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#$Date: 2026-06-20 01:00:29 +0200 (Sat 20 de Jun de 2026) $
#$Revision: 306603 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/21/7252134.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_7252134
loop_
_publ_author_name
'Navasardyan, Mher A.'
'Chernyavskiy, Danila R.'
'Vener, Mikhail'
_publ_section_title
;
 Crystal structures of hydroxylamine and a 15-crown-5
 hydroxylaminosolvate: first observation of a cyclic hydroxylamine dimer
 (NH₂OH)₂
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D6CE00321D
_journal_year                    2026
_chemical_formula_moiety         'H3 N O'
_chemical_formula_sum            'H3 N O'
_chemical_formula_weight         33.03
_chemical_name_common            Aminol
_chemical_name_systematic        Hydroxylamine
_chemical_properties_physical    Air-sensitive,Hygroscopic
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2026-05-27 deposited with the CCDC.	2026-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.4508(3)
_cell_length_b                   4.8299(4)
_cell_length_c                   7.1955(6)
_cell_measurement_reflns_used    1777
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.5335
_cell_measurement_theta_min      5.084
_cell_volume                     154.68(2)
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2455
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.533
_diffrn_reflns_theta_min         5.084
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.7197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       needle
_exptl_crystal_F_000             72
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 151 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     31
_refine_ls_number_reflns         475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0250
_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)+(0.0291P)²+0.0098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0677
_reflns_Friedel_coverage         0.562
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                440
_reflns_number_total             475
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6ce00321d2.cif
_cod_data_source_block           150k
_cod_database_code               7252134
_shelx_shelxl_version_number     2019/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.999
_shelx_res_file
;
TITL m in P2(1)2(1)2(1)
    150k.res
    created by SHELXL-2019/3 at 01:54:24 on 26-May-2026
CELL 0.71073   4.4508   4.8299   7.1955  90.000  90.000  90.000
ZERR    4.00   0.0003   0.0004   0.0006   0.000   0.000   0.000
LATT -1
SYMM 0.5-X, -Y, 0.5+Z
SYMM -X, 0.5+Y, 0.5-Z
SYMM 0.5+X, 0.5-Y, -Z
SFAC N H O
UNIT 4 12 4
TEMP -123.150
SIZE .25 .01 .01

EQIV $1 -0.5+X, 0.5-Y, 1-Z
EQIV $2 -X, -0.5+Y, 0.5-Z
EQIV $3 0.5+X, 1.5-Y, 1-Z

HTAB O1 N1_$1
HTAB N1 O1_$2
HTAB N1 O1_$3

CONF H1 O1 N1 H2
CONF H1 O1 N1 H3

L.S. 10
BOND $H
FMAP 2
PLAN 10
ACTA

WGHT    0.029100    0.009800
FVAR       0.85588
N1    1    0.238286    0.440989    0.381465    11.00000    0.01497    0.02104 =
         0.02360    0.00012    0.00191    0.00154
O1    3   -0.060727    0.522136    0.436929    11.00000    0.01587    0.01798 =
         0.03827    0.00483    0.00418    0.00293
H1    2   -0.127434    0.386294    0.486713    11.00000    0.04008
H2    2    0.237297    0.415390    0.261005    11.00000    0.03799
H3    2    0.345613    0.589677    0.402867    11.00000    0.02249
HKLF 4




REM  m in P2(1)2(1)2(1)
REM wR2 = 0.0677, GooF = S = 1.121, Restrained GooF = 1.121 for all data
REM R1 = 0.0250 for 440 Fo > 4sig(Fo) and 0.0287 for all 475 data
REM 31 parameters refined using 0 restraints

END

WGHT      0.0292      0.0097

REM Highest difference peak  0.129,  deepest hole -0.157,  1-sigma level  0.036
Q1    1   0.2298  0.2993  0.4402  11.00000  0.05    0.13
Q2    1   0.3203  0.3358  0.4549  11.00000  0.05    0.12
Q3    1   0.1752  0.4067  0.5365  11.00000  0.05    0.11
Q4    1   0.2641  0.2783  0.3567  11.00000  0.05    0.11
Q5    1  -0.0972  0.5308  0.2942  11.00000  0.05    0.11
Q6    1  -0.0128  0.6817  0.5099  11.00000  0.05    0.11
Q7    1  -0.0498  0.6789  0.3888  11.00000  0.05    0.11
Q8    1  -0.2330  0.5939  0.3411  11.00000  0.05    0.11
Q9    1   0.2432  0.1191  0.2851  11.00000  0.05    0.10
Q10   1  -0.0135  0.5417  0.5615  11.00000  0.05    0.09
;
_shelx_res_checksum              24225
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_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
N1 N 0.2383(2) 0.4410(2) 0.38146(14) 0.0199(3) Uani 1 1 d . . . . .
O1 O -0.06073(19) 0.52214(18) 0.43693(13) 0.0240(3) Uani 1 1 d . . . . .
H1 H -0.127(5) 0.386(4) 0.487(3) 0.040(5) Uiso 1 1 d . . . . .
H2 H 0.237(4) 0.415(4) 0.261(3) 0.038(5) Uiso 1 1 d . . . . .
H3 H 0.346(4) 0.590(4) 0.403(2) 0.022(4) Uiso 1 1 d . . . . .
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
N1 0.0150(4) 0.0210(5) 0.0236(5) 0.0001(3) 0.0019(4) 0.0015(4)
O1 0.0159(4) 0.0180(4) 0.0383(5) 0.0048(4) 0.0042(4) 0.0029(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 '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'
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
O1 N1 H2 107.9(12) . . ?
O1 N1 H3 103.4(11) . . ?
H2 N1 H3 107.0(16) . . ?
N1 O1 H1 104.0(14) . . ?
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
N1 O1 1.4436(13) . ?
N1 H2 0.876(19) . ?
N1 H3 0.876(17) . ?
O1 H1 0.80(2) . ?
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
_geom_hbond_publ_flag
O1 H1 N1 0.80(2) 1.94(2) 2.7407(13) 176(2) 4_456 yes
N1 H2 O1 0.876(19) 2.501(19) 3.1569(15) 132.3(15) 3_545 yes
N1 H3 O1 0.876(17) 2.240(17) 3.0384(13) 151.4(14) 4_566 yes
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
H1 O1 N1 H2 105.7(19) . . . . ?
H1 O1 N1 H3 -141.2(18) . . . . ?
