 0.086 Uiso 0.615(11) 1 calc PR A 1
H9B H 0.8860 0.3693 -0.0392 0.086 Uiso 0.615(11) 1 calc PR A 1
H9C H 0.9926 0.3939 0.0309 0.086 Uiso 0.615(11) 1 calc PR A 1
C10A C 1.0302(6) 0.2697(5) 0.1526(6) 0.063(2) Uani 0.615(11) 1 d PU A 1
H10A H 1.0496 0.2184 0.1634 0.095 Uiso 0.615(11) 1 calc PR A 1
H10B H 0.9879 0.2844 0.2043 0.095 Uiso 0.615(11) 1 calc PR A 1
H10C H 1.0923 0.2998 0.1611 0.095 Uiso 0.615(11) 1 calc PR A 1
C8B C 1.0586(6) 0.2336(6) 0.0079(10) 0.058(3) Uani 0.385(11) 1 d PDU A 2
H8B1 H 1.1220 0.2625 0.0196 0.087 Uiso 0.385(11) 1 calc PR A 2
H8B2 H 1.0413 0.2203 -0.0665 0.087 Uiso 0.385(11) 1 calc PR A 2
H8B3 H 1.0687 0.1893 0.0507 0.087 Uiso 0.385(11) 1 calc PR A 2
C9B C 0.9483(8) 0.3448(6) -0.0354(10) 0.064(3) Uani 0.385(11) 1 d PDU A 2
H9B1 H 0.8903 0.3734 -0.0194 0.096 Uiso 0.385(11) 1 calc PR A 2
H9B2 H 0.9321 0.3270 -0.1078 0.096 Uiso 0.385(11) 1 calc PR A 2
H9B3 H 1.0100 0.3753 -0.0272 0.096 Uiso 0.385(11) 1 calc PR A 2
C10B C 1.0069(9) 0.3020(7) 0.1553(7) 0.051(3) Uani 0.385(11) 1 d PDU A 2
H10D H 1.0062 0.2595 0.2008 0.077 Uiso 0.385(11) 1 calc PR A 2
H10E H 0.9621 0.3399 0.1761 0.077 Uiso 0.385(11) 1 calc PR A 2
H10F H 1.0773 0.3208 0.1622 0.077 Uiso 0.385(11) 1 calc PR A 2
C11 C 0.5098(2) 0.13058(16) -0.0841(2) 0.0413(6) Uani 1 1 d . . .
H11A H 0.5277 0.1346 -0.1552 0.050 Uiso 1 1 calc R . .
H11B H 0.4949 0.1800 -0.0603 0.050 Uiso 1 1 calc R . .
C12 C 0.4151(2) 0.08192(18) -0.0878(2) 0.0493(7) Uani 1 1 d . B .
H12A H 0.4349 0.0310 -0.0992 0.059 Uiso 1 1 calc R . .
H12B H 0.3627 0.0965 -0.1488 0.059 Uiso 1 1 calc R . .
C13 C 0.3658(2) 0.0852(2) 0.0131(2) 0.0586(9) Uani 1 1 d D . .
C14A C 0.3164(4) 0.1538(3) 0.0274(4) 0.0557(15) Uani 0.677(8) 1 d PD B 3
H14A H 0.2633 0.1638 -0.0340 0.084 Uiso 0.677(8) 1 calc PR B 3
H14B H 0.3677 0.1929 0.0355 0.084 Uiso 0.677(8) 1 calc PR B 3
H14C H 0.2846 0.1513 0.0904 0.084 Uiso 0.677(8) 1 calc PR B 3
C14B C 0.2467(5) 0.0702(5) -0.0027(7) 0.046(3) Uani 0.323(8) 1 d PD B 4
H14D H 0.2119 0.0970 -0.0643 0.068 Uiso 0.323(8) 1 calc PR B 4
H14E H 0.2201 0.0862 0.0596 0.068 Uiso 0.323(8) 1 calc PR B 4
H14F H 0.2339 0.0179 -0.0134 0.068 Uiso 0.323(8) 1 calc PR B 4
C15 C 0.6437(2) 0.19055(14) 0.1749(2) 0.0365(6) Uani 1 1 d . . .
H15A H 0.6276 0.2413 0.1917 0.044 Uiso 1 1 calc R . .
H15B H 0.5782 0.1645 0.1508 0.044 Uiso 1 1 calc R . .
C16 C 0.6468(2) 0.15592(15) 0.35655(19) 0.0372(6) Uani 1 1 d . . .
H16A H 0.6144 0.2043 0.3601 0.045 Uiso 1 1 calc R . .
H16B H 0.6972 0.1491 0.4221 0.045 Uiso 1 1 calc R . .
C17 C 0.56239(19) 0.09635(14) 0.35035(18) 0.0333(6) Uani 1 1 d . . .
C18 C 0.4547(2) 0.11400(14) 0.33358(19) 0.0348(6) Uani 1 1 d . . .
C19 C 0.3775(2) 0.05611(14) 0.33738(19) 0.0357(6) Uani 1 1 d . . .
C20 C 0.4104(2) -0.01848(14) 0.35378(18) 0.0355(6) Uani 1 1 d . . .
C21 C 0.5183(2) -0.03619(14) 0.36670(19) 0.0369(6) Uani 1 1 d . . .
C22 C 0.5943(2) 0.02165(14) 0.36578(18) 0.0359(6) Uani 1 1 d . . .
C23 C 0.4170(2) 0.18830(15) 0.3132(2) 0.0413(6) Uani 1 1 d . . .
H23 H 0.4651 0.2259 0.3079 0.050 Uiso 1 1 calc R . .
C24 C 0.3142(3) 0.20552(17) 0.3015(3) 0.0529(8) Uani 1 1 d . . .
H24 H 0.2926 0.2545 0.2893 0.064 Uiso 1 1 calc R . .
C25 C 0.2389(2) 0.14927(18) 0.3078(3) 0.0538(8) Uani 1 1 d . . .
H25 H 0.1681 0.1615 0.3005 0.065 Uiso 1 1 calc R . .
C26 C 0.2694(2) 0.07793(17) 0.3242(2) 0.0442(7) Uani 1 1 d . . .
H26 H 0.2187 0.0417 0.3271 0.053 Uiso 1 1 calc R . .
C27 C 0.5559(2) -0.11121(15) 0.3826(2) 0.0441(7) Uani 1 1 d . . .
H27 H 0.5077 -0.1497 0.3818 0.053 Uiso 1 1 calc R . .
C28 C 0.6598(3) -0.12714(17) 0.3985(2) 0.0547(8) Uani 1 1 d . . .
H28 H 0.6821 -0.1761 0.4100 0.066 Uiso 1 1 calc R . .
C29 C 0.7344(3) -0.07039(18) 0.3979(2) 0.0536(8) Uani 1 1 d . . .
H29 H 0.8055 -0.0820 0.4091 0.064 Uiso 1 1 calc R . .
C30 C 0.7032(2) 0.00114(16) 0.3810(2) 0.0430(7) Uani 1 1 d . . .
H30 H 0.7535 0.0378 0.3792 0.052 Uiso 1 1 calc R . .
C31 C 0.3324(2) -0.08074(15) 0.3570(2) 0.0429(7) Uani 1 1 d . . .
H31A H 0.3565 -0.1115 0.4193 0.052 Uiso 1 1 calc R . .
H31B H 0.2653 -0.0596 0.3651 0.052 Uiso 1 1 calc R . .
C32 C 0.2684(2) -0.08645(15) 0.16980(19) 0.0396(6) Uani 1 1 d . . .
H32A H 0.3136 -0.0463 0.1545 0.048 Uiso 1 1 calc R . .
H32B H 0.2028 -0.0652 0.1827 0.048 Uiso 1 1 calc R . .
O4 O 0.0409(6) -0.0279(5) 0.2657(6) 0.083(2) Uani 0.50 1 d PDU . .
C33 C -0.0312(5) -0.0042(3) 0.2035(8) 0.064(2) Uani 0.50 1 d PDU . .
C34 C -0.0640(7) 0.0722(4) 0.2195(7) 0.069(2) Uani 0.50 1 d PDU . .
H34A H -0.0436 0.0855 0.2935 0.103 Uiso 0.50 1 calc PR . .
H34B H -0.1389 0.0760 0.1993 0.103 Uiso 0.50 1 calc PR . .
H34C H -0.0309 0.1051 0.1759 0.103 Uiso 0.50 1 calc PR . .
C35 C -0.1280(7) -0.0488(6) 0.1660(8) 0.093(3) Uani 0.50 1 d PDU . .
H35A H -0.1093 -0.0946 0.1354 0.139 Uiso 0.50 1 calc PR . .
H35B H -0.1746 -0.0212 0.1129 0.139 Uiso 0.50 1 calc PR . .
H35C H -0.1625 -0.0593 0.2256 0.139 Uiso 0.50 1 calc PR . .
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'
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_3
C2 O1 C11 112.41(18) .
C16 O2 C15 112.64(19) .
C31 O3 C32 111.57(19) .
C2 C1 C6 118.8(2) .
C2 C1 C32 121.7(2) 3_655
C6 C1 C32 119.5(2) 3_655
O1 C2 C1 120.4(2) .
O1 C2 C3 119.1(2) .
C1 C2 C3 120.4(2) .
C4 C3 C2 118.8(2) .
C4 C3 C15 119.7(2) .
C2 C3 C15 121.4(2) .
C3 C4 C5 122.6(2) .
C6 C5 C4 116.6(2) .
C6 C5 C7 122.1(2) .
C4 C5 C7 121.3(2) .
C5 C6 C1 122.8(2) .
C9B C7 C10B 113.6(6) .
C8A C7 C10A 109.4(4) .
C8A C7 C5 114.2(3) .
C9B C7 C5 109.1(4) .
C10B C7 C5 113.3(4) .
C10A C7 C5 109.5(3) .
C9B C7 C8B 107.5(7) .
C10B C7 C8B 104.6(6) .
C5 C7 C8B 108.3(4) .
C8A C7 C9A 107.7(4) .
C10A C7 C9A 107.8(4) .
C5 C7 C9A 108.1(3) .
O1 C11 C12 109.3(2) .
C11 C12 C13 114.2(2) .
C14A C13 C12 113.8(3) .
C12 C13 C14B 115.9(4) .
O2 C15 C3 108.1(2) .
O2 C16 C17 113.46(19) .
C18 C17 C22 119.6(2) .
C18 C17 C16 122.0(2) .
C22 C17 C16 118.4(2) .
C17 C18 C23 122.3(2) .
C17 C18 C19 120.1(2) .
C23 C18 C19 117.6(2) .
C20 C19 C26 122.7(2) .
C20 C19 C18 119.8(2) .
C26 C19 C18 117.5(2) .
C21 C20 C19 119.8(2) .
C21 C20 C31 118.6(2) .
C19 C20 C31 121.6(2) .
C20 C21 C22 120.0(2) .
C20 C21 C27 122.1(3) .
C22 C21 C27 117.9(2) .
C17 C22 C21 120.6(2) .
C17 C22 C30 121.4(2) .
C21 C22 C30 118.0(2) .
C24 C23 C18 122.2(3) .
C23 C24 C25 120.2(3) .
C26 C25 C24 120.2(3) .
C25 C26 C19 122.2(3) .
C28 C27 C21 121.5(3) .
C27 C28 C29 120.6(3) .
C30 C29 C28 120.4(3) .
C29 C30 C22 121.6(3) .
O3 C31 C20 113.2(2) .
O3 C32 C1 109.0(2) 3_655
O4 C33 C34 117.2(8) .
O4 C33 C35 122.3(8) .
C34 C33 C35 107.6(7) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.384(3) .
O1 C11 1.443(3) .
O2 C16 1.428(3) .
O2 C15 1.430(3) .
O3 C31 1.437(3) .
O3 C32 1.434(3) .
C1 C2 1.393(4) .
C1 C6 1.393(4) .
C1 C32 1.511(3) 3_655
C2 C3 1.399(3) .
C3 C4 1.392(4) .
C3 C15 1.497(4) .
C4 C5 1.399(4) .
C5 C6 1.393(4) .
C5 C7 1.537(4) .
C7 C8A 1.508(6) .
C7 C9B 1.500(7) .
C7 C10B 1.514(8) .
C7 C10A 1.524(7) .
C7 C8B 1.553(8) .
C7 C9A 1.556(6) .
C11 C12 1.500(4) .
C12 C13 1.526(4) .
C13 C14A 1.418(5) .
C13 C14B 1.542(7) .
C16 C17 1.522(3) .
C17 C18 1.408(4) .
C17 C22 1.410(4) .
C18 C23 1.432(4) .
C18 C19 1.449(4) .
C19 C20 1.413(4) .
C19 C26 1.434(4) .
C20 C21 1.412(4) .
C20 C31 1.513(4) .
C21 C22 1.433(4) .
C21 C27 1.438(4) .
C22 C30 1.435(4) .
C23 C24 1.348(4) .
C24 C25 1.417(5) .
C25 C26 1.349(4) .
C27 C28 1.355(4) .
C28 C29 1.405(5) .
C29 C30 1.356(4) .
C32 C1 1.511(3) 3_655
O4 C33 1.191(8) .
C33 C34 1.463(8) .
C33 C35 1.493(8) .
