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#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/25/4022565.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_4022565
loop_
_publ_author_name
'Nathaniel C. Lim'
'Martha D. Morton'
'Hilary A. Jenkins'
'Christian Br\"uckner'
_publ_contact_author_address
;   Department of Chemistry
     University of Connecticut
     Storrs, CT 06269-3060
;
_publ_contact_author_email       c.bruckner@uconn.edu
_publ_contact_author_fax         '860 486 2981'
_publ_contact_author_name        'Dr. Christian Bruckner'
_publ_contact_author_phone       '860 486 2743'
_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            'C8 H11 N O4'
_chemical_formula_weight         185.18
_chemical_melting_point          422.1(10)
_chemical_name_systematic
;
3-Methoxy-4-N-isopropylhydroxylaminocyclobut-3-ene-1,2-dione
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 113.915(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.730(16)
_cell_length_b                   4.577(2)
_cell_length_c                   13.538(7)
_cell_measurement_temperature    291(2)
_cell_volume                     1684.2(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4375
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.118
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0044(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0449
_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/[\s^2^(Fo^2^)+(0.0781P)^2^+0.1960P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1336
_reflns_number_gt                1164
_reflns_number_total             1743
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo035175gsi20030814_084736.cif
_cod_data_source_block           Lim_et_al._compound_5b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '148-150 degC' was changed to
'422.1(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      'C 2/c'
_cod_database_code               4022565
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.38622(5) 0.3065(3) 0.51082(10) 0.0421(4) Uani 1 1 d .
H1A H 0.4019 0.2702 0.5751 0.063 Uiso 1 1 calc R
O2 O 0.46329(5) 0.2597(3) 0.41941(11) 0.0495(4) Uani 1 1 d .
O3 O 0.43515(5) -0.1691(4) 0.21439(11) 0.0558(5) Uani 1 1 d .
O4 O 0.34679(6) -0.4139(3) 0.26619(12) 0.0579(5) Uani 1 1 d .
N1 N 0.37048(5) 0.0507(3) 0.45482(12) 0.0396(4) Uani 1 1 d .
C1 C 0.39018(7) -0.0185(4) 0.38955(14) 0.0376(5) Uani 1 1 d .
C2 C 0.42988(7) 0.0684(4) 0.37012(15) 0.0391(5) Uani 1 1 d .
C3 C 0.41885(7) -0.1218(4) 0.28142(15) 0.0428(5) Uani 1 1 d .
C4 C 0.37731(7) -0.2333(4) 0.30240(15) 0.0427(5) Uani 1 1 d .
C5 C 0.32297(7) -0.0577(4) 0.44339(16) 0.0434(5) Uani 1 1 d .
H5A H 0.3177 -0.2461 0.4060 0.052 Uiso 1 1 calc R
C6 C 0.28311(8) 0.1408(6) 0.3761(2) 0.0678(7) Uani 1 1 d .
H6A H 0.2845 0.1657 0.3070 0.102 Uiso 1 1 calc R
H6B H 0.2871 0.3269 0.4112 0.102 Uiso 1 1 calc R
H6C H 0.2519 0.0586 0.3662 0.102 Uiso 1 1 calc R
C7 C 0.32301(9) -0.1105(6) 0.55128(18) 0.0630(7) Uani 1 1 d .
H7A H 0.3495 -0.2402 0.5915 0.094 Uiso 1 1 calc R
H7B H 0.2923 -0.1971 0.5431 0.094 Uiso 1 1 calc R
H7C H 0.3273 0.0716 0.5892 0.094 Uiso 1 1 calc R
C8 C 0.50125(8) 0.2881(5) 0.38187(18) 0.0538(6) Uani 1 1 d .
H8A H 0.5241 0.4356 0.4232 0.081 Uiso 1 1 calc R
H8B H 0.4872 0.3430 0.3070 0.081 Uiso 1 1 calc R
H8C H 0.5181 0.1050 0.3900 0.081 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0499(8) 0.0339(7) 0.0401(7) -0.0059(6) 0.0158(6) -0.0061(6)
O2 0.0475(8) 0.0544(9) 0.0516(8) -0.0139(7) 0.0254(7) -0.0118(7)
O3 0.0507(9) 0.0744(11) 0.0431(8) -0.0122(7) 0.0198(7) 0.0011(8)
O4 0.0656(10) 0.0510(9) 0.0532(9) -0.0114(7) 0.0202(8) -0.0146(8)
N1 0.0436(10) 0.0328(9) 0.0426(9) -0.0064(7) 0.0177(7) -0.0074(7)
C1 0.0408(10) 0.0341(10) 0.0353(10) 0.0020(8) 0.0127(8) 0.0034(8)
C2 0.0391(10) 0.0373(10) 0.0379(10) -0.0001(8) 0.0125(8) 0.0029(9)
C3 0.0420(11) 0.0466(12) 0.0360(10) -0.0010(9) 0.0118(8) 0.0065(9)
C4 0.0467(12) 0.0374(11) 0.0377(10) -0.0008(8) 0.0106(9) 0.0013(10)
C5 0.0433(11) 0.0381(11) 0.0500(11) -0.0045(9) 0.0202(9) -0.0098(9)
C6 0.0441(13) 0.0643(16) 0.0820(17) 0.0088(13) 0.0123(12) -0.0048(12)
C7 0.0623(14) 0.0737(17) 0.0601(14) -0.0005(12) 0.0323(12) -0.0183(13)
C8 0.0448(12) 0.0648(15) 0.0559(13) -0.0062(11) 0.0246(10) -0.0068(11)
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
C2 O2 C8 115.76(16)
C1 N1 O1 116.32(15)
C1 N1 C5 122.78(16)
O1 N1 C5 116.89(15)
N1 C1 C2 137.02(18)
N1 C1 C4 132.74(18)
C2 C1 C4 90.24(16)
N1 C1 C3 177.69(16)
C2 C1 C3 43.98(11)
C4 C1 C3 46.32(11)
O2 C2 C1 129.91(17)
O2 C2 C3 136.44(18)
C1 C2 C3 93.65(16)
O2 C2 C4 176.26(16)
C1 C2 C4 46.78(11)
C3 C2 C4 46.93(12)
O3 C3 C2 136.4(2)
O3 C3 C4 135.08(19)
C2 C3 C4 88.47(16)
O3 C3 C1 176.54(18)
C2 C3 C1 42.37(11)
C4 C3 C1 46.16(11)
O4 C4 C1 135.5(2)
O4 C4 C3 136.98(19)
C1 C4 C3 87.52(16)
O4 C4 C2 177.67(17)
C1 C4 C2 42.98(11)
C3 C4 C2 44.60(11)
N1 C5 C6 111.08(17)
N1 C5 C7 109.93(17)
C6 C5 C7 112.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.370(2)
O2 C2 1.289(2)
O2 C8 1.419(2)
O3 C3 1.209(2)
O4 C4 1.178(2)
N1 C1 1.282(2)
N1 C5 1.445(2)
C1 C2 1.368(3)
C1 C4 1.463(3)
C1 C3 2.026(3)
C2 C3 1.410(3)
C2 C4 2.007(3)
C3 C4 1.467(3)
C5 C6 1.478(3)
C5 C7 1.480(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
O1 H1A O3 0.82 1.80 2.618(2) 176.7 6_556
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9461862
2 PubChem 11286875
