#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:01:10 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301838 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/29/4322956.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_4322956
loop_
_publ_author_name
'Hazel-Ann Hosein'
'Lincoln A. Hall'
'Alan J. Lough'
'William Desmarais'
'Michael J. Vela'
'Bruce M. Foxman'
_publ_contact_author
;
Bruce M. Foxman
Department of Chemistry
Brandeis University - MS 015
Waltham, MA 02254-9110 USA
;
_publ_contact_author_email       ' foxman1@binah.cc.brandeis.edu  '
_publ_contact_author_fax         ' 1 617 736 2516 '
_publ_contact_author_phone       ' 1 617 736 2532 '
_publ_section_title
;
 Attempted Syntheses of Transition Metal and Lanthanide
 (Dialkylamino)squarates. The Hydrolysis Problem
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4184
_journal_page_last               4189
_journal_paper_doi               10.1021/ic9801490
_journal_volume                  37
_journal_year                    1998
_chemical_compound_source
;
?
;
_chemical_formula_moiety         ' C6 H7 O3 N1 '
_chemical_formula_sum            'C6 H7 N O3'
_chemical_formula_weight         141.13
_chemical_name_systematic        1-(dimethylamino)-2-hydroxycyclobutenedione
_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
_audit_creation_date             97-12-18
_audit_creation_method           CRYSTALS_ver_07-07-97
_cell_angle_alpha                90.
_cell_angle_beta                 95.121(12)
_cell_angle_gamma                90.
_cell_formula_units_Z            4.00
_cell_length_a                   5.0933(7)
_cell_length_b                   8.3314(6)
_cell_length_c                   15.087(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294
_cell_measurement_theta_max      46
_cell_measurement_theta_min      41
_cell_volume                     637.65(16)
_computing_cell_refinement       'CAD4-EXPRESS (Straver, 1992)'
_computing_data_collection       'CAD4-EXPRESS (Straver, 1992)'
_computing_data_reduction
;
MolEN (Fair, C. K., 1990)
;
_computing_molecular_graphics
;
 CAMERON (Watkin, Prout & Pearce,  1996)
;
_computing_publication_material
;
CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)
;
_computing_structure_refinement
;
CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge, 1996)
;
_computing_structure_solution    'SHELXS86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      294
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.01
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            1350
_diffrn_reflns_theta_max         74.30
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  7200s
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.98
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '\y scan,(North et al, 1968)'
_exptl_crystal_colour            ' yellow '
_exptl_crystal_density_diffrn    1.47
_exptl_crystal_density_meas      ?
_exptl_crystal_description       ' cube '
_exptl_crystal_F_000             297.04
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.25
_refine_ls_extinction_coef       29.3(26)
_refine_ls_extinction_method     'Larson 1970 Crystallographic Computing eq 22'
_refine_ls_goodness_of_fit_obs   1.0364
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1157
_refine_ls_R_factor_obs          0.0347
_refine_ls_shift/su_max          0.107539
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Chebychev polynomial with   3 parameters (Carruthers & Watkin, 1979)
 2.65 1.54 1.62
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0425
_reflns_limit_h_max              6
_reflns_limit_h_min              0
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -18
_reflns_number_observed          1157
_reflns_number_total             1299
_reflns_observed_criterion       >1.96\s(I)
_cod_data_source_file            ic9801490.cif
_cod_data_source_block           IC9801490-Structure_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Direct_Methods' was changed to
'direct'.

'_atom_sites_solution_hydrogens' value 'Geometric' was changed to
'geom'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_cell_volume        637.66
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        ' C6 H7 O3 N1 '
_cod_database_code               4322956
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2
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 0.0489(5) 0.0572(6) 0.0470(6) -0.0069(4) -0.0045(4) -0.0150(4)
O2 0.0585(6) 0.0592(6) 0.0429(5) -0.0014(4) 0.0149(4) -0.0231(4)
O3 0.0538(5) 0.0513(5) 0.0550(6) 0.0074(4) 0.0104(4) -0.0198(4)
C1 0.0328(5) 0.0295(5) 0.0386(6) -0.0009(4) 0.0055(4) -0.0013(4)
C2 0.0353(5) 0.0315(5) 0.0399(6) 0.0013(4) 0.0048(4) -0.0029(4)
C3 0.0361(5) 0.0351(6) 0.0380(6) -0.0026(5) 0.0022(4) -0.0029(4)
C4 0.0375(6) 0.0367(6) 0.0377(6) -0.0031(5) 0.0071(4) -0.0048(5)
C5 0.0402(7) 0.0469(7) 0.0561(8) -0.0072(6) 0.0017(6) -0.0127(6)
C6 0.0652(9) 0.0610(9) 0.0366(7) 0.0038(6) -0.0003(6) -0.0114(7)
N1 0.0381(5) 0.0377(5) 0.0379(5) -0.0012(4) 0.0015(4) -0.0060(4)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_thermal_displace_type
O1 0.1858(2) 0.12106(12) 0.39996(7) 0.0516 1.0000 Uani
O2 0.6637(2) 0.37349(12) 0.43603(6) 0.0529 1.0000 Uani
O3 0.1895(2) 0.06967(12) 0.61685(7) 0.0530 1.0000 Uani
C1 0.5371(2) 0.26084(13) 0.58009(8) 0.0335 1.0000 Uani
C2 0.3196(2) 0.15108(14) 0.56363(8) 0.0354 1.0000 Uani
C3 0.3168(2) 0.17444(14) 0.46984(8) 0.0365 1.0000 Uani
C4 0.5371(2) 0.28985(14) 0.48274(8) 0.0371 1.0000 Uani
C5 0.8835(3) 0.43296(18) 0.64435(11) 0.0479 1.0000 Uani
C6 0.6329(4) 0.2557(2) 0.7398(1) 0.0546 1.0000 Uani
N1 0.67691(19) 0.31267(12) 0.65064(7) 0.0380 1.0000 Uani
H1 -0.005(5) 0.024(4) 0.4003(19) 0.13(1) 1.0000 Uiso
H51 0.826(4) 0.533(3) 0.6696(13) 0.075(6) 1.0000 Uiso
H52 1.045(4) 0.394(2) 0.6745(15) 0.075(6) 1.0000 Uiso
H53 0.919(4) 0.451(2) 0.5837(14) 0.070(5) 1.0000 Uiso
H61 0.799(5) 0.223(3) 0.7695(17) 0.106(8) 1.0000 Uiso
H62 0.574(5) 0.345(3) 0.7768(18) 0.107(8) 1.0000 Uiso
H63 0.497(5) 0.167(3) 0.7359(16) 0.098(7) 1.0000 Uiso
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'O   ' 0.0470 0.0320 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B
'N   ' 0.0290 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 International_Tables_Vol_IV_Table_2.2B
'C   ' 0.0170 0.0090 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H   ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997
0.0030 International_Tables_Vol_IV_Table_2.2B
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 . O1 . H1 . 124.4(13) no
C2 . O3 . H1 2_556 129.2(13) no
C2 . C1 . C4 . 90.05(9) yes
C2 . C1 . N1 . 135.09(11) yes
C4 . C1 . N1 . 134.9(1) yes
O3 . C2 . C1 . 131.40(11) yes
O3 . C2 . C3 . 137.23(11) yes
C1 . C2 . C3 . 91.37(9) yes
O1 . C3 . C2 . 136.87(11) yes
O1 . C3 . C4 . 132.10(11) yes
C2 . C3 . C4 . 91.02(9) yes
O2 . C4 . C1 . 135.37(11) yes
O2 . C4 . C3 . 137.08(11) yes
C1 . C4 . C3 . 87.55(9) yes
N1 . C5 . H51 . 108.6(12) no
N1 . C5 . H52 . 109.4(12) no
H51 . C5 . H52 . 112.3(17) no
N1 . C5 . H53 . 111.4(12) no
H51 . C5 . H53 . 109.2(16) no
H52 . C5 . H53 . 106.0(17) no
N1 . C6 . H61 . 108.6(16) no
N1 . C6 . H62 . 110.8(16) no
H61 . C6 . H62 . 104.1(22) no
N1 . C6 . H63 . 110.2(14) no
H61 . C6 . H63 . 113.2(21) no
H62 . C6 . H63 . 109.9(22) no
C1 . N1 . C5 . 121.27(11) yes
C1 . N1 . C6 . 121.82(11) yes
C5 . N1 . C6 . 116.90(11) yes
O1 . H1 . O3 2_556 167.6(26) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C3 . 1.2762(15) yes
O1 . H1 . 1.27(3) no
O2 . C4 . 1.2160(15) yes
O3 . C2 . 1.2803(15) yes
O3 . H1 2_556 1.23(3) no
C1 . C2 . 1.4407(15) yes
C1 . C4 . 1.4885(15) yes
C1 . N1 . 1.3005(15) yes
C2 . C3 . 1.4272(16) yes
C3 . C4 . 1.4775(15) yes
C5 . N1 . 1.4623(16) yes
C5 . H51 . 0.98(2) no
C5 . H52 . 0.96(2) no
C5 . H53 . 0.96(2) no
C6 . N1 . 1.4623(17) yes
C6 . H61 . 0.96(3) no
C6 . H62 . 0.99(3) no
C6 . H63 . 1.01(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 558928
