#------------------------------------------------------------------------------
#$Date: 2019-11-26 13:42:55 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243447 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/76/4037608.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_4037608
loop_
_publ_author_name
'Katayama, Katsushi'
'Okamura, Takuya'
'Sunadome, Takuya'
'Nakagawa, Koji'
'Takeda, Hiroshi'
'Shiro, Motoo'
'Matsuda, Akira'
'Ichikawa, Satoshi'
_publ_section_title
;
 Synthesis and biological evaluation of quinaldopeptin.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2580
_journal_page_last               2590
_journal_paper_doi               10.1021/jo500039d
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C60 H76 N16 O12'
_chemical_formula_sum            'C60 H76 N16 O12'
_chemical_formula_weight         1213.36
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 125.123(9)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   24.4859(5)
_cell_length_b                   11.3635(3)
_cell_length_c                   14.2600(10)
_cell_measurement_reflns_used    16281
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.31
_cell_measurement_theta_min      3.79
_cell_volume                     3245.3(4)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku, 2000-2010)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku, 2000-2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla, 2005)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Rigaku VariMax with RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18842
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1288.00
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.210
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  2338 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.28(27)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     400
_refine_ls_number_reflns         5445
_refine_ls_number_restraints     394
_refine_ls_R_factor_gt           0.0628
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1097P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1826
_reflns_number_gt                3668
_reflns_number_total             5445
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo500039d_si_001.cif
_cod_data_source_block           RGK1904
_cod_original_cell_volume        3245.3(5)
_cod_database_code               4037608
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,+Y,-Z
3 1/2+X,1/2+Y,+Z
4 1/2-X,1/2+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 0.24395(15) 0.4715(4) 0.5738(3) 0.0885(10) Uani 1.0 4 d U
O2 O 0.38278(12) 0.4808(4) 0.62250(19) 0.0822(10) Uani 1.0 4 d U
O3 O 0.57584(13) 0.3553(3) 0.9858(2) 0.0755(9) Uani 1.0 4 d U
O4 O 0.52735(12) 0.3559(3) 0.63228(19) 0.0630(7) Uani 1.0 4 d U
O5 O 0.80360(14) 0.3924(4) 0.8029(2) 0.0835(10) Uani 1.0 4 d U
O6 O 0.64742(13) 0.6683(3) 0.6657(2) 0.0752(9) Uani 1.0 4 d U
N1 N 0.22416(16) 0.5772(4) 0.4203(3) 0.0701(10) Uani 1.0 4 d U
N2 N 0.35765(19) 0.5909(5) 0.7268(3) 0.0940(13) Uani 1.0 4 d U
N3 N 0.49309(13) 0.3905(3) 0.8008(3) 0.0592(8) Uani 1.0 4 d U
N4 N 0.62095(15) 0.3225(4) 0.8113(3) 0.0692(10) Uani 1.0 4 d U
N5 N 0.71146(15) 0.3998(4) 0.6226(3) 0.0747(11) Uani 1.0 4 d U
N6 N 0.58918(14) 0.5046(4) 0.5701(3) 0.0602(9) Uani 1.0 4 d U
N7 N 0.51032(15) 0.6356(4) 0.3775(3) 0.0641(9) Uani 1.0 4 d U
N8 N 0.55491(19) 0.8579(5) 0.3653(4) 0.1100(16) Uani 1.0 4 d U
C1 C 0.18552(18) 0.4803(6) 0.3415(3) 0.0778(13) Uani 1.0 4 d U
C2 C 0.11615(19) 0.5276(6) 0.2436(4) 0.0914(15) Uani 1.0 4 d U
C3 C 0.1201(2) 0.6425(6) 0.1903(4) 0.0946(15) Uani 1.0 4 d U
C4 C 0.1616(3) 0.7328(6) 0.2793(4) 0.0933(15) Uani 1.0 4 d U
C5 C 0.2294(3) 0.6870(6) 0.3706(4) 0.0858(13) Uani 1.0 4 d U
C6 C 0.2555(2) 0.5601(6) 0.5342(4) 0.0774(12) Uani 1.0 4 d U
C7 C 0.3031(3) 0.6497(6) 0.6199(4) 0.0893(14) Uani 1.0 4 d U
C8 C 0.3713(4) 0.6271(7) 0.8340(5) 0.118(3) Uani 1.0 4 d U
C9 C 0.39514(18) 0.5121(6) 0.7157(3) 0.0775(12) Uani 1.0 4 d U
C10 C 0.45804(17) 0.4702(4) 0.8275(3) 0.0596(10) Uani 1.0 4 d U
C11 C 0.55029(18) 0.3376(4) 0.8831(3) 0.0603(10) Uani 1.0 4 d U
C12 C 0.5804(2) 0.2561(5) 0.8395(3) 0.0644(10) Uani 1.0 4 d U
C13 C 0.6208(3) 0.1543(5) 0.9230(4) 0.0842(13) Uani 1.0 4 d U
C14 C 0.6893(3) 0.1889(6) 1.0230(4) 0.0952(15) Uani 1.0 4 d U
C15 C 0.7262(3) 0.2478(7) 0.9802(4) 0.0968(16) Uani 1.0 4 d U
C16 C 0.68782(18) 0.3534(6) 0.9066(4) 0.0813(13) Uani 1.0 4 d U
C17 C 0.58747(18) 0.3676(4) 0.7023(3) 0.0624(10) Uani 1.0 4 d U
C18 C 0.63025(18) 0.4284(5) 0.6695(3) 0.0642(11) Uani 1.0 4 d U
C19 C 0.66778(19) 0.3353(5) 0.6453(4) 0.0703(11) Uani 1.0 4 d U
C20 C 0.6233(3) 0.2527(5) 0.5500(4) 0.0776(12) Uani 1.0 4 d U
C21 C 0.77546(18) 0.4222(5) 0.7022(3) 0.0737(12) Uani 1.0 4 d U
C22 C 0.60246(18) 0.6155(5) 0.5769(3) 0.0639(10) Uani 1.0 4 d U
C23 C 0.56223(18) 0.6877(5) 0.4651(3) 0.0637(10) Uani 1.0 4 d U
C24 C 0.47717(18) 0.6977(5) 0.2761(3) 0.0644(10) Uani 1.0 4 d U
C25 C 0.4218(2) 0.6469(5) 0.1764(3) 0.0725(11) Uani 1.0 4 d U
C26 C 0.3895(2) 0.7034(6) 0.0753(4) 0.0772(12) Uani 1.0 4 d U
C27 C 0.4108(2) 0.8153(6) 0.0697(4) 0.0959(16) Uani 1.0 4 d U
C28 C 0.4663(3) 0.8649(7) 0.1643(5) 0.1129(19) Uani 1.0 4 d U
C29 C 0.5006(2) 0.8059(5) 0.2696(4) 0.0827(13) Uani 1.0 4 d U
C30 C 0.5843(3) 0.7972(5) 0.4582(4) 0.0836(14) Uani 1.0 4 d U
H1 H 0.1787 0.4194 0.3846 0.0933 Uiso 1.0 4 calc R
H2A H 0.0930 0.4669 0.1829 0.1096 Uiso 1.0 4 calc R
H2B H 0.0891 0.5418 0.2739 0.1096 Uiso 1.0 4 calc R
H3A H 0.1394 0.6254 0.1469 0.1135 Uiso 1.0 4 calc R
H3B H 0.0745 0.6738 0.1356 0.1135 Uiso 1.0 4 calc R
H3 H 0.4766 0.3760 0.7285 0.0711 Uiso 1.0 4 calc R
H4A H 0.1387 0.7583 0.3147 0.1119 Uiso 1.0 4 calc R
H4B H 0.1662 0.8023 0.2425 0.1119 Uiso 1.0 4 calc R
H5A H 0.2549 0.6718 0.3375 0.1029 Uiso 1.0 4 calc R
H5B H 0.2539 0.7469 0.4316 0.1029 Uiso 1.0 4 calc R
H5 H 0.6941 0.4247 0.5523 0.0896 Uiso 1.0 4 calc R
H6 H 0.5553 0.4749 0.5053 0.0722 Uiso 1.0 4 calc R
H7A H 0.3224 0.6962 0.5868 0.1072 Uiso 1.0 4 calc R
H7B H 0.2788 0.7043 0.6378 0.1072 Uiso 1.0 4 calc R
H8A H 0.3771 0.5575 0.8796 0.1420 Uiso 1.0 4 calc R
H8B H 0.3340 0.6742 0.8207 0.1420 Uiso 1.0 4 calc R
H8C H 0.4122 0.6743 0.8755 0.1420 Uiso 1.0 4 calc R
H10A H 0.4869 0.5383 0.8714 0.0715 Uiso 1.0 4 calc R
H10B H 0.4461 0.4296 0.8748 0.0715 Uiso 1.0 4 calc R
H12 H 0.5425 0.2201 0.7667 0.0773 Uiso 1.0 4 calc R
H13A H 0.5956 0.1225 0.9523 0.1010 Uiso 1.0 4 calc R
H13B H 0.6250 0.0905 0.8803 0.1010 Uiso 1.0 4 calc R
H14A H 0.7141 0.1182 1.0682 0.1142 Uiso 1.0 4 calc R
H14B H 0.6858 0.2435 1.0734 0.1142 Uiso 1.0 4 calc R
H15A H 0.7326 0.1909 0.9347 0.1161 Uiso 1.0 4 calc R
H15B H 0.7708 0.2732 1.0463 0.1161 Uiso 1.0 4 calc R
H16A H 0.6853 0.4134 0.9544 0.0975 Uiso 1.0 4 calc R
H16B H 0.7121 0.3884 0.8769 0.0975 Uiso 1.0 4 calc R
H18 H 0.6643 0.4783 0.7355 0.0771 Uiso 1.0 4 calc R
H19 H 0.6969 0.2878 0.7166 0.0843 Uiso 1.0 4 calc R
H20A H 0.5963 0.2968 0.4780 0.0932 Uiso 1.0 4 calc R
H20B H 0.5938 0.2128 0.5655 0.0932 Uiso 1.0 4 calc R
H20C H 0.6504 0.1943 0.5436 0.0932 Uiso 1.0 4 calc R
H25 H 0.4069 0.5712 0.1807 0.0869 Uiso 1.0 4 calc R
H26 H 0.3525 0.6675 0.0084 0.0927 Uiso 1.0 4 calc R
H27 H 0.3865 0.8577 -0.0005 0.1151 Uiso 1.0 4 calc R
H28 H 0.4815 0.9395 0.1584 0.1355 Uiso 1.0 4 calc R
H30 H 0.6230 0.8291 0.5254 0.1003 Uiso 1.0 4 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, 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_publ_flag
_geom_angle_site_symmetry_3
C1 N1 C5 117.6(4) yes .
C1 N1 C6 118.9(5) yes .
C5 N1 C6 123.5(4) yes .
C7 N2 C8 119.3(6) yes .
C7 N2 C9 116.5(5) yes .
C8 N2 C9 124.0(4) yes .
C10 N3 C11 122.0(4) yes .
C12 N4 C16 116.3(4) yes .
C12 N4 C17 116.3(3) yes .
C16 N4 C17 126.1(5) yes .
C19 N5 C21 123.7(4) yes .
C18 N6 C22 120.2(3) yes .
C23 N7 C24 115.7(4) yes .
C29 N8 C30 116.1(5) yes .
N1 C1 C2 108.6(5) yes .
N1 C1 C21 110.6(4) yes 2_656
C2 C1 C21 113.2(4) yes 2_656
C1 C2 C3 113.1(4) yes .
C2 C3 C4 111.7(5) yes .
C3 C4 C5 112.0(6) yes .
N1 C5 C4 110.5(5) yes .
O1 C6 N1 122.1(5) yes .
O1 C6 C7 116.5(5) yes .
N1 C6 C7 121.3(5) yes .
N2 C7 C6 110.4(5) yes .
O2 C9 N2 123.6(4) yes .
O2 C9 C10 120.8(5) yes .
N2 C9 C10 115.4(4) yes .
N3 C10 C9 108.5(4) yes .
O3 C11 N3 121.7(5) yes .
O3 C11 C12 123.3(4) yes .
N3 C11 C12 114.9(4) yes .
N4 C12 C11 111.1(4) yes .
N4 C12 C13 111.2(5) yes .
C11 C12 C13 112.8(5) yes .
C12 C13 C14 114.0(5) yes .
C13 C14 C15 109.6(5) yes .
C14 C15 C16 110.8(5) yes .
N4 C16 C15 112.0(5) yes .
O4 C17 N4 122.7(5) yes .
O4 C17 C18 120.8(4) yes .
N4 C17 C18 116.4(3) yes .
N6 C18 C17 110.7(4) yes .
N6 C18 C19 110.6(4) yes .
C17 C18 C19 110.7(4) yes .
N5 C19 C18 107.7(4) yes .
N5 C19 C20 110.8(5) yes .
C18 C19 C20 114.5(4) yes .
O5 C21 N5 122.6(5) yes .
O5 C21 C1 121.6(4) yes 2_656
N5 C21 C1 115.7(4) yes 2_656
O6 C22 N6 125.5(4) yes .
O6 C22 C23 117.2(5) yes .
N6 C22 C23 117.3(3) yes .
N7 C23 C22 116.0(5) yes .
N7 C23 C30 123.2(4) yes .
C22 C23 C30 120.6(4) yes .
N7 C24 C25 119.6(5) yes .
N7 C24 C29 120.7(4) yes .
C25 C24 C29 119.6(4) yes .
C24 C25 C26 121.2(5) yes .
C25 C26 C27 119.3(4) yes .
C26 C27 C28 120.7(5) yes .
C27 C28 C29 120.2(7) yes .
N8 C29 C24 121.1(5) yes .
N8 C29 C28 120.0(6) yes .
C24 C29 C28 118.8(4) yes .
N8 C30 C23 123.1(4) yes .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_2
O1 C6 1.264(8) yes .
O2 C9 1.234(6) yes .
O3 C11 1.233(5) yes .
O4 C17 1.221(4) yes .
O5 C21 1.230(5) yes .
O6 C22 1.254(5) yes .
N1 C1 1.466(6) yes .
N1 C5 1.477(8) yes .
N1 C6 1.353(6) yes .
N2 C7 1.487(6) yes .
N2 C8 1.424(9) yes .
N2 C9 1.356(8) yes .
N3 C10 1.441(7) yes .
N3 C11 1.345(5) yes .
N4 C12 1.475(8) yes .
N4 C16 1.446(5) yes .
N4 C17 1.372(5) yes .
N5 C19 1.478(7) yes .
N5 C21 1.328(5) yes .
N6 C18 1.460(5) yes .
N6 C22 1.290(7) yes .
N7 C23 1.304(5) yes .
N7 C24 1.378(6) yes .
N8 C29 1.376(6) yes .
N8 C30 1.285(7) yes .
C1 C2 1.548(6) yes .
C1 C21 1.556(8) yes 2_656
C2 C3 1.541(10) yes .
C3 C4 1.487(8) yes .
C4 C5 1.496(7) yes .
C6 C7 1.499(7) yes .
C9 C10 1.521(5) yes .
C11 C12 1.522(8) yes .
C12 C13 1.542(7) yes .
C13 C14 1.499(6) yes .
C14 C15 1.508(10) yes .
C15 C16 1.513(9) yes .
C17 C18 1.536(8) yes .
C18 C19 1.564(8) yes .
C19 C20 1.487(7) yes .
C22 C23 1.543(6) yes .
C23 C30 1.382(8) yes .
C24 C25 1.406(5) yes .
C24 C29 1.382(8) yes .
C25 C26 1.344(7) yes .
C26 C27 1.394(9) yes .
C27 C28 1.369(7) yes .
C28 C29 1.399(8) yes .
