#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:56:09 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180161 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/57/7105781.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_7105781
loop_
_publ_author_name
'Manza Atkinson'
'Ivan Halasz'
'Dejan-Kresimir Bucar'
'Robert Dinnebier'
'Santhana Mariappan'
'Anatoliy Sokolov'
'Leonard MacGillivray'
_publ_section_title
;
 A solid-state trimerisation of a diene diacid affords a bicyclobutyl:
 reactant structure from X-ray powder data and product separation and
 structure determination via co-crystallisation
;
_journal_name_full               Chem.Commun.
_journal_page_first              236
_journal_paper_doi               10.1039/c0cc02204g
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety         'C24 H30 O12, 2(C10 H8 N2), 2(C3 H7 N O)'
_chemical_formula_sum            'C50 H60 N6 O14'
_chemical_formula_weight         969.04
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_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_date             2010-08-03T12:19:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                86.292(5)
_cell_angle_beta                 77.546(5)
_cell_angle_gamma                78.982(5)
_cell_formula_units_Z            1
_cell_length_a                   8.1654(9)
_cell_length_b                   11.7147(13)
_cell_length_c                   13.1518(14)
_cell_measurement_reflns_used    5687
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      1.00
_cell_volume                     1205.4(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Rastop (Valadon, 2004)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8097
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         5.87
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_correction_T_min  0.9730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             514
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.5
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.046
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0713P)²+0.4585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1273
_reflns_number_gt                3463
_reflns_number_total             4184
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            C0CC02204G.TXT
_cod_data_source_block           2
_cod_database_code               7105781
loop_
_space_group_symop_operation_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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2277(2) 1.05236(15) 0.82153(13) 0.0268(4) Uani 1 1 d . . .
C2 C 0.1166(2) 1.12583(14) 0.91028(13) 0.0232(4) Uani 1 1 d . . .
C3 C 0.00016(19) 1.06485(13) 1.00137(12) 0.0203(4) Uani 1 1 d . . .
C4 C -0.1625(2) 1.15173(14) 0.98036(12) 0.0218(4) Uani 1 1 d . . .
C5 C -0.0498(2) 1.19996(14) 0.88028(12) 0.0237(4) Uani 1 1 d . . .
C6 C -0.0548(2) 1.32759(15) 0.86404(13) 0.0283(4) Uani 1 1 d . . .
C7 C -0.0047(2) 1.38727(15) 0.77590(14) 0.0299(4) Uani 1 1 d . . .
C8 C 0.0611(3) 1.32752(17) 0.67495(14) 0.0342(4) Uani 1 1 d . . .
C9 C -0.2295(2) 1.24410(14) 1.06276(13) 0.0240(4) Uani 1 1 d . . .
C10 C 0.2224(2) 1.19837(16) 0.95228(14) 0.0302(4) Uani 1 1 d . . .
C11 C -0.3069(2) 1.10080(15) 0.95451(14) 0.0278(4) Uani 1 1 d . . .
C12 C -0.0084(3) 1.51602(17) 0.77452(16) 0.0420(5) Uani 1 1 d . . .
C13 C 0.2153(2) 0.75568(17) 0.62478(14) 0.0339(4) Uani 1 1 d . . .
C14 C 0.2492(2) 0.68315(16) 0.54112(14) 0.0318(4) Uani 1 1 d . . .
C15 C 0.3790(2) 0.69835(15) 0.45613(13) 0.0271(4) Uani 1 1 d . . .
C16 C 0.4705(2) 0.78608(16) 0.46085(14) 0.0319(4) Uani 1 1 d . . .
C17 C 0.4264(2) 0.85460(16) 0.54799(15) 0.0343(4) Uani 1 1 d . . .
C18 C 0.4200(2) 0.62065(15) 0.36545(13) 0.0270(4) Uani 1 1 d . . .
C19 C 0.4004(2) 0.50543(16) 0.37854(15) 0.0336(4) Uani 1 1 d . . .
C20 C 0.4451(3) 0.43464(16) 0.29358(15) 0.0349(4) Uani 1 1 d . . .
C21 C 0.5165(3) 0.58383(17) 0.18338(15) 0.0395(5) Uani 1 1 d . . .
C22 C 0.4794(3) 0.66023(17) 0.26442(15) 0.0364(5) Uani 1 1 d . . .
C23 C 0.8296(2) 0.82251(17) 0.57580(15) 0.0345(4) Uani 1 1 d . . .
C24 C 0.7540(3) 0.84181(19) 0.76313(16) 0.0446(5) Uani 1 1 d . . .
C25 C 0.8157(3) 1.01091(19) 0.64852(19) 0.0499(6) Uani 1 1 d . . .
H10A H 0.3144 1.1467 0.9785 0.045 Uiso 1 1 calc R . .
H10B H 0.1494 1.2462 1.009 0.045 Uiso 1 1 calc R . .
H10C H 0.2715 1.2489 0.8963 0.045 Uiso 1 1 calc R . .
H11A H -0.3712 1.0692 1.0183 0.042 Uiso 1 1 calc R . .
H11B H -0.2591 1.0385 0.9045 0.042 Uiso 1 1 calc R . .
H11C H -0.3832 1.162 0.9242 0.042 Uiso 1 1 calc R . .
H12A H -0.0628 1.5465 0.8437 0.063 Uiso 1 1 calc R . .
H12B H -0.0734 1.5544 0.7233 0.063 Uiso 1 1 calc R . .
H12C H 0.1084 1.5312 0.7556 0.063 Uiso 1 1 calc R . .
H13 H 0.1268 0.7442 0.6824 0.041 Uiso 1 1 calc R . .
H14 H 0.1847 0.6236 0.5416 0.038 Uiso 1 1 calc R . .
H16 H 0.5616 0.7987 0.4053 0.038 Uiso 1 1 calc R . .
H17 H 0.4892 0.9144 0.5503 0.041 Uiso 1 1 calc R . .
H19 H 0.3564 0.4754 0.4456 0.04 Uiso 1 1 calc R . .
H1O H 0.2104 0.9473 0.7339 0.049 Uiso 1 1 calc R . .
H20 H 0.4342 0.3552 0.3046 0.042 Uiso 1 1 calc R . .
H21 H 0.5536 0.6125 0.1147 0.047 Uiso 1 1 calc R . .
H22 H 0.4941 0.7387 0.2515 0.044 Uiso 1 1 calc R . .
H23 H 0.8589 0.858 0.509 0.041 Uiso 1 1 calc R . .
H24A H 0.7505 0.7589 0.7603 0.067 Uiso 1 1 calc R . .
H24B H 0.6416 0.8834 0.7973 0.067 Uiso 1 1 calc R . .
H24C H 0.8391 0.8514 0.8027 0.067 Uiso 1 1 calc R . .
H25A H 0.8405 1.0342 0.5747 0.075 Uiso 1 1 calc R . .
H25B H 0.9088 1.0221 0.6809 0.075 Uiso 1 1 calc R . .
H25C H 0.7088 1.0585 0.6836 0.075 Uiso 1 1 calc R . .
H3 H 0.0235 1.0828 1.0696 0.024 Uiso 1 1 calc R . .
H4O H -0.4136 1.3555 1.1004 0.054 Uiso 1 1 calc R . .
H5 H -0.071 1.1673 0.8169 0.028 Uiso 1 1 calc R . .
H6 H -0.0996 1.3729 0.9245 0.034 Uiso 1 1 calc R . .
H6O H 0.1159 1.36 0.5388 0.072 Uiso 1 1 calc R . .
N1 N 0.3011(2) 0.84138(14) 0.62856(12) 0.0334(4) Uani 1 1 d . . .
N2 N 0.5028(2) 0.47146(13) 0.19670(12) 0.0339(4) Uani 1 1 d . . .
N3 N 0.7996(2) 0.88882(14) 0.65804(12) 0.0352(4) Uani 1 1 d . . .
O1 O 0.14380(16) 0.98614(11) 0.78255(10) 0.0329(3) Uani 1 1 d . . .
O2 O 0.37799(16) 1.05449(13) 0.78900(11) 0.0421(4) Uani 1 1 d . . .
O3 O -0.14947(17) 1.26727(11) 1.12337(10) 0.0344(3) Uani 1 1 d . . .
O4 O -0.38420(16) 1.30211(12) 1.05690(10) 0.0360(3) Uani 1 1 d . . .
O5 O 0.0977(2) 1.22246(13) 0.66619(12) 0.0601(5) Uani 1 1 d . . .
O6 O 0.0840(2) 1.39874(12) 0.59343(11) 0.0478(4) Uani 1 1 d . . .
O7 O 0.82214(18) 0.71752(12) 0.57972(10) 0.0419(4) 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 0 '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 0.006 '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
C1 C2 C10 110.04(14) . . ?
C1 C2 C3 118.67(13) . . ?
C1 C2 C5 112.70(14) . . ?
C1 O1 H1O 109.5 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
C2 C3 H3 109.1 . . ?
C2 C5 H5 109.4 . . ?
C3 C3 C2 120.17(16) 2_577 . ?
C3 C3 C4 117.64(16) 2_577 . ?
C3 C3 H3 109.1 2_577 . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
C4 C3 C2 90.13(12) . . ?
C4 C3 H3 109.1 . . ?
C4 C5 C2 90.34(12) . . ?
C4 C5 H5 109.4 . . ?
C5 C2 C3 89.03(12) . . ?
C5 C4 C3 89.51(12) . . ?
C5 C6 H6 115.5 . . ?
C6 C5 C2 116.73(14) . . ?
C6 C5 C4 120.22(14) . . ?
C6 C5 H5 109.4 . . ?
C6 C7 C12 122.05(17) . . ?
C6 C7 C8 121.01(16) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
C7 C6 C5 128.96(16) . . ?
C7 C6 H6 115.5 . . ?
C8 C7 C12 116.93(16) . . ?
C8 O6 H6O 109.5 . . ?
C9 C4 C11 111.49(13) . . ?
C9 C4 C3 112.63(13) . . ?
C9 C4 C5 111.30(13) . . ?
C9 O4 H4O 109.5 . . ?
C10 C2 C3 111.62(13) . . ?
C10 C2 C5 113.46(14) . . ?
C11 C4 C3 118.05(13) . . ?
C11 C4 C5 112.01(13) . . ?
C13 C14 C15 119.22(17) . . ?
C13 C14 H14 120.4 . . ?
C14 C13 H13 118.4 . . ?
C14 C15 C16 117.64(16) . . ?
C14 C15 C18 120.49(16) . . ?
C15 C14 H14 120.4 . . ?
C15 C16 H16 120.6 . . ?
C16 C15 C18 121.85(16) . . ?
C16 C17 H17 118.1 . . ?
C17 C16 C15 118.81(17) . . ?
C17 C16 H16 120.6 . . ?
C17 N1 C13 117.43(15) . . ?
C18 C19 H19 120.2 . . ?
C18 C22 H22 120.4 . . ?
C19 C18 C15 120.92(16) . . ?
C19 C18 C22 117.33(16) . . ?
C19 C20 H20 118.2 . . ?
C20 C19 C18 119.53(17) . . ?
C20 C19 H19 120.2 . . ?
C20 N2 C21 116.94(16) . . ?
C21 C22 C18 119.16(17) . . ?
C21 C22 H22 120.4 . . ?
C22 C18 C15 121.76(16) . . ?
C22 C21 H21 118.3 . . ?
C23 N3 C24 121.30(17) . . ?
C23 N3 C25 122.17(18) . . ?
C24 N3 C25 116.50(16) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N1 C13 C14 123.18(17) . . ?
N1 C13 H13 118.4 . . ?
N1 C17 C16 123.71(17) . . ?
N1 C17 H17 118.1 . . ?
N2 C20 C19 123.59(17) . . ?
N2 C20 H20 118.2 . . ?
N2 C21 C22 123.38(18) . . ?
N2 C21 H21 118.3 . . ?
N3 C23 H23 117.6 . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
N3 C25 H25A 109.5 . . ?
N3 C25 H25B 109.5 . . ?
N3 C25 H25C 109.5 . . ?
O1 C1 C2 113.01(14) . . ?
O2 C1 C2 123.75(16) . . ?
O2 C1 O1 123.24(16) . . ?
O3 C9 C4 124.50(15) . . ?
O3 C9 O4 123.12(15) . . ?
O4 C9 C4 112.27(14) . . ?
O5 C8 C7 124.35(17) . . ?
O5 C8 O6 121.51(17) . . ?
O6 C8 C7 114.08(16) . . ?
O7 C23 H23 117.6 . . ?
O7 C23 N3 124.76(18) . . ?
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
C1 C2 1.517(2) . ?
C2 C10 1.523(2) . ?
C3 C2 1.583(2) . ?
C3 C3 1.523(3) 2_577 ?
C3 C4 1.575(2) . ?
C3 H3 1 . ?
C4 C11 1.527(2) . ?
C5 C2 1.579(2) . ?
C5 C4 1.574(2) . ?
C5 C6 1.491(2) . ?
C5 H5 1 . ?
C6 H6 0.95 . ?
C7 C12 1.502(3) . ?
C7 C6 1.342(3) . ?
C7 C8 1.487(3) . ?
C9 C4 1.521(2) . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13 0.95 . ?
C14 C13 1.382(3) . ?
C14 H14 0.95 . ?
C15 C14 1.393(2) . ?
C15 C16 1.393(2) . ?
C16 C17 1.385(3) . ?
C16 H16 0.95 . ?
C17 H17 0.95 . ?
C18 C15 1.488(2) . ?
C18 C19 1.385(3) . ?
C18 C22 1.394(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?
C21 H21 0.95 . ?
C22 C21 1.382(3) . ?
C22 H22 0.95 . ?
C23 H23 0.95 . ?
C23 N3 1.325(2) . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?
N1 C13 1.339(2) . ?
N1 C17 1.328(2) . ?
N2 C20 1.334(3) . ?
N2 C21 1.339(3) . ?
N3 C24 1.453(3) . ?
N3 C25 1.456(3) . ?
O1 C1 1.319(2) . ?
O1 H1O 0.84 . ?
O2 C1 1.214(2) . ?
O3 C9 1.207(2) . ?
O4 C9 1.331(2) . ?
O4 H4O 0.84 . ?
O5 C8 1.217(2) . ?
O6 C8 1.318(2) . ?
O6 H6O 0.84 . ?
O7 C23 1.240(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O N1 0.84 1.85 2.6679(19) 162.9 .
O4 H4O N2 0.84 1.85 2.6848(19) 175.1 1_466
O6 H6O O7 0.84 1.78 2.6225(19) 177.6 2_676
