#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/56/1515648.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_1515648
loop_
_publ_author_name
'Kummer, David A.'
'Li, Derun'
'Dion, Amelie'
'Myers, Andrew G.'
_publ_section_title
;
 A practical, convergent route to the key precursor to the tetracycline
 antibiotics.
;
_journal_issue                   9
_journal_name_full
'Chemical science (Royal Society of Chemistry : 2010)'
_journal_page_first              1710
_journal_page_last               1718
_journal_paper_doi               10.1039/C1SC00303H
_journal_volume                  2
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H20 N2 O4'
_chemical_formula_weight         352.38
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4713(2)
_cell_length_b                   12.2439(3)
_cell_length_c                   21.5133(6)
_cell_measurement_reflns_used    39693
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.0
_cell_measurement_theta_min      3.11
_cell_volume                     1704.58(8)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 v2009.3.0 (Bruker-AXS, 2009)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2009)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            42649
_diffrn_reflns_theta_full        66.46
_diffrn_reflns_theta_max         66.46
_diffrn_reflns_theta_min         4.11
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  0.8706
_exptl_absorpt_correction_T_min  0.8088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(15)
_refine_ls_extinction_coef       0.0045(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0256
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0431P)²+0.2931P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0696
_reflns_number_gt                2902
_reflns_number_total             2922
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1sc00303h.txt
_cod_data_source_block           RDP
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1515648
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-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
O1 O 0.99494(14) 0.32504(7) 0.60692(4) 0.0211(2) Uani 1 1 d .
O2 O 0.20520(16) 0.53881(8) 0.72637(5) 0.0272(2) Uani 1 1 d .
O3 O 0.50908(15) 0.58251(7) 0.65744(4) 0.0248(2) Uani 1 1 d .
O4 O 0.94872(14) 0.60730(7) 0.59690(4) 0.0218(2) Uani 1 1 d .
N1 N 1.06935(18) 0.42972(9) 0.58583(5) 0.0216(2) Uani 1 1 d .
N2 N 0.59441(16) 0.18646(9) 0.60712(5) 0.0192(2) Uani 1 1 d .
C1 C 0.8174(2) 0.34066(11) 0.63779(5) 0.0189(3) Uani 1 1 d .
C2 C 0.68943(19) 0.24564(10) 0.65922(6) 0.0194(3) Uani 1 1 d .
H2A H 0.7842 0.1936 0.6810 0.023 Uiso 1 1 calc R
C3 C 0.5327(2) 0.28909(11) 0.70835(5) 0.0201(3) Uani 1 1 d .
H3 H 0.6079 0.2898 0.7490 0.024 Uiso 1 1 calc R
C4 C 0.3512(2) 0.21032(12) 0.71651(6) 0.0240(3) Uani 1 1 d .
H4A H 0.2815 0.1995 0.6760 0.029 Uiso 1 1 calc R
H4B H 0.4034 0.1386 0.7308 0.029 Uiso 1 1 calc R
C5 C 0.1985(2) 0.25403(12) 0.76301(6) 0.0282(3) Uani 1 1 d .
H5 H 0.1261 0.2047 0.7892 0.034 Uiso 1 1 calc R
C6 C 0.1632(2) 0.36083(12) 0.76792(6) 0.0270(3) Uani 1 1 d .
H6 H 0.0637 0.3873 0.7967 0.032 Uiso 1 1 calc R
C7 C 0.2777(2) 0.43665(11) 0.72912(6) 0.0237(3) Uani 1 1 d .
C8 C 0.45399(19) 0.40496(11) 0.69823(6) 0.0203(3) Uani 1 1 d .
C9 C 0.5704(2) 0.48545(10) 0.66480(5) 0.0193(3) Uani 1 1 d .
C10 C 0.7662(2) 0.44792(11) 0.63886(5) 0.0189(3) Uani 1 1 d .
C11 C 0.9321(2) 0.49990(10) 0.60599(6) 0.0188(3) Uani 1 1 d .
C12 C 1.1203(2) 0.63998(11) 0.55700(6) 0.0228(3) Uani 1 1 d .
H12A H 1.0886 0.6219 0.5132 0.027 Uiso 1 1 calc R
H12B H 1.2473 0.6003 0.5692 0.027 Uiso 1 1 calc R
C13 C 1.1527(2) 0.76056(11) 0.56368(6) 0.0214(3) Uani 1 1 d .
C14 C 1.0951(2) 0.83205(11) 0.51708(6) 0.0246(3) Uani 1 1 d .
H14 H 1.0310 0.8046 0.4806 0.029 Uiso 1 1 calc R
C15 C 1.1296(2) 0.94308(12) 0.52296(7) 0.0282(3) Uani 1 1 d .
H15 H 1.0866 0.9914 0.4909 0.034 Uiso 1 1 calc R
C16 C 1.2266(2) 0.98415(11) 0.57541(7) 0.0261(3) Uani 1 1 d .
H16 H 1.2498 1.0604 0.5795 0.031 Uiso 1 1 calc R
C17 C 1.2893(2) 0.91317(12) 0.62172(7) 0.0293(3) Uani 1 1 d .
H17 H 1.3576 0.9405 0.6576 0.035 Uiso 1 1 calc R
C18 C 1.2525(2) 0.80225(12) 0.61582(6) 0.0284(3) Uani 1 1 d .
H18 H 1.2960 0.7540 0.6478 0.034 Uiso 1 1 calc R
C19 C 0.5024(2) 0.25689(11) 0.55974(5) 0.0218(3) Uani 1 1 d .
H19A H 0.6117 0.2979 0.5385 0.033 Uiso 1 1 calc R
H19B H 0.4061 0.3080 0.5795 0.033 Uiso 1 1 calc R
H19C H 0.4279 0.2120 0.5294 0.033 Uiso 1 1 calc R
C20 C 0.7362(2) 0.10774(11) 0.57935(6) 0.0249(3) Uani 1 1 d .
H20A H 0.7841 0.0566 0.6113 0.037 Uiso 1 1 calc R
H20B H 0.8550 0.1464 0.5616 0.037 Uiso 1 1 calc R
H20C H 0.6648 0.0673 0.5464 0.037 Uiso 1 1 calc R
H2 H 0.302(3) 0.5757(16) 0.6998(9) 0.048(5) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 O1 N1 108.37(9)
C7 O2 H2 103.7(12)
C11 O4 C12 114.70(10)
C11 N1 O1 104.62(10)
C19 N2 C2 114.30(10)
C20 N2 C2 112.03(10)
C20 N2 C19 111.11(10)
O1 C1 C2 120.96(11)
O1 C1 C10 110.87(11)
C10 C1 C2 127.70(12)
N2 C2 C1 112.26(10)
N2 C2 H2A 107.4
N2 C2 C3 114.41(10)
C1 C2 H2A 107.4
C1 C2 C3 107.62(10)
C3 C2 H2A 107.4
C2 C3 H3 106.2
C4 C3 C2 111.23(10)
C4 C3 H3 106.2
C8 C3 C2 116.03(10)
C8 C3 H3 106.2
C8 C3 C4 110.29(11)
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 108.1
C5 C4 C3 110.88(12)
C5 C4 H4A 109.5
C5 C4 H4B 109.5
C4 C5 H5 119.5
C6 C5 C4 120.96(13)
C6 C5 H5 119.5
C5 C6 H6 120.2
C5 C6 C7 119.67(13)
C7 C6 H6 120.2
O2 C7 C6 116.40(12)
O2 C7 C8 122.22(13)
C8 C7 C6 121.36(13)
C7 C8 C3 118.09(12)
C7 C8 C9 118.95(12)
C9 C8 C3 122.42(11)
O3 C9 C8 122.99(12)
O3 C9 C10 121.43(12)
C8 C9 C10 115.58(11)
C1 C10 C9 121.62(12)
C1 C10 C11 103.81(11)
C11 C10 C9 134.34(13)
O4 C11 C10 124.75(12)
N1 C11 O4 122.92(12)
N1 C11 C10 112.32(12)
O4 C12 H12A 110.0
O4 C12 H12B 110.0
O4 C12 C13 108.68(10)
H12A C12 H12B 108.3
C13 C12 H12A 110.0
C13 C12 H12B 110.0
C14 C13 C12 121.11(12)
C14 C13 C18 118.54(13)
C18 C13 C12 120.26(12)
C13 C14 H14 119.6
C13 C14 C15 120.83(13)
C15 C14 H14 119.6
C14 C15 H15 119.9
C14 C15 C16 120.27(13)
C16 C15 H15 119.9
C15 C16 H16 120.3
C17 C16 C15 119.45(13)
C17 C16 H16 120.3
C16 C17 H17 120.0
C16 C17 C18 119.99(13)
C18 C17 H17 120.0
C13 C18 H18 119.6
C17 C18 C13 120.90(13)
C17 C18 H18 119.6
N2 C19 H19A 109.5
N2 C19 H19B 109.5
N2 C19 H19C 109.5
H19A C19 H19B 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
N2 C20 H20A 109.5
N2 C20 H20B 109.5
N2 C20 H20C 109.5
H20A C20 H20B 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.4424(13)
O1 C1 1.3409(16)
O2 C7 1.3372(17)
O2 H2 0.96(2)
O3 C9 1.2629(16)
O4 C11 1.3339(15)
O4 C12 1.4593(15)
N1 C11 1.3097(17)
N2 C2 1.4695(16)
N2 C19 1.4619(16)
N2 C20 1.4587(16)
C1 C2 1.5006(18)
C1 C10 1.3547(19)
C2 H2A 1.0000
C2 C3 1.5583(17)
C3 H3 1.0000
C3 C4 1.5298(18)
C3 C8 1.5231(18)
C4 H4A 0.9900
C4 H4B 0.9900
C4 C5 1.5049(19)
C5 H5 0.9500
C5 C6 1.332(2)
C6 H6 0.9500
C6 C7 1.452(2)
C7 C8 1.3762(18)
C8 C9 1.4339(18)
C9 C10 1.4586(18)
C10 C11 1.4345(18)
C12 H12A 0.9900
C12 H12B 0.9900
C12 C13 1.4982(19)
C13 C14 1.3821(19)
C13 C18 1.3913(19)
C14 H14 0.9500
C14 C15 1.383(2)
C15 H15 0.9500
C15 C16 1.386(2)
C16 H16 0.9500
C16 C17 1.383(2)
C17 H17 0.9500
C17 C18 1.385(2)
C18 H18 0.9500
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
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
O2 H2 O3 0.96(2) 1.62(2) 2.5205(13) 153.7(18)
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
O1 N1 C11 O4 178.50(11)
O1 N1 C11 C10 -0.99(13)
O1 C1 C2 N2 -69.01(14)
O1 C1 C2 C3 164.22(10)
O1 C1 C10 C9 174.47(10)
O1 C1 C10 C11 -0.79(13)
O2 C7 C8 C3 175.39(11)
O2 C7 C8 C9 3.58(18)
O3 C9 C10 C1 -169.16(11)
O3 C9 C10 C11 4.4(2)
O4 C12 C13 C14 -106.43(14)
O4 C12 C13 C18 77.16(15)
N1 O1 C1 C2 172.96(10)
N1 O1 C1 C10 0.23(13)
N2 C2 C3 C4 35.12(14)
N2 C2 C3 C8 -92.03(13)
C1 O1 N1 C11 0.48(12)
C1 C2 C3 C4 160.61(10)
C1 C2 C3 C8 33.47(14)
C1 C10 C11 O4 -178.34(11)
C1 C10 C11 N1 1.14(14)
C2 C1 C10 C9 2.36(19)
C2 C1 C10 C11 -172.90(12)
C2 C3 C4 C5 -178.80(11)
C2 C3 C8 C7 162.65(11)
C2 C3 C8 C9 -25.85(16)
C3 C4 C5 C6 34.30(18)
C3 C8 C9 O3 -178.19(11)
C3 C8 C9 C10 2.36(16)
C4 C3 C8 C7 35.04(14)
C4 C3 C8 C9 -153.45(12)
C4 C5 C6 C7 -1.7(2)
C5 C6 C7 O2 165.97(13)
C5 C6 C7 C8 -15.6(2)
C6 C7 C8 C3 -3.00(17)
C6 C7 C8 C9 -174.80(12)
C7 C8 C9 O3 -6.75(18)
C7 C8 C9 C10 173.80(11)
C8 C3 C4 C5 -48.59(14)
C8 C9 C10 C1 10.30(17)
C8 C9 C10 C11 -176.14(13)
C9 C10 C11 O4 7.3(2)
C9 C10 C11 N1 -173.21(12)
C10 C1 C2 N2 102.38(15)
C10 C1 C2 C3 -24.39(17)
C11 O4 C12 C13 -165.96(11)
C12 O4 C11 N1 6.22(17)
C12 O4 C11 C10 -174.34(11)
C12 C13 C14 C15 -178.57(13)
C12 C13 C18 C17 177.98(13)
C13 C14 C15 C16 1.3(2)
C14 C13 C18 C17 1.5(2)
C14 C15 C16 C17 0.2(2)
C15 C16 C17 C18 -0.9(2)
C16 C17 C18 C13 0.0(2)
C18 C13 C14 C15 -2.1(2)
C19 N2 C2 C1 -44.39(14)
C19 N2 C2 C3 78.64(13)
C20 N2 C2 C1 83.13(13)
C20 N2 C2 C3 -153.85(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 49806448
