#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/25/4022566.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_4022566
loop_
_publ_author_name
'Nathaniel C. Lim'
'Martha D. Morton'
'Hilary A. Jenkins'
'Christian Brückner'
_publ_section_title
;
 Squaric Acid N-Hydroxylamides: Synthesis, Structure,
 and Properties of Vinylogous Hydroxamic Acid Analogues
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9233
_journal_page_last               9241
_journal_paper_doi               10.1021/jo035175g
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C14 H20 N2 O4'
_chemical_formula_weight         280.32
_chemical_melting_point          441.1(10)
_chemical_name_systematic
;
3-Morpholino-4-N-cyclohexylhydroxylaminocyclobut-3-ene-1,2-dione
;
_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                 96.336(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4038(12)
_cell_length_b                   8.6745(8)
_cell_length_c                   13.2282(12)
_cell_measurement_temperature    198(2)
_cell_volume                     1414.6(2)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_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      198(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9525
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3180
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0460
_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)+(0.0733P)²+0.0921P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1355
_reflns_number_gt                2336
_reflns_number_total             3180
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo035175gsi20030814_084753.cif
_cod_data_source_block           Lim_et_al._compound_6c
_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 

The following automatic conversions were performed:

'_chemical_melting_point' value '167-169 degC' was changed to
'441.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022566
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
C1 C 0.62235(11) 0.24697(16) 0.64684(9) 0.0376(3) Uani 1 1 d .
C2 C 0.66087(12) 0.36499(17) 0.57960(10) 0.0412(3) Uani 1 1 d .
O1 O 0.73734(10) 0.45287(14) 0.58325(8) 0.0564(3) Uani 1 1 d .
C3 C 0.56291(12) 0.33226(17) 0.50717(10) 0.0419(3) Uani 1 1 d .
O2 O 0.52972(9) 0.36951(15) 0.41939(7) 0.0545(3) Uani 1 1 d .
C4 C 0.52380(11) 0.22939(17) 0.58310(9) 0.0397(3) Uani 1 1 d .
N3 N 0.67026(10) 0.18866(13) 0.73360(8) 0.0403(3) Uani 1 1 d .
O5 O 0.63073(8) 0.04387(11) 0.76169(7) 0.0458(3) Uani 1 1 d .
H5A H 0.5961 0.0547 0.8123 0.069 Uiso 1 1 calc R
C5 C 0.78751(11) 0.20980(17) 0.76240(10) 0.0412(3) Uani 1 1 d .
H5B H 0.8065 0.3167 0.7423 0.049 Uiso 1 1 calc R
C6 C 0.81319(14) 0.1976(2) 0.87711(11) 0.0519(4) Uani 1 1 d .
H6A H 0.7731 0.2786 0.9102 0.062 Uiso 1 1 calc R
H6B H 0.7887 0.0962 0.9002 0.062 Uiso 1 1 calc R
C7 C 0.93377(16) 0.2156(2) 0.90907(14) 0.0705(5) Uani 1 1 d .
H7A H 0.9563 0.3219 0.8941 0.085 Uiso 1 1 calc R
H7B H 0.9487 0.1988 0.9833 0.085 Uiso 1 1 calc R
C8 C 0.99868(17) 0.1025(3) 0.85400(19) 0.0868(7) Uani 1 1 d .
H8A H 0.9807 -0.0039 0.8735 0.104 Uiso 1 1 calc R
H8B H 1.0770 0.1194 0.8742 0.104 Uiso 1 1 calc R
C9 C 0.97451(15) 0.1211(3) 0.73954(18) 0.0789(6) Uani 1 1 d .
H9A H 1.0168 0.0445 0.7049 0.095 Uiso 1 1 calc R
H9B H 0.9969 0.2252 0.7195 0.095 Uiso 1 1 calc R
C10 C 0.85399(13) 0.0989(2) 0.70602(13) 0.0555(4) Uani 1 1 d .
H10A H 0.8393 0.1170 0.6319 0.067 Uiso 1 1 calc R
H10B H 0.8329 -0.0085 0.7200 0.067 Uiso 1 1 calc R
N4 N 0.43021(11) 0.15623(18) 0.58507(9) 0.0549(4) Uani 1 1 d .
C11 C 0.35073(14) 0.1476(2) 0.49482(12) 0.0592(5) Uani 1 1 d .
H11A H 0.3456 0.0401 0.4697 0.071 Uiso 1 1 calc R
H11B H 0.3748 0.2133 0.4403 0.071 Uiso 1 1 calc R
C12 C 0.24203(16) 0.2002(2) 0.51937(15) 0.0684(5) Uani 1 1 d .
H12A H 0.2450 0.3118 0.5351 0.082 Uiso 1 1 calc R
H12B H 0.1881 0.1845 0.4593 0.082 Uiso 1 1 calc R
O6 O 0.20882(10) 0.11873(17) 0.60323(11) 0.0728(4) Uani 1 1 d .
C13 C 0.28289(16) 0.1450(2) 0.68984(14) 0.0687(5) Uani 1 1 d .
H13A H 0.2567 0.0934 0.7492 0.082 Uiso 1 1 calc R
H13B H 0.2872 0.2570 0.7041 0.082 Uiso 1 1 calc R
C14 C 0.39330(14) 0.0858(2) 0.67554(13) 0.0653(5) Uani 1 1 d .
H14A H 0.4446 0.1109 0.7360 0.078 Uiso 1 1 calc R
H14B H 0.3909 -0.0277 0.6677 0.078 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
N3 C1 C4 138.28(13)
N3 C1 C2 129.91(13)
C4 C1 C2 91.81(11)
O1 C2 C1 135.89(13)
O1 C2 C3 136.38(13)
C1 C2 C3 87.70(11)
O2 C3 C4 134.79(14)
O2 C3 C2 136.10(14)
C4 C3 C2 89.05(11)
N4 C4 C1 137.80(13)
N4 C4 C3 131.42(13)
C1 C4 C3 90.76(11)
C1 N3 O5 115.42(11)
C1 N3 C5 120.60(11)
O5 N3 C5 113.82(10)
N3 C5 C10 111.64(12)
N3 C5 C6 109.98(12)
C10 C5 C6 112.44(13)
C7 C6 C5 111.27(15)
C8 C7 C6 111.18(15)
C7 C8 C9 110.81(16)
C8 C9 C10 110.85(17)
C5 C10 C9 110.24(14)
C4 N4 C14 124.77(13)
C4 N4 C11 121.38(13)
C14 N4 C11 113.76(13)
N4 C11 C12 110.51(14)
O6 C12 C11 111.51(15)
C13 O6 C12 109.72(14)
O6 C13 C14 111.51(16)
N4 C14 C13 109.52(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N3 1.3325(16)
C1 C4 1.4145(19)
C1 C2 1.4702(19)
C2 O1 1.2137(18)
C2 C3 1.489(2)
C3 O2 1.2315(16)
C3 C4 1.4656(19)
C4 N4 1.326(2)
N3 O5 1.4129(15)
N3 C5 1.4736(18)
C5 C10 1.516(2)
C5 C6 1.5194(18)
C6 C7 1.517(2)
C7 C8 1.507(3)
C8 C9 1.519(3)
C9 C10 1.524(3)
N4 C14 1.462(2)
N4 C11 1.4639(19)
C11 C12 1.492(3)
C12 O6 1.414(2)
O6 C13 1.406(2)
C13 C14 1.494(3)
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
O5 H5A O2 0.84 1.84 2.6575(14) 165.3 4_566
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9555385
