#------------------------------------------------------------------------------
#$Date: 2020-05-14 01:33:37 +0300 (Thu, 14 May 2020) $
#$Revision: 252028 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038358.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_4038358
loop_
_publ_author_name
'Higgins, Tyler'
'Winkler, Jeffrey D.'
_publ_section_title
;
 Synthesis and Applications of the C2-Symmetrical Diamine,
 2,7-diazabicyclo[4.4.1]undecane.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00829
_journal_year                    2020
_chemical_formula_moiety         'C16 H20 N4 O5, C6 H3 N3 O6'
_chemical_formula_sum            'C22 H23 N7 O11'
_chemical_formula_weight         561.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-06
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2017.05.11 svn.r3410 for OlexSys, GUI svn.r5338)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.886(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.7611(12)
_cell_length_b                   6.7132(4)
_cell_length_c                   21.4546(14)
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.46
_cell_measurement_theta_min      3.20
_cell_volume                     2420.4(3)
_computing_data_collection       'Bruker APEX3 v2016.1-0'
_computing_data_reduction        'Bruker SAINT v8.37A'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'CMOS area detector'
_diffrn_measurement_device_type  'Bruker D8QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            44391
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.459
_diffrn_reflns_theta_min         3.196
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.773
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0094(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0825P)²+3.1706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1561
_reflns_number_gt                3693
_reflns_number_total             4439
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00829_si_002.cif
_cod_data_source_block           2078
_cod_database_code               4038358
_shelx_shelxl_version_number     2014/7
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.79374(15) 1.3210(4) 0.52812(12) 0.0260(6) Uani 1 1 d . . . . .
H1a H 0.8066 1.4238 0.5001 0.035 Uiso 1 1 calc R . . . .
H1b H 0.8088 1.3741 0.5736 0.035 Uiso 1 1 calc R . . . .
C2 C 0.70500(15) 1.2827(4) 0.50340(12) 0.0277(6) Uani 1 1 d . . . . .
H2a H 0.6909 1.2222 0.4590 0.037 Uiso 1 1 calc R . . . .
H2b H 0.6771 1.4122 0.4988 0.037 Uiso 1 1 calc R . . . .
C3 C 0.67445(15) 1.1484(5) 0.54670(13) 0.0310(6) Uani 1 1 d . . . . .
H3a H 0.6182 1.1834 0.5398 0.041 Uiso 1 1 calc R . . . .
H3b H 0.7049 1.1779 0.5933 0.041 Uiso 1 1 calc R . . . .
C4 C 0.67907(14) 0.9246(4) 0.53584(12) 0.0256(6) Uani 1 1 d . . . . .
H4 H 0.6622 0.8555 0.5704 0.034 Uiso 1 1 calc R . . . .
C5 C 0.76198(15) 0.8433(4) 0.54022(12) 0.0259(6) Uani 1 1 d . . . . .
H5a H 0.7695 0.7147 0.5641 0.034 Uiso 1 1 calc R . . . .
H5b H 0.7616 0.8146 0.4949 0.034 Uiso 1 1 calc R . . . .
C6 C 0.83404(14) 0.9732(4) 0.57326(11) 0.0218(5) Uani 1 1 d . . . . .
H6 H 0.8293 1.0312 0.6148 0.029 Uiso 1 1 calc R . . . .
C7 C 0.91316(15) 0.8664(4) 0.58812(13) 0.0300(6) Uani 1 1 d . . . . .
H7a H 0.9136 0.7790 0.5511 0.040 Uiso 1 1 calc R . . . .
H7b H 0.9247 0.7853 0.6287 0.040 Uiso 1 1 calc R . . . .
C8 C 0.97270(15) 1.0356(5) 0.59723(13) 0.0316(6) Uani 1 1 d . . . . .
H8a H 0.9865 1.0927 0.6421 0.042 Uiso 1 1 calc R . . . .
H8b H 1.0220 0.9889 0.5898 0.042 Uiso 1 1 calc R . . . .
C9 C 0.93003(15) 1.1864(5) 0.54596(13) 0.0319(6) Uani 1 1 d . . . . .
H9a H 0.9475 1.1757 0.5067 0.042 Uiso 1 1 calc R . . . .
H9b H 0.9411 1.3231 0.5639 0.042 Uiso 1 1 calc R . . . .
C10 C 0.54950(14) 0.8008(4) 0.46520(11) 0.0204(5) Uani 1 1 d . . . . .
C11 C 0.49283(13) 0.7891(4) 0.39540(11) 0.0182(5) Uani 1 1 d . . . . .
C12 C 0.43924(13) 0.6316(4) 0.37784(12) 0.0211(5) Uani 1 1 d . . . . .
H12 H 0.4397 0.5291 0.4085 0.028 Uiso 1 1 calc R . . . .
C13 C 0.38528(13) 0.6274(4) 0.31474(12) 0.0216(5) Uani 1 1 d . . . . .
C14 C 0.38163(14) 0.7720(4) 0.26823(11) 0.0219(5) Uani 1 1 d . . . . .
H14 H 0.3440 0.7659 0.2251 0.029 Uiso 1 1 calc R . . . .
C15 C 0.43544(14) 0.9256(4) 0.28769(11) 0.0220(5) Uani 1 1 d . . . . .
C16 C 0.49109(14) 0.9382(4) 0.35005(11) 0.0220(5) Uani 1 1 d . . . . .
H16 H 0.5274 1.0466 0.3616 0.029 Uiso 1 1 calc R . . . .
N1 N 0.84176(11) 1.1390(3) 0.52799(9) 0.0216(5) Uani 1 1 d . . . . .
N2 N 0.62207(12) 0.8708(3) 0.47170(10) 0.0253(5) Uani 1 1 d . . . . .
H2 H 0.6361 0.8852 0.4362 0.034 Uiso 1 1 calc R . . . .
N3 N 0.32802(14) 0.4626(4) 0.29545(12) 0.0357(6) Uani 1 1 d . . . . .
N4 N 0.43504(15) 1.0808(4) 0.23930(11) 0.0356(6) Uani 1 1 d . . . . .
O1 O 0.52709(10) 0.7502(3) 0.51141(8) 0.0255(4) Uani 1 1 d . . . . .
O2 O 0.29648(13) 0.4284(4) 0.23659(10) 0.0459(6) Uani 1 1 d . . . . .
O3 O 0.31155(17) 0.3754(5) 0.33923(13) 0.0819(11) Uani 1 1 d . . . . .
O4 O 0.38565(14) 1.0689(4) 0.18468(10) 0.0487(6) Uani 1 1 d . . . . .
O5 O 0.48506(18) 1.2114(4) 0.25508(11) 0.0685(9) Uani 1 1 d . . . . .
C17 C 0.82182(13) 0.5171(3) 0.32778(11) 0.0173(5) Uani 1 1 d . . . . .
C18 C 0.75277(14) 0.5283(3) 0.34355(11) 0.0173(5) Uani 1 1 d . . . . .
H18 H 0.7532 0.5294 0.3880 0.023 Uiso 1 1 calc R . . . .
C19 C 0.68274(13) 0.5379(3) 0.29122(11) 0.0161(5) Uani 1 1 d . . . . .
C20 C 0.68057(13) 0.5370(3) 0.22625(11) 0.0163(5) Uani 1 1 d . . . . .
H20 H 0.6312 0.5467 0.1916 0.022 Uiso 1 1 calc R . . . .
C21 C 0.75137(13) 0.5218(3) 0.21218(11) 0.0154(5) Uani 1 1 d . . . . .
C22 C 0.82307(13) 0.5110(3) 0.26369(11) 0.0163(5) Uani 1 1 d . . . . .
H22 H 0.8720 0.4995 0.2550 0.022 Uiso 1 1 calc R . . . .
N5 N 0.89766(12) 0.5084(3) 0.38209(10) 0.0229(5) Uani 1 1 d . . . . .
N6 N 0.75080(14) 0.5145(3) 0.14126(11) 0.0302(5) Uani 1 1 d . . . . .
N7 N 0.60747(12) 0.5533(3) 0.30574(10) 0.0220(5) Uani 1 1 d . . . . .
O6 O 0.95650(11) 0.4556(3) 0.36884(10) 0.0387(5) Uani 1 1 d . . . . .
O7 O 0.89805(11) 0.5536(3) 0.43751(8) 0.0328(5) Uani 1 1 d . . . . .
O8 O 0.81416(10) 0.4669(3) 0.13229(8) 0.0254(4) Uani 1 1 d . . . . .
O9 O 0.68544(10) 0.5585(3) 0.09851(8) 0.0269(4) Uani 1 1 d . . . . .
O10 O 0.60765(11) 0.5020(3) 0.36056(9) 0.0317(5) Uani 1 1 d . . . . .
O11 O 0.54959(10) 0.6182(3) 0.26206(9) 0.0281(4) Uani 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 113.1(2) . . ?
C1 C2 C3 115.2(2) . . ?
C2 C3 C4 116.4(2) . . ?
C3 C4 C5 115.8(2) . . ?
N2 C4 C3 109.3(2) . . ?
N2 C4 C5 109.0(2) . . ?
C6 C5 C4 117.9(2) . . ?
C7 C6 C5 114.2(2) . . ?
N1 C6 C5 111.12(19) . . ?
N1 C6 C7 102.3(2) . . ?
C6 C7 C8 103.4(2) . . ?
C9 C8 C7 104.1(2) . . ?
C8 C9 N1 106.1(2) . . ?
N2 C10 C11 115.6(2) . . ?
O1 C10 C11 119.9(2) . . ?
O1 C10 N2 124.5(2) . . ?
C12 C11 C10 119.0(2) . . ?
C16 C11 C10 120.9(2) . . ?
C16 C11 C12 120.0(2) . . ?
C13 C12 C11 118.5(2) . . ?
C12 C13 N3 119.2(2) . . ?
C14 C13 C12 123.4(2) . . ?
C14 C13 N3 117.4(2) . . ?
C15 C14 C13 116.3(2) . . ?
C14 C15 C16 123.2(2) . . ?
C14 C15 N4 118.2(2) . . ?
C16 C15 N4 118.6(2) . . ?
C15 C16 C11 118.7(2) . . ?
C1 N1 C6 115.54(19) . . ?
C1 N1 C9 111.8(2) . . ?
C6 N1 C9 106.92(19) . . ?
C10 N2 C4 122.31(19) . . ?
O2 N3 C13 118.3(2) . . ?
O3 N3 C13 117.5(2) . . ?
O3 N3 O2 124.1(2) . . ?
O4 N4 C15 118.1(2) . . ?
O5 N4 C15 118.6(2) . . ?
O5 N4 O4 123.3(2) . . ?
C18 C17 C22 123.3(2) . . ?
C18 C17 N5 117.9(2) . . ?
C22 C17 N5 118.8(2) . . ?
C17 C18 C19 116.3(2) . . ?
C18 C19 C20 122.9(2) . . ?
C18 C19 N7 118.2(2) . . ?
C20 C19 N7 118.9(2) . . ?
C19 C20 C21 119.2(2) . . ?
C20 C21 C22 119.4(2) . . ?
C20 C21 N6 120.5(2) . . ?
C22 C21 N6 120.08(19) . . ?
C17 C22 C21 118.9(2) . . ?
O6 N5 C17 117.4(2) . . ?
O6 N5 O7 124.2(2) . . ?
O7 N5 C17 118.4(2) . . ?
O8 N6 C21 116.8(2) . . ?
O8 N6 O9 127.9(2) . . ?
O9 N6 C21 115.3(2) . . ?
O10 N7 C19 117.6(2) . . ?
O10 N7 O11 125.1(2) . . ?
O11 N7 C19 117.26(19) . . ?
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 1.513(4) . ?
C1 N1 1.490(3) . ?
C2 C3 1.515(4) . ?
C3 C4 1.526(4) . ?
C4 C5 1.545(3) . ?
C4 N2 1.465(3) . ?
C5 C6 1.521(4) . ?
C6 C7 1.517(3) . ?
C6 N1 1.512(3) . ?
C7 C8 1.521(4) . ?
C8 C9 1.506(4) . ?
C9 N1 1.522(3) . ?
C10 C11 1.512(3) . ?
C10 N2 1.336(3) . ?
C10 O1 1.229(3) . ?
C11 C12 1.391(3) . ?
C11 C16 1.389(3) . ?
C12 C13 1.383(3) . ?
C13 C14 1.378(4) . ?
C13 N3 1.469(3) . ?
C14 C15 1.376(4) . ?
C15 C16 1.385(3) . ?
C15 N4 1.469(3) . ?
N3 O2 1.226(3) . ?
N3 O3 1.220(3) . ?
N4 O4 1.218(3) . ?
N4 O5 1.216(3) . ?
C17 C18 1.376(3) . ?
C17 C22 1.383(3) . ?
C17 N5 1.469(3) . ?
C18 C19 1.381(3) . ?
C19 C20 1.382(3) . ?
C19 N7 1.471(3) . ?
C20 C21 1.389(3) . ?
C21 C22 1.392(3) . ?
C21 N6 1.519(3) . ?
N5 O6 1.221(3) . ?
N5 O7 1.225(3) . ?
N6 O8 1.243(3) . ?
N6 O9 1.260(3) . ?
N7 O10 1.224(3) . ?
N7 O11 1.225(3) . ?
