#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/20/8102022.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_8102022
loop_
_publ_author_name
'Le Bras, G.'
'Bekaert, A.'
'Viossat, B.'
'Peyrat, J.-F.'
'Alami, M.'
'Brion, J. D.'
'Lemoine, P.'
_publ_section_title
;
Crystal structure of cyclonovobiocin, C₄₄H₄₂N₂O₁₂
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              381
_journal_page_last               382
_journal_volume                  221
_journal_year                    2006
_chemical_formula_sum            'C44 H42 N2 O12'
_chemical_formula_weight         790.80
_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
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 99.818(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            2
_cell_length_a                   5.437(5)
_cell_length_b                   32.564(5)
_cell_length_c                   10.922(5)
_cell_measurement_reflns_used    6287
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      0.41
_cell_volume                     1905(2)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'CAMERON(Watkin et al., 1996) [6]'
_computing_publication_material  'WinGX - V. 1.63.02 (Farrugia, 1999)[7)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997) [5]'
_computing_structure_solution    'SIR92(Altomare et al., 1994) [4]'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11738
_diffrn_reflns_theta_full        26.54
_diffrn_reflns_theta_max         26.54
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepipedic
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.213
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0518
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1537
_refine_ls_wR_factor_ref         0.1738
_reflns_number_gt                2756
_reflns_number_total             3855
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1839.cff
_cod_data_source_block           ab99
_cod_original_sg_symbol_H-M      P12(1)/c1
_cod_database_code               8102022
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_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8496(2) 0.19082(4) 0.76563(13) 0.0599(4) Uani 1 4 e d . . .
H1 H 0.7278 0.1864 0.7117 0.072 Uiso 1 4 e calc R . .
C2 C 0.8370(3) 0.22963(6) 0.80956(17) 0.0475(5) Uani 1 4 e d . . .
C3 C 0.6369(3) 0.25573(5) 0.76485(13) 0.0561(5) Uani 1 4 e d . . .
H3 H 0.5081 0.2466 0.7038 0.067 Uiso 1 4 e calc R . .
C4 C 0.6310(3) 0.29484(5) 0.81116(13) 0.0542(5) Uani 1 4 e d R . .
H4 H 0.4971 0.3120 0.7815 0.065 Uiso 1 4 e calc R . .
C5 C 0.8227(3) 0.30918(6) 0.90176(16) 0.0440(4) Uani 1 4 e d . . .
C6 C 1.0192(3) 0.28229(6) 0.94417(16) 0.0416(4) Uani 1 4 e d . . .
C7 C 1.0304(3) 0.24220(6) 0.90183(16) 0.0443(4) Uani 1 4 e d . . .
C8 C 1.2395(4) 0.21341(6) 0.9535(2) 0.0610(6) Uani 1 4 e d . . .
H8A H 1.2151 0.1875 0.9113 0.091 Uiso 1 4 e calc R . .
H8B H 1.2406 0.2094 1.0407 0.091 Uiso 1 4 e calc R . .
H8C H 1.3960 0.2250 0.9415 0.091 Uiso 1 4 e calc R . .
O9 O 1.2153(2) 0.29509(4) 1.03292(11) 0.0478(4) Uani 1 4 e d . . .
C10 C 1.2319(3) 0.33427(6) 1.07654(16) 0.0454(5) Uani 1 4 e d . . .
O11 O 1.4179(2) 0.34311(4) 1.15212(13) 0.0583(4) Uani 1 4 e d . . .
C12 C 1.0358(3) 0.36275(5) 1.03302(16) 0.0442(4) Uani 1 4 e d . . .
C13 C 0.8311(3) 0.35040(6) 0.95011(16) 0.0447(5) Uani 1 4 e d . . .
O14 O 0.6392(3) 0.37427(5) 0.90533(13) 0.0606(4) Uani 1 4 e d . . .
N15 N 1.0890(3) 0.40214(5) 1.08465(15) 0.0546(5) Uani 1 4 e d . . .
H15 H 1.2440 0.4062 1.1141 0.066 Uiso 1 4 e calc R . .
C16 C 0.9405(4) 0.43428(6) 1.09587(17) 0.0482(5) Uani 1 4 e d . . .
O17 O 0.7160(3) 0.43405(5) 1.04881(18) 0.0812(6) Uani 1 4 e d . . .
C18 C 1.0512(3) 0.46918(5) 1.17195(16) 0.0442(4) Uani 1 4 e d . . .
C19 C 1.2886(4) 0.46770(6) 1.24592(18) 0.0520(5) Uani 1 4 e d . . .
H19 H 1.3903 0.4450 1.2415 0.062 Uiso 1 4 e calc R . .
C20 C 1.3723(3) 0.49930(6) 1.32445(19) 0.0513(5) Uani 1 4 e d . . .
H20 H 1.5293 0.4978 1.3738 0.062 Uiso 1 4 e calc R . .
C21 C 1.2229(3) 0.53372(6) 1.33075(17) 0.0453(4) Uani 1 4 e d . . .
C22 C 0.9909(3) 0.53710(5) 1.25441(17) 0.0448(4) Uani 1 4 e d . . .
C23 C 0.9084(3) 0.50435(6) 1.17708(17) 0.0475(5) Uani 1 4 e d . . .
H23 H 0.7522 0.5060 1.1270 0.057 Uiso 1 4 e calc R . .
C24 C 0.8362(4) 0.57523(6) 1.2593(2) 0.0555(5) Uani 1 4 e d . . .
H24A H 0.6982 0.5691 1.3021 0.067 Uiso 1 4 e calc R . .
H24B H 0.7672 0.5837 1.1754 0.067 Uiso 1 4 e calc R . .
C25 C 0.9886(4) 0.61006(6) 1.3255(2) 0.0602(6) Uani 1 4 e d . . .
H25A H 0.8766 0.6311 1.3464 0.072 Uiso 1 4 e calc R . .
H25B H 1.0898 0.6222 1.2699 0.072 Uiso 1 4 e calc R . .
C26 C 1.1578(3) 0.59597(6) 1.44338(19) 0.0505(5) Uani 1 4 e d . . .
O27 O 1.3210(2) 0.56329(4) 1.41281(14) 0.0562(4) Uani 1 4 e d . . .
C28 C 1.3345(5) 0.63016(8) 1.4937(3) 0.0839(8) Uani 1 4 e d . . .
H28A H 1.4377 0.6213 1.5693 0.126 Uiso 1 4 e calc R . .
H28B H 1.2402 0.6539 1.5101 0.126 Uiso 1 4 e calc R . .
H28C H 1.4379 0.6370 1.4336 0.126 Uiso 1 4 e calc R . .
C29 C 1.0156(5) 0.57935(9) 1.5398(2) 0.0809(8) Uani 1 4 e d . . .
H29A H 1.1312 0.5709 1.6119 0.121 Uiso 1 4 e calc R . .
H29B H 0.9170 0.5562 1.5062 0.121 Uiso 1 4 e calc R . .
H29C H 0.9081 0.6004 1.5627 0.121 Uiso 1 4 e calc R . .
H14 H 0.673(6) 0.3982(10) 0.961(3) 0.120(11) Uiso 1 4 e 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'
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'
H H 0.0000 0.0000 '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
O1 C2 C7 116.96(16) . . ?
O1 C2 C3 121.62(15) . . ?
C7 C2 C3 121.42(17) . . ?
C4 C3 C2 119.98(9) . . ?
C3 C4 C5 120.82(10) . . ?
C4 C5 C6 117.61(17) . . ?
C4 C5 C13 123.19(16) . . ?
C6 C5 C13 119.17(16) . . ?
O9 C6 C7 116.48(15) . . ?
O9 C6 C5 119.99(16) . . ?
C7 C6 C5 123.54(16) . . ?
C6 C7 C2 116.59(16) . . ?
C6 C7 C8 122.19(16) . . ?
C2 C7 C8 121.21(18) . . ?
C10 O9 C6 121.85(14) . . ?
O11 C10 O9 117.03(16) . . ?
O11 C10 C12 123.61(18) . . ?
O9 C10 C12 119.37(16) . . ?
C13 C12 N15 128.26(16) . . ?
C13 C12 C10 120.28(17) . . ?
N15 C12 C10 111.46(16) . . ?
O14 C13 C12 124.83(18) . . ?
O14 C13 C5 115.92(16) . . ?
C12 C13 C5 119.19(16) . . ?
C16 N15 C12 131.36(17) . . ?
O17 C16 N15 121.50(19) . . ?
O17 C16 C18 121.08(17) . . ?
N15 C16 C18 117.34(18) . . ?
C23 C18 C19 118.09(17) . . ?
C23 C18 C16 118.73(17) . . ?
C19 C18 C16 123.05(17) . . ?
C20 C19 C18 120.72(17) . . ?
C19 C20 C21 120.16(17) . . ?
O27 C21 C22 123.47(17) . . ?
O27 C21 C20 115.82(17) . . ?
C22 C21 C20 120.69(17) . . ?
C23 C22 C21 118.02(17) . . ?
C23 C22 C24 122.08(17) . . ?
C21 C22 C24 119.89(17) . . ?
C22 C23 C18 122.22(17) . . ?
C22 C24 C25 111.79(17) . . ?
C24 C25 C26 112.41(17) . . ?
O27 C26 C29 107.57(17) . . ?
O27 C26 C28 104.27(17) . . ?
C29 C26 C28 112.3(2) . . ?
O27 C26 C25 109.26(16) . . ?
C29 C26 C25 113.03(19) . . ?
C28 C26 C25 109.9(2) . . ?
C21 O27 C26 118.75(15) . . ?
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 C2 1.358(2) . ?
C2 C7 1.388(3) . ?
C2 C3 1.401(2) . ?
C3 C4 1.3729 . ?
C4 C5 1.390(2) . ?
C5 C6 1.398(3) . ?
C5 C13 1.440(3) . ?
C6 O9 1.377(2) . ?
C6 C7 1.390(3) . ?
C7 C8 1.507(3) . ?
O9 C10 1.359(2) . ?
C10 O11 1.226(2) . ?
C10 C12 1.432(3) . ?
C12 C13 1.370(3) . ?
C12 N15 1.411(2) . ?
C13 O14 1.326(2) . ?
N15 C16 1.340(2) . ?
C16 O17 1.241(3) . ?
C16 C18 1.474(3) . ?
C18 C23 1.390(3) . ?
C18 C19 1.402(3) . ?
C19 C20 1.367(3) . ?
C20 C21 1.393(3) . ?
C21 O27 1.361(2) . ?
C21 C22 1.393(3) . ?
C22 C23 1.387(3) . ?
C22 C24 1.506(3) . ?
C24 C25 1.514(3) . ?
C25 C26 1.520(3) . ?
C26 O27 1.460(2) . ?
C26 C29 1.509(3) . ?
C26 C28 1.512(3) . ?
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
O14 H14 O17 0.99(3) 1.50(3) 2.489(2) 178(3) .
O1 H1 O11 0.82 1.95 2.697(2) 150.5 4_465
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N15 C16 C18 171.05(18) . . . . ?
C10 C12 N15 C16 -160.86(19) . . . . ?
C19 C18 C16 N15 -9.4(3) . . . . ?
C19 C18 C16 O17 167.5(2) . . . . ?
C13 C12 N15 C16 20.1(3) . . . . ?
C23 C18 C16 N15 174.75(17) . . . . ?
C23 C18 C16 O17 -8.3(3) . . . . ?
