#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:18:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178429 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/50/4025061.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_4025061
loop_
_publ_author_name
'Robin A. Weatherhead'
'Michael D. Carducci'
'Eugene A. Mash'
_publ_contact_author_address
;
     The University of Arizona
     Department of Chemistry and Biochemistry
     1306 E. University Boulevard
     Tucson, AZ 85721-0041
     USA
;
_publ_contact_author_email       emash@u.arizona.edu
_publ_contact_author_fax         520-621-8407
_publ_contact_author_name        'Professor Eugene A. Mash, Jr.'
_publ_contact_author_phone       520-621-6321
_publ_section_title
;
Synthesis of Conformationally Constrained Diaminodicarboxylic Acid
Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8773
_journal_page_last               8778
_journal_paper_doi               10.1021/jo901892d
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C34 H36 N2 O8'
_chemical_formula_sum            'C34 H36 N2 O8'
_chemical_formula_weight         600.65
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                98.037(2)
_cell_angle_beta                 106.442(2)
_cell_angle_gamma                100.826(2)
_cell_formula_units_Z            1
_cell_length_a                   7.7824(8)
_cell_length_b                   9.1091(9)
_cell_length_c                   11.1134(11)
_cell_measurement_reflns_used    2822
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.249
_cell_measurement_theta_min      2.3255
_cell_volume                     726.43(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'glass fiber'
_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  0.0688
_diffrn_reflns_av_sigmaI/netI    0.0875
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8288
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        .32
_diffrn_standards_interval_count 3636
_diffrn_standards_number         19
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.899488
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS (Bruker 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             318
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.867
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0418
_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)+(0.0254P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0864
_reflns_number_gt                1822
_reflns_number_total             2981
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo901892d_si_002_4.cif
_cod_data_source_block           25
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_sg_symbol_H-M      P-1
_cod_database_code               4025061
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N7 N 0.13545(19) 0.43550(16) 0.15052(12) 0.0234(4) Uani 1 1 d . . .
H7A H 0.0284 0.3689 0.1152 0.028 Uiso 1 1 calc R . .
O8 O 0.44473(16) 0.47606(14) 0.17870(11) 0.0281(3) Uani 1 1 d . . .
O9 O 0.23633(16) 0.28719(14) 0.02293(11) 0.0288(3) Uani 1 1 d . . .
O17 O 0.20602(16) 0.70701(13) 0.07283(11) 0.0269(3) Uani 1 1 d . . .
O18 O 0.24875(17) 0.84389(13) 0.26753(11) 0.0300(3) Uani 1 1 d . . .
C4 C 0.1818(2) 0.50184(18) 0.57107(15) 0.0206(4) Uani 1 1 d . . .
H4A H 0.3044 0.5029 0.6190 0.025 Uiso 1 1 calc R . .
C8 C 0.2857(2) 0.4070(2) 0.12228(16) 0.0223(4) Uani 1 1 d . . .
C2 C 0.2736(2) 0.5797(2) 0.37675(15) 0.0228(4) Uani 1 1 d . . .
H2A H 0.3538 0.5074 0.3753 0.027 Uiso 1 1 calc R . .
H2B H 0.3523 0.6837 0.4166 0.027 Uiso 1 1 calc R . .
C1 C 0.1481(2) 0.57483(19) 0.23871(16) 0.0219(4) Uani 1 1 d . . .
C5 C 0.0386(2) 0.46834(18) 0.62144(15) 0.0195(4) Uani 1 1 d . . .
C3 C 0.1420(2) 0.53376(18) 0.44909(15) 0.0194(4) Uani 1 1 d . . .
C6 C -0.0462(2) 0.5737(2) 0.25138(15) 0.0224(4) Uani 1 1 d . . .
H6A H -0.0728 0.6756 0.2494 0.027 Uiso 1 1 calc R . .
H6B H -0.1430 0.4977 0.1808 0.027 Uiso 1 1 calc R . .
C17 C 0.2063(2) 0.7130(2) 0.18207(17) 0.0227(4) Uani 1 1 d . . .
C11 C 0.3095(2) 0.1260(2) -0.13379(17) 0.0255(4) Uani 1 1 d . . .
C19 C 0.2884(3) 0.9831(2) 0.21962(17) 0.0321(5) Uani 1 1 d . . .
H19A H 0.1771 0.9916 0.1532 0.039 Uiso 1 1 calc R . .
H19B H 0.3882 0.9814 0.1809 0.039 Uiso 1 1 calc R . .
C20 C 0.3470(3) 1.1160(2) 0.33064(18) 0.0433(6) Uani 1 1 d . . .
H20A H 0.3747 1.2113 0.3008 0.065 Uiso 1 1 calc R . .
H20B H 0.4573 1.1066 0.3956 0.065 Uiso 1 1 calc R . .
H20C H 0.2471 1.1169 0.3680 0.065 Uiso 1 1 calc R . .
C16 C 0.3117(2) 0.1610(2) -0.25023(18) 0.0319(5) Uani 1 1 d . . .
H16A H 0.3663 0.2620 -0.2540 0.038 Uiso 1 1 calc R . .
C12 C 0.2322(3) -0.0223(2) -0.13132(19) 0.0390(5) Uani 1 1 d . . .
H12A H 0.2302 -0.0486 -0.0519 0.047 Uiso 1 1 calc R . .
C10 C 0.3892(3) 0.2463(2) -0.01350(17) 0.0338(5) Uani 1 1 d . . .
H10A H 0.4671 0.2070 0.0556 0.041 Uiso 1 1 calc R . .
H10B H 0.4667 0.3370 -0.0283 0.041 Uiso 1 1 calc R . .
C15 C 0.2350(3) 0.0498(3) -0.36182(19) 0.0402(5) Uani 1 1 d . . .
H15A H 0.2358 0.0754 -0.4417 0.048 Uiso 1 1 calc R . .
C14 C 0.1580(3) -0.0964(3) -0.3577(2) 0.0440(6) Uani 1 1 d . . .
H14A H 0.1050 -0.1722 -0.4343 0.053 Uiso 1 1 calc R . .
C13 C 0.1578(3) -0.1331(2) -0.2421(2) 0.0470(6) Uani 1 1 d . . .
H13A H 0.1063 -0.2349 -0.2384 0.056 Uiso 1 1 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N7 C1 121.09(14) . . ?
C8 N7 H7A 119.5 . . ?
C1 N7 H7A 119.5 . . ?
C8 O9 C10 114.75(13) . . ?
C17 O18 C19 115.76(13) . . ?
C5 C4 C3 118.54(15) . . ?
C5 C4 H4A 120.7 . . ?
C3 C4 H4A 120.7 . . ?
O8 C8 O9 123.53(16) . . ?
O8 C8 N7 125.78(16) . . ?
O9 C8 N7 110.67(15) . . ?
C3 C2 C1 104.96(13) . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.8 . . ?
N7 C1 C17 108.88(13) . . ?
N7 C1 C6 108.72(13) . . ?
C17 C1 C6 108.08(14) . . ?
N7 C1 C2 111.39(14) . . ?
C17 C1 C2 114.49(14) . . ?
C6 C1 C2 105.03(13) . . ?
C4 C5 C3 120.81(15) . 2_566 ?
C4 C5 C6 128.32(15) . 2_566 ?
C3 C5 C6 110.85(15) 2_566 2_566 ?
C4 C3 C5 120.65(15) . 2_566 ?
C4 C3 C2 128.36(15) . . ?
C5 C3 C2 110.94(15) 2_566 . ?
C5 C6 C1 105.28(13) 2_566 . ?
C5 C6 H6A 110.7 2_566 . ?
C1 C6 H6A 110.7 . . ?
C5 C6 H6B 110.7 2_566 . ?
C1 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
O17 C17 O18 123.51(16) . . ?
O17 C17 C1 125.05(16) . . ?
O18 C17 C1 111.36(14) . . ?
C12 C11 C16 118.32(17) . . ?
C12 C11 C10 121.08(17) . . ?
C16 C11 C10 120.60(17) . . ?
O18 C19 C20 107.91(14) . . ?
O18 C19 H19A 110.1 . . ?
C20 C19 H19A 110.1 . . ?
O18 C19 H19B 110.1 . . ?
C20 C19 H19B 110.1 . . ?
H19A C19 H19B 108.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C11 C16 C15 120.46(18) . . ?
C11 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?
C13 C12 C11 121.16(19) . . ?
C13 C12 H12A 119.4 . . ?
C11 C12 H12A 119.4 . . ?
O9 C10 C11 107.67(14) . . ?
O9 C10 H10A 110.2 . . ?
C11 C10 H10A 110.2 . . ?
O9 C10 H10B 110.2 . . ?
C11 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C14 C15 C16 120.41(19) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C15 C14 C13 119.62(19) . . ?
C15 C14 H14A 120.2 . . ?
C13 C14 H14A 120.2 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
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
N7 C8 1.353(2) . ?
N7 C1 1.460(2) . ?
N7 H7A 0.8800 . ?
O8 C8 1.2161(19) . ?
O9 C8 1.3504(19) . ?
O9 C10 1.454(2) . ?
O17 C17 1.2070(19) . ?
O18 C17 1.3379(19) . ?
O18 C19 1.456(2) . ?
C4 C5 1.386(2) . ?
C4 C3 1.387(2) . ?
C4 H4A 0.9500 . ?
C2 C3 1.507(2) . ?
C2 C1 1.558(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C1 C17 1.535(2) . ?
C1 C6 1.556(2) . ?
C5 C3 1.397(2) 2_566 ?
C5 C6 1.503(2) 2_566 ?
C3 C5 1.397(2) 2_566 ?
C6 C5 1.503(2) 2_566 ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C11 C12 1.379(3) . ?
C11 C16 1.379(2) . ?
C11 C10 1.496(2) . ?
C19 C20 1.501(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C16 C15 1.387(2) . ?
C16 H16A 0.9500 . ?
C12 C13 1.378(3) . ?
C12 H12A 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C15 C14 1.367(3) . ?
C15 H15A 0.9500 . ?
C14 C13 1.372(3) . ?
C14 H14A 0.9500 . ?
C13 H13A 0.9500 . ?
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
N7 H7A O17 0.88 2.27 2.9963(17) 140.3 2_565
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
C10 O9 C8 O8 -0.5(2) . . . . ?
C10 O9 C8 N7 -179.18(14) . . . . ?
C1 N7 C8 O8 12.3(3) . . . . ?
C1 N7 C8 O9 -169.12(13) . . . . ?
C8 N7 C1 C17 62.60(19) . . . . ?
C8 N7 C1 C6 -179.86(14) . . . . ?
C8 N7 C1 C2 -64.59(19) . . . . ?
C3 C2 C1 N7 -101.00(15) . . . . ?
C3 C2 C1 C17 134.91(14) . . . . ?
C3 C2 C1 C6 16.52(18) . . . . ?
C3 C4 C5 C3 0.2(3) . . . 2_566 ?
C3 C4 C5 C6 178.18(16) . . . 2_566 ?
C5 C4 C3 C5 -0.2(3) . . . 2_566 ?
C5 C4 C3 C2 177.07(16) . . . . ?
C1 C2 C3 C4 171.36(16) . . . . ?
C1 C2 C3 C5 -11.17(19) . . . 2_566 ?
N7 C1 C6 C5 103.19(15) . . . 2_566 ?
C17 C1 C6 C5 -138.76(14) . . . 2_566 ?
C2 C1 C6 C5 -16.13(17) . . . 2_566 ?
C19 O18 C17 O17 2.5(2) . . . . ?
C19 O18 C17 C1 -174.21(14) . . . . ?
N7 C1 C17 O17 13.3(2) . . . . ?
C6 C1 C17 O17 -104.60(19) . . . . ?
C2 C1 C17 O17 138.75(17) . . . . ?
N7 C1 C17 O18 -170.00(13) . . . . ?
C6 C1 C17 O18 72.06(16) . . . . ?
C2 C1 C17 O18 -44.59(19) . . . . ?
C17 O18 C19 C20 -175.64(15) . . . . ?
C12 C11 C16 C15 1.1(3) . . . . ?
C10 C11 C16 C15 -178.89(17) . . . . ?
C16 C11 C12 C13 -0.4(3) . . . . ?
C10 C11 C12 C13 179.61(18) . . . . ?
C8 O9 C10 C11 -173.01(15) . . . . ?
C12 C11 C10 O9 -74.7(2) . . . . ?
C16 C11 C10 O9 105.31(19) . . . . ?
C11 C16 C15 C14 -0.8(3) . . . . ?
C16 C15 C14 C13 -0.3(3) . . . . ?
C15 C14 C13 C12 1.0(3) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
