#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/53/1505384.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_1505384
loop_
_publ_author_name
'Abramite, Joseph A.'
'Sammakia, Tarek'
_publ_section_title
;
 Application of the intramolecular Yamamoto vinylogous aldol reaction to
 the synthesis of macrolides.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2103
_journal_page_last               2106
_journal_paper_doi               10.1021/ol0704901
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C21 H18 N2 O8'
_chemical_formula_sum            'C21 H18 N2 O8'
_chemical_formula_weight         426.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           i
_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_method           SHELXL-97
_cell_angle_alpha                103.3440(10)
_cell_angle_beta                 111.1300(10)
_cell_angle_gamma                99.1780(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4598(5)
_cell_length_b                   11.1436(7)
_cell_length_c                   11.9093(7)
_cell_measurement_reflns_used    4936
_cell_measurement_temperature    148(2)
_cell_measurement_theta_max      38.5165
_cell_measurement_theta_min      2.574
_cell_volume                     981.85(10)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELLXTL'
_computing_molecular_graphics    'Bruker XSCANS'
_computing_publication_material  'Bruker XSCANS'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      148(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0935
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6396
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0576
_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)+(0.0671P)²+0.2670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1613
_reflns_number_gt                3352
_reflns_number_total             3898
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0704901si20070226_075120.cif
_cod_data_source_block           afs55
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1505384
loop_
_symmetry_equiv_pos_as_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
O3 O 0.31921(14) 0.27474(12) 0.35340(10) 0.0283(3) Uani 1 1 d .
O2 O 0.42502(15) 0.41711(11) 0.74841(11) 0.0288(3) Uani 1 1 d .
O4 O 0.61054(15) 0.37147(12) 0.44241(11) 0.0318(3) Uani 1 1 d .
C16 C 0.4698(2) 0.25422(15) 0.22197(15) 0.0256(4) Uani 1 1 d .
C15 C 0.4765(2) 0.30804(15) 0.35204(15) 0.0245(3) Uani 1 1 d .
C14 C 0.3103(2) 0.30424(16) 0.47906(15) 0.0259(4) Uani 1 1 d .
H14A H 0.4082 0.3803 0.5416 0.031 Uiso 1 1 calc R
N2 N 0.79005(19) 0.26349(16) 0.07373(14) 0.0341(4) Uani 1 1 d .
C17 C 0.3166(2) 0.17307(16) 0.12052(15) 0.0272(4) Uani 1 1 d .
H17A H 0.2093 0.1532 0.1297 0.033 Uiso 1 1 calc R
C1 C 0.3259(2) 0.18648(16) 0.52104(15) 0.0263(4) Uani 1 1 d .
C19 C 0.4784(2) 0.14813(16) -0.01245(15) 0.0280(4) Uani 1 1 d .
H19A H 0.4820 0.1103 -0.0913 0.034 Uiso 1 1 calc R
C18 C 0.3259(2) 0.12248(16) 0.00624(15) 0.0282(4) Uani 1 1 d .
C21 C 0.6247(2) 0.28618(16) 0.20645(15) 0.0269(4) Uani 1 1 d .
H21A H 0.7280 0.3440 0.2743 0.032 Uiso 1 1 calc R
N1 N 0.16629(19) 0.03614(15) -0.10199(13) 0.0325(4) Uani 1 1 d .
O5 O 0.18693(19) -0.03946(13) -0.18566(12) 0.0418(4) Uani 1 1 d .
C20 C 0.6246(2) 0.23140(17) 0.08936(16) 0.0276(4) Uani 1 1 d .
C12 C 0.0597(2) 0.36494(16) 0.54578(16) 0.0284(4) Uani 1 1 d .
H12A H -0.0527 0.3804 0.5125 0.034 Uiso 1 1 calc R
C13 C 0.1335(2) 0.33585(17) 0.44848(16) 0.0275(4) Uani 1 1 d .
O1 O 0.27921(19) 0.28992(16) 0.82210(14) 0.0481(4) Uani 1 1 d .
O6 O 0.02400(18) 0.04342(16) -0.10211(14) 0.0488(4) Uani 1 1 d .
O7 O 0.79743(19) 0.19820(17) -0.02155(13) 0.0476(4) Uani 1 1 d .
C6 C 0.4747(2) 0.18426(18) 0.62309(16) 0.0299(4) Uani 1 1 d .
C8 C 0.5892(2) 0.38462(18) 0.81087(16) 0.0314(4) Uani 1 1 d .
H8A H 0.5736 0.3344 0.8675 0.038 Uiso 1 1 calc R
C2 C 0.1890(2) 0.07457(17) 0.45131(17) 0.0327(4) Uani 1 1 d .
H2A H 0.0895 0.0757 0.3816 0.039 Uiso 1 1 calc R
C11 C 0.1153(2) 0.37407(17) 0.66784(17) 0.0306(4) Uani 1 1 d .
H11A H 0.0385 0.3969 0.7059 0.037 Uiso 1 1 calc R
C7 C 0.6260(2) 0.30195(19) 0.70641(16) 0.0335(4) Uani 1 1 d .
H7A H 0.6479 0.3535 0.6534 0.040 Uiso 1 1 calc R
H7B H 0.7336 0.2751 0.7455 0.040 Uiso 1 1 calc R
C10 C 0.2790(2) 0.35395(17) 0.75331(16) 0.0297(4) Uani 1 1 d .
O8 O 0.90975(19) 0.35185(17) 0.15579(14) 0.0533(4) Uani 1 1 d .
C5 C 0.4785(3) 0.0694(2) 0.65130(18) 0.0376(4) Uani 1 1 d .
H5A H 0.5783 0.0665 0.7197 0.045 Uiso 1 1 calc R
C4 C 0.3410(3) -0.03979(19) 0.5823(2) 0.0414(5) Uani 1 1 d .
H4A H 0.3463 -0.1164 0.6040 0.050 Uiso 1 1 calc R
C3 C 0.1952(3) -0.03748(19) 0.4814(2) 0.0399(5) Uani 1 1 d .
H3A H 0.1004 -0.1124 0.4334 0.048 Uiso 1 1 calc R
C9 C 0.7317(3) 0.5084(2) 0.8897(2) 0.0453(5) Uani 1 1 d .
H9A H 0.7002 0.5567 0.9547 0.068 Uiso 1 1 calc R
H9B H 0.7434 0.5595 0.8349 0.068 Uiso 1 1 calc R
H9C H 0.8436 0.4891 0.9307 0.068 Uiso 1 1 calc R
H13B H 0.140(3) 0.405(2) 0.4197(19) 0.030(5) Uiso 1 1 d .
H13A H 0.043(3) 0.263(2) 0.375(2) 0.038(6) Uiso 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 0.0000 0.0000 '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 0.0060 '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
C15 O3 C14 117.47(12)
C10 O2 C8 117.22(13)
C21 C16 C17 120.63(15)
C21 C16 C15 117.23(14)
C17 C16 C15 122.12(14)
O4 C15 O3 125.74(15)
O4 C15 C16 122.81(14)
O3 C15 C16 111.44(13)
O3 C14 C1 106.51(13)
O3 C14 C13 101.93(12)
C1 C14 C13 116.34(13)
O8 N2 O7 124.33(16)
O8 N2 C20 118.17(15)
O7 N2 C20 117.50(15)
C18 C17 C16 117.91(15)
C2 C1 C6 119.22(16)
C2 C1 C14 117.93(15)
C6 C1 C14 122.79(15)
C20 C19 C18 116.42(15)
C17 C18 C19 123.48(15)
C17 C18 N1 118.93(15)
C19 C18 N1 117.59(15)
C20 C21 C16 118.29(15)
O6 N1 O5 124.71(15)
O6 N1 C18 118.11(14)
O5 N1 C18 117.18(15)
C19 C20 C21 123.22(15)
C19 C20 N2 118.54(14)
C21 C20 N2 118.24(15)
C11 C12 C13 134.74(16)
C12 C13 C14 122.04(14)
C5 C6 C1 118.24(17)
C5 C6 C7 118.95(16)
C1 C6 C7 122.76(16)
O2 C8 C9 107.97(15)
O2 C8 C7 107.02(13)
C9 C8 C7 113.56(16)
C3 C2 C1 121.51(17)
C12 C11 C10 129.62(16)
C6 C7 C8 112.12(14)
O1 C10 O2 124.31(17)
O1 C10 C11 122.35(16)
O2 C10 C11 113.31(14)
C4 C5 C6 121.71(18)
C5 C4 C3 119.89(18)
C2 C3 C4 119.41(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C15 1.3299(19)
O3 C14 1.4886(19)
O2 C10 1.348(2)
O2 C8 1.468(2)
O4 C15 1.207(2)
C16 C21 1.391(2)
C16 C17 1.396(2)
C16 C15 1.503(2)
C14 C1 1.517(2)
C14 C13 1.526(2)
N2 O8 1.214(2)
N2 O7 1.227(2)
N2 C20 1.476(2)
C17 C18 1.383(2)
C1 C2 1.398(2)
C1 C6 1.408(2)
C19 C20 1.377(2)
C19 C18 1.384(2)
C18 N1 1.473(2)
C21 C20 1.387(2)
N1 O6 1.219(2)
N1 O5 1.232(2)
C12 C11 1.330(3)
C12 C13 1.500(2)
O1 C10 1.204(2)
C6 C5 1.398(3)
C6 C7 1.514(3)
C8 C9 1.514(3)
C8 C7 1.528(3)
C2 C3 1.380(3)
C11 C10 1.481(2)
C5 C4 1.381(3)
C4 C3 1.387(3)
