#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:08:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180289 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/03/7150320.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_7150320
loop_
_publ_author_name
'Adams, Luke A.'
'Charmant, Jonathan P. H.'
'Cox, Russell J.'
'Walter, Magnus'
'Whittingham, William G.'
_publ_section_title
;
 Efficient synthesis of protected cyclopropyl beta-aspartylphosphates.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              542
_journal_page_last               553
_journal_paper_doi               10.1039/b311322a
_journal_volume                  2
_journal_year                    2004
_chemical_formula_moiety         'C23 H25 N O4, C H Cl3'
_chemical_formula_sum            'C24 H26 Cl3 N O4'
_chemical_formula_weight         498.81
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.042(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.425(3)
_cell_length_b                   18.223(5)
_cell_length_c                   11.601(2)
_cell_measurement_reflns_used    820
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.7
_cell_measurement_theta_min      2.9
_cell_volume                     2559.0(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Frames, each covering 0.3 ° in ω'
_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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12277
_diffrn_reflns_theta_full        24.01
_diffrn_reflns_theta_max         24.01
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.387
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.420
_refine_diff_density_min         -1.004
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0726
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1057P)²+4.7009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1946
_refine_ls_wR_factor_ref         0.2173
_reflns_number_gt                2905
_reflns_number_total             4000
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            b311322a.txt
_cod_data_source_block           laa2a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        2558.9(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7150320
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0771(3) 0.4041(2) -0.0109(3) 0.0321(9) Uani 1 1 d . . .
H1 H 0.1124 0.4371 0.0493 0.039 Uiso 1 1 calc R . .
C2 C 0.0324(3) 0.4308(2) -0.1231(3) 0.0380(9) Uani 1 1 d . . .
H2A H 0.0375 0.4816 -0.1394 0.046 Uiso 1 1 calc R . .
C3 C -0.0197(3) 0.3837(2) -0.2116(3) 0.0382(9) Uani 1 1 d . . .
H3 H -0.0492 0.4018 -0.2891 0.046 Uiso 1 1 calc R . .
C4 C -0.0286(3) 0.3101(2) -0.1864(3) 0.0374(9) Uani 1 1 d . . .
H4 H -0.0655 0.2777 -0.2466 0.045 Uiso 1 1 calc R . .
C5 C 0.0162(3) 0.2832(2) -0.0735(3) 0.0311(8) Uani 1 1 d . . .
H5 H 0.0090 0.2326 -0.0569 0.037 Uiso 1 1 calc R . .
C6 C 0.0716(3) 0.33013(19) 0.0156(3) 0.0272(8) Uani 1 1 d . . .
C7 C 0.1283(3) 0.30168(19) 0.1345(3) 0.0278(8) Uani 1 1 d . . .
C8 C 0.1290(3) 0.35056(19) 0.2381(3) 0.0301(8) Uani 1 1 d . . .
C9 C 0.2281(4) 0.3700(2) 0.3159(3) 0.0391(10) Uani 1 1 d . . .
H9 H 0.2960 0.3507 0.3045 0.047 Uiso 1 1 calc R . .
C10 C 0.2280(4) 0.4175(2) 0.4103(4) 0.0518(12) Uani 1 1 d . . .
H10 H 0.2956 0.4308 0.4626 0.062 Uiso 1 1 calc R . .
C11 C 0.1302(5) 0.4450(2) 0.4272(4) 0.0569(13) Uani 1 1 d . . .
H11 H 0.1304 0.4772 0.4917 0.068 Uiso 1 1 calc R . .
C12 C 0.0315(4) 0.4266(2) 0.3519(4) 0.0519(12) Uani 1 1 d . . .
H12 H -0.0359 0.4457 0.3649 0.062 Uiso 1 1 calc R . .
C13 C 0.0306(4) 0.3802(2) 0.2568(4) 0.0388(9) Uani 1 1 d . . .
H13 H -0.0375 0.3684 0.2041 0.047 Uiso 1 1 calc R . .
C14 C 0.1794(3) 0.2367(2) 0.1442(3) 0.0299(8) Uani 1 1 d . . .
H14 H 0.1787 0.2110 0.0728 0.036 Uiso 1 1 calc R . .
C15 C 0.2372(3) 0.2007(2) 0.2562(3) 0.0304(8) Uani 1 1 d . . .
H15 H 0.2062 0.2118 0.3267 0.036 Uiso 1 1 calc R . .
C16 C 0.2833(3) 0.1251(2) 0.2534(3) 0.0325(9) Uani 1 1 d . . .
H16A H 0.2758 0.1014 0.1751 0.039 Uiso 1 1 calc R . .
H16B H 0.2771 0.0911 0.3182 0.039 Uiso 1 1 calc R . .
C17 C 0.3629(3) 0.18816(19) 0.2831(3) 0.0276(8) Uani 1 1 d . . .
C18 C 0.4195(3) 0.2137(2) 0.1893(3) 0.0286(8) Uani 1 1 d . . .
C19 C 0.5138(3) 0.1632(2) 0.4545(3) 0.0317(9) Uani 1 1 d . . .
C20 C 0.6506(3) 0.0754(2) 0.4135(3) 0.0380(9) Uani 1 1 d . . .
C21 C 0.6581(4) 0.0275(3) 0.5221(5) 0.0643(15) Uani 1 1 d . . .
H21A H 0.6478 0.0579 0.5885 0.096 Uiso 1 1 calc R . .
H21B H 0.7308 0.0040 0.5425 0.096 Uiso 1 1 calc R . .
H21C H 0.6005 -0.0102 0.5053 0.096 Uiso 1 1 calc R . .
C22 C 0.7418(4) 0.1317(3) 0.4313(5) 0.0609(14) Uani 1 1 d . . .
H22A H 0.7288 0.1653 0.3637 0.091 Uiso 1 1 calc R . .
H22B H 0.8129 0.1068 0.4378 0.091 Uiso 1 1 calc R . .
H22C H 0.7429 0.1594 0.5039 0.091 Uiso 1 1 calc R . .
C23 C 0.6480(5) 0.0297(3) 0.3041(5) 0.0750(17) Uani 1 1 d . . .
H23A H 0.5863 -0.0050 0.2931 0.112 Uiso 1 1 calc R . .
H23B H 0.7175 0.0026 0.3134 0.112 Uiso 1 1 calc R . .
H23C H 0.6384 0.0620 0.2349 0.112 Uiso 1 1 calc R . .
N1 N 0.4206(2) 0.19893(17) 0.4043(2) 0.0307(7) Uani 1 1 d . . .
H1A H 0.3934 0.2305 0.4475 0.037 Uiso 1 1 calc R . .
O1 O 0.3913(2) 0.19442(15) 0.0870(2) 0.0369(7) Uani 1 1 d . . .
O2 O 0.4986(2) 0.26238(17) 0.2279(2) 0.0409(7) Uani 1 1 d . . .
O3 O 0.5668(2) 0.17537(17) 0.5554(2) 0.0463(8) Uani 1 1 d . . .
O4 O 0.5418(2) 0.11333(14) 0.3826(2) 0.0366(7) Uani 1 1 d . . .
C24 C -0.3432(5) 0.3505(3) 0.4305(5) 0.0688(15) Uani 1 1 d . . .
H24 H -0.3918 0.3066 0.4088 0.083 Uiso 1 1 calc R . .
Cl1 Cl -0.2541(2) 0.35281(19) 0.3372(2) 0.1492(11) Uani 1 1 d . . .
Cl2 Cl -0.4269(2) 0.42523(13) 0.4228(3) 0.1573(12) Uani 1 1 d . . .
Cl3 Cl -0.2678(2) 0.33770(13) 0.57467(16) 0.1242(8) Uani 1 1 d . . .
H2 H 0.522(7) 0.278(5) 0.179(7) 0.149 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 121.3(4) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C3 C2 C1 120.2(4) . . ?
C3 C2 H2A 119.9 . . ?
C1 C2 H2A 119.9 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.2(3) . . ?
C1 C6 C7 120.3(3) . . ?
C5 C6 C7 121.4(3) . . ?
C14 C7 C6 120.2(3) . . ?
C14 C7 C8 122.9(3) . . ?
C6 C7 C8 116.9(3) . . ?
C13 C8 C9 118.4(4) . . ?
C13 C8 C7 120.6(3) . . ?
C9 C8 C7 121.0(3) . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 119.9(5) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.8(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 120.0(4) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 120.6(4) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C7 C14 C15 126.3(3) . . ?
C7 C14 H14 116.9 . . ?
C15 C14 H14 116.9 . . ?
C14 C15 C16 119.9(3) . . ?
C14 C15 C17 120.7(3) . . ?
C16 C15 C17 59.5(2) . . ?
C14 C15 H15 115.2 . . ?
C16 C15 H15 115.2 . . ?
C17 C15 H15 115.2 . . ?
C15 C16 C17 61.7(2) . . ?
C15 C16 H16A 117.6 . . ?
C17 C16 H16A 117.6 . . ?
C15 C16 H16B 117.6 . . ?
C17 C16 H16B 117.6 . . ?
H16A C16 H16B 114.7 . . ?
N1 C17 C18 117.1(3) . . ?
N1 C17 C16 119.0(3) . . ?
C18 C17 C16 117.6(3) . . ?
N1 C17 C15 115.9(3) . . ?
C18 C17 C15 115.4(3) . . ?
C16 C17 C15 58.8(2) . . ?
O1 C18 O2 123.7(3) . . ?
O1 C18 C17 122.8(3) . . ?
O2 C18 C17 113.4(3) . . ?
O3 C19 O4 124.1(3) . . ?
O3 C19 N1 123.5(3) . . ?
O4 C19 N1 112.4(3) . . ?
O4 C20 C22 109.3(3) . . ?
O4 C20 C23 102.0(3) . . ?
C22 C20 C23 111.3(4) . . ?
O4 C20 C21 110.4(3) . . ?
C22 C20 C21 112.0(4) . . ?
C23 C20 C21 111.5(4) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 N1 C17 123.3(3) . . ?
C19 N1 H1A 118.4 . . ?
C17 N1 H1A 118.4 . . ?
C18 O2 H2 113(7) . . ?
C19 O4 C20 121.2(3) . . ?
Cl2 C24 Cl1 114.9(4) . . ?
Cl2 C24 Cl3 110.4(3) . . ?
Cl1 C24 Cl3 109.0(3) . . ?
Cl2 C24 H24 107.4 . . ?
Cl1 C24 H24 107.4 . . ?
Cl3 C24 H24 107.4 . . ?
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 1.383(5) . ?
C1 C6 1.388(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.383(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.493(5) . ?
C7 C14 1.337(5) . ?
C7 C8 1.495(5) . ?
C8 C13 1.397(6) . ?
C8 C9 1.398(6) . ?
C9 C10 1.396(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.369(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.487(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.495(5) . ?
C15 C17 1.539(5) . ?
C15 H15 1.0000 . ?
C16 C17 1.505(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N1 1.440(5) . ?
C17 C18 1.497(5) . ?
C18 O1 1.211(4) . ?
C18 O2 1.324(5) . ?
C19 O3 1.226(4) . ?
C19 O4 1.332(4) . ?
C19 N1 1.341(5) . ?
C20 O4 1.488(4) . ?
C20 C22 1.507(6) . ?
C20 C23 1.511(6) . ?
C20 C21 1.517(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N1 H1A 0.8800 . ?
O2 H2 0.75(8) . ?
C24 Cl2 1.703(6) . ?
C24 Cl1 1.714(6) . ?
C24 Cl3 1.738(5) . ?
C24 H24 1.0000 . ?
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
C6 C1 C2 C3 0.4(6) . . . . ?
C1 C2 C3 C4 1.2(6) . . . . ?
C2 C3 C4 C5 -1.1(6) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C2 C1 C6 C5 -2.0(5) . . . . ?
C2 C1 C6 C7 175.0(3) . . . . ?
C4 C5 C6 C1 2.2(5) . . . . ?
C4 C5 C6 C7 -174.9(3) . . . . ?
C1 C6 C7 C14 -141.0(4) . . . . ?
C5 C6 C7 C14 36.0(5) . . . . ?
C1 C6 C7 C8 36.3(5) . . . . ?
C5 C6 C7 C8 -146.7(3) . . . . ?
C14 C7 C8 C13 -130.3(4) . . . . ?
C6 C7 C8 C13 52.5(5) . . . . ?
C14 C7 C8 C9 52.1(5) . . . . ?
C6 C7 C8 C9 -125.1(4) . . . . ?
C13 C8 C9 C10 0.4(5) . . . . ?
C7 C8 C9 C10 178.0(3) . . . . ?
C8 C9 C10 C11 0.4(6) . . . . ?
C9 C10 C11 C12 -0.3(7) . . . . ?
C10 C11 C12 C13 -0.6(7) . . . . ?
C11 C12 C13 C8 1.3(6) . . . . ?
C9 C8 C13 C12 -1.2(5) . . . . ?
C7 C8 C13 C12 -178.8(3) . . . . ?
C6 C7 C14 C15 -178.7(3) . . . . ?
C8 C7 C14 C15 4.2(6) . . . . ?
C7 C14 C15 C16 175.4(3) . . . . ?
C7 C14 C15 C17 -114.5(4) . . . . ?
C14 C15 C16 C17 110.1(4) . . . . ?
C15 C16 C17 N1 104.4(3) . . . . ?
C15 C16 C17 C18 -104.4(3) . . . . ?
C14 C15 C17 N1 141.5(3) . . . . ?
C16 C15 C17 N1 -109.6(3) . . . . ?
C14 C15 C17 C18 -0.6(5) . . . . ?
C16 C15 C17 C18 108.3(3) . . . . ?
C14 C15 C17 C16 -108.9(4) . . . . ?
N1 C17 C18 O1 164.1(3) . . . . ?
C16 C17 C18 O1 12.2(5) . . . . ?
C15 C17 C18 O1 -54.3(5) . . . . ?
N1 C17 C18 O2 -19.6(4) . . . . ?
C16 C17 C18 O2 -171.4(3) . . . . ?
C15 C17 C18 O2 122.1(3) . . . . ?
O3 C19 N1 C17 175.5(4) . . . . ?
O4 C19 N1 C17 -4.5(5) . . . . ?
C18 C17 N1 C19 -67.6(5) . . . . ?
C16 C17 N1 C19 83.8(4) . . . . ?
C15 C17 N1 C19 150.9(3) . . . . ?
O3 C19 O4 C20 -9.2(6) . . . . ?
N1 C19 O4 C20 170.8(3) . . . . ?
C22 C20 O4 C19 -58.1(5) . . . . ?
C23 C20 O4 C19 -176.0(4) . . . . ?
C21 C20 O4 C19 65.5(5) . . . . ?
