#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/79/2237927.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2237927
loop_
_publ_author_name
'Gaumet, V.'
'Denis, C.'
'Leal, F.'
'Madesclaire, M.'
'Zaitsev, V. P.'
_publ_section_title
;
 [(2R,3R)-3-(4-Nitrophenyl)aziridin-2-yl]methanol
 monohydrate
;
_journal_coeditor_code           KP2453
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o927
_journal_paper_doi               10.1107/S1600536813013391
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C9 H10 N2 O3, H2 O'
_chemical_formula_moiety         'C9 H10 N2 O3, H2 O'
_chemical_formula_sum            'C9 H12 N2 O4'
_chemical_formula_weight         212.21
_chemical_melting_point          379
_chemical_name_systematic
;
[(2R,3R)-3-(4-Nitrophenyl)aziridin-2-yl]methanol monohydrate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 94.303(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.3064(2)
_cell_length_b                   5.4695(2)
_cell_length_c                   14.6481(5)
_cell_measurement_reflns_used    98
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      5.10
_cell_volume                     503.83(3)
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5357
_diffrn_reflns_theta_full        29.12
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         3.98
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.680
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.189
_refine_ls_abs_structure_details
;
The absolute configuration was assigned to agree with that of its precusor
at the chiral center C2.
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2383
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0349
_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)+(0.0435P)²+0.0307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0797
_refine_ls_wR_factor_ref         0.0860
_reflns_number_gt                2031
_reflns_number_total             2383
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            kp2453.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2237927
_cod_database_fobs_code          2237927
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N1 0.6266(2) 0.3667(2) 0.33556(10) 0.0457(3) Uani d . 1 1
H H1 0.573(3) 0.212(5) 0.3340(14) 0.063(6) Uiso d . 1 1
C C2 0.4417(2) 0.5260(3) 0.34835(10) 0.0394(3) Uani d . 1 1
H H2 0.3069 0.4423 0.3563 0.047 Uiso calc R 1 1
C C3 0.5261(2) 0.5024(3) 0.25666(9) 0.0394(3) Uani d . 1 1
H H3 0.4388 0.4018 0.2131 0.047 Uiso calc R 1 1
C C4 0.4863(3) 0.7468(3) 0.40646(10) 0.0397(3) Uani d . 1 1
H H4A 0.4745 0.7051 0.4702 0.048 Uiso calc R 1 1
H H4B 0.6303 0.8024 0.3998 0.048 Uiso calc R 1 1
O O5 0.3410(2) 0.9368(2) 0.38063(8) 0.0489(3) Uani d . 1 1
H H5 0.256(3) 0.927(4) 0.4181(12) 0.051(5) Uiso d . 1 1
C C6 0.6449(2) 0.7016(3) 0.21394(9) 0.0357(3) Uani d . 1 1
C C7 0.8526(2) 0.7649(3) 0.24213(10) 0.0426(4) Uani d . 1 1
H H7 0.9250 0.6782 0.2894 0.051 Uiso calc R 1 1
C C8 0.9530(2) 0.9552(3) 0.20089(9) 0.0422(4) Uani d . 1 1
H H8 1.0915 0.9990 0.2205 0.051 Uiso calc R 1 1
C C9 0.8439(2) 1.0790(3) 0.13006(9) 0.0361(3) Uani d . 1 1
C C10 0.6386(2) 1.0188(3) 0.09979(9) 0.0408(4) Uani d . 1 1
H H10 0.5676 1.1043 0.0519 0.049 Uiso calc R 1 1
C C11 0.5409(2) 0.8300(3) 0.14185(9) 0.0401(4) Uani d . 1 1
H H11 0.4025 0.7871 0.1218 0.048 Uiso calc R 1 1
N N12 0.9485(2) 1.2823(3) 0.08617(8) 0.0438(3) Uani d . 1 1
O O13 1.13280(19) 1.3298(3) 0.11207(9) 0.0642(4) Uani d . 1 1
O O14 0.8479(2) 1.3952(3) 0.02591(8) 0.0611(4) Uani d . 1 1
O O1W 0.9400(2) 0.4031(3) 0.47803(9) 0.0568(3) Uani d D 1 1
H H1W 0.856(4) 0.392(5) 0.4262(14) 0.089(8) Uiso d D 1 1
H H2W 0.990(4) 0.252(4) 0.491(2) 0.092(8) Uiso d D 1 1
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_publ_flag
C3 N1 C2 60.44(10) n
C3 N1 H1 108.1(13) n
C2 N1 H1 104.8(14) n
N1 C2 C3 59.67(10) n
N1 C2 C4 115.62(13) n
C3 C2 C4 121.37(12) n
N1 C2 H2 116.0 n
C3 C2 H2 116.0 n
C4 C2 H2 116.0 n
N1 C3 C6 119.88(13) n
N1 C3 C2 59.88(10) n
C6 C3 C2 122.85(12) n
N1 C3 H3 114.5 n
C6 C3 H3 114.5 n
C2 C3 H3 114.5 n
O5 C4 C2 110.52(12) n
O5 C4 H4A 109.5 n
C2 C4 H4A 109.5 n
O5 C4 H4B 109.5 n
C2 C4 H4B 109.5 n
H4A C4 H4B 108.1 n
C4 O5 H5 102.8(15) n
C7 C6 C11 118.73(14) n
C7 C6 C3 123.49(13) n
C11 C6 C3 117.77(13) n
C8 C7 C6 120.79(13) n
C8 C7 H7 119.6 n
C6 C7 H7 119.6 n
C9 C8 C7 118.67(13) n
C9 C8 H8 120.7 n
C7 C8 H8 120.7 n
C10 C9 C8 121.95(14) n
C10 C9 N12 118.91(13) n
C8 C9 N12 119.14(13) n
C11 C10 C9 118.58(13) n
C11 C10 H10 120.7 n
C9 C10 H10 120.7 n
C10 C11 C6 121.27(13) n
C10 C11 H11 119.4 n
C6 C11 H11 119.4 n
O14 N12 O13 123.31(15) n
O14 N12 C9 118.43(13) n
O13 N12 C9 118.25(13) n
H1W O1W H2W 107(2) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C3 1.476(2) n
N1 C2 1.479(2) n
N1 H1 0.91(2) n
C2 C3 1.487(2) n
C2 C4 1.492(2) n
C2 H2 0.9800 n
C3 C6 1.487(2) n
C3 H3 0.9800 n
C4 O5 1.4181(19) n
C4 H4A 0.9700 n
C4 H4B 0.9700 n
O5 H5 0.798(19) n
C6 C7 1.387(2) n
C6 C11 1.3907(19) n
C7 C8 1.381(2) n
C7 H7 0.9300 n
C8 C9 1.379(2) n
C8 H8 0.9300 n
C9 C10 1.377(2) n
C9 N12 1.466(2) n
C10 C11 1.372(2) n
C10 H10 0.9300 n
C11 H11 0.9300 n
N12 O14 1.2161(17) n
N12 O13 1.2231(16) n
O1W H1W 0.895(19) n
O1W H2W 0.90(2) n
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O5 1_545 0.91(2) 2.24(2) 3.064(2) 150.0(19) y
O5 H5 O1W 2_656 0.798(19) 2.03(2) 2.8303(19) 175.0(17) y
O1W H1W N1 . 0.895(19) 1.89(2) 2.772(2) 167(2) y
O1W H2W O1W 2_746 0.90(2) 2.00(2) 2.8971(9) 172(3) y
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_publ_flag
C3 N1 C2 C4 -112.85(14) n
C2 N1 C3 C6 112.95(15) n
C4 C2 C3 N1 103.31(15) n
N1 C2 C3 C6 -108.12(15) n
C4 C2 C3 C6 -4.8(2) n
N1 C2 C4 O5 152.10(12) n
C3 C2 C4 O5 83.41(17) n
N1 C3 C6 C7 2.3(2) n
C2 C3 C6 C7 73.8(2) n
N1 C3 C6 C11 -177.77(13) n
C2 C3 C6 C11 -106.31(16) n
C11 C6 C7 C8 1.4(2) n
C3 C6 C7 C8 -178.68(14) n
C6 C7 C8 C9 -1.0(2) n
C7 C8 C9 C10 0.2(2) n
C7 C8 C9 N12 179.60(14) n
C8 C9 C10 C11 0.1(2) n
N12 C9 C10 C11 -179.30(13) n
C9 C10 C11 C6 0.4(2) n
C7 C6 C11 C10 -1.1(2) n
C3 C6 C11 C10 178.98(14) n
C10 C9 N12 O14 1.9(2) n
C8 C9 N12 O14 -177.50(14) n
C10 C9 N12 O13 -178.12(14) n
C8 C9 N12 O13 2.5(2) n
C2 C4 O5 H5 99.5(15) n
