#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/13/4021367.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_4021367
loop_
_publ_author_name
'Arnaud Salaün'
'Annaïck Favre'
'Barbara Le Grel'
'Michel Potel'
'Philippe Le Grel'
_publ_section_title
;
 Conformation of N^α^-Substituted Hydrazino Acetamides in CDCl₃,
 he Precious Help of the Analysis of Δδ between Amidic Hydrogens,
 and Correlation to the Conformation of Aza-β³-peptides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              150
_journal_page_last               158
_journal_paper_doi               10.1021/jo051887q
_journal_volume                  71
_journal_year                    2006
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C9 H12 N2 O1'
_chemical_formula_sum            'C9 H12 N2 O'
_chemical_formula_weight         164.21
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2005-03-22T16:02:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 99.626(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0907(2)
_cell_length_b                   5.1112(2)
_cell_length_c                   17.8226(8)
_cell_measurement_reflns_used    2199
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.546
_cell_measurement_wavelength     0.71073
_cell_volume                     906.27(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.762653E-1
_diffrn_orient_matrix_UB_12      0.35417E-1
_diffrn_orient_matrix_UB_13      0.04233
_diffrn_orient_matrix_UB_21      -0.654047E-1
_diffrn_orient_matrix_UB_22      0.324089E-1
_diffrn_orient_matrix_UB_23      0.353874E-1
_diffrn_orient_matrix_UB_31      0.30653E-2
_diffrn_orient_matrix_UB_32      -0.189667
_diffrn_orient_matrix_UB_33      0.139511E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3693
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.07(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2070
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0899P)²+0.1025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1692
_reflns_number_gt                1419
_reflns_number_total             2070
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo051887qsi20050908_052214.cif
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               4021367
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.15753(11) 0.87142(19) 0.05171(7) 0.0612(4) Uani 1 1 d .
N2 N 0.16078(13) 0.4333(3) 0.05741(8) 0.0509(4) Uani 1 1 d .
N3 N -0.03414(15) 0.4152(3) 0.14518(8) 0.0599(4) Uani 1 1 d .
C4 C 0.11795(13) 0.6637(3) 0.07598(8) 0.0435(4) Uani 1 1 d .
C5 C 0.01726(16) 0.6708(3) 0.12974(9) 0.0539(4) Uani 1 1 d .
H5A H 0.0593 0.749 0.1774 0.065 Uiso 1 1 calc R
H5B H -0.0575 0.7817 0.1081 0.065 Uiso 1 1 calc R
C6 C -0.02004(18) 0.4618(4) 0.28399(9) 0.0636(5) Uani 1 1 d .
C7 C -0.10985(18) 0.4179(4) 0.20847(10) 0.0744(6) Uani 1 1 d .
H7A H -0.1565 0.2524 0.2098 0.089 Uiso 1 1 calc R
H7B H -0.1769 0.5555 0.2001 0.089 Uiso 1 1 calc R
C8 C 0.0953(2) 0.3171(4) 0.30485(12) 0.0823(6) Uani 1 1 d .
H8 H 0.1188 0.1933 0.2712 0.099 Uiso 1 1 calc R
C9 C -0.0513(3) 0.6432(4) 0.33448(14) 0.0958(7) Uani 1 1 d .
H9 H -0.1279 0.7457 0.3217 0.115 Uiso 1 1 calc R
C10 C 0.1766(3) 0.3506(5) 0.37409(14) 0.1017(8) Uani 1 1 d .
H10 H 0.2545 0.2516 0.3867 0.122 Uiso 1 1 calc R
C11 C 0.1428(4) 0.5274(6) 0.42349(14) 0.1147(10) Uani 1 1 d .
H11 H 0.1968 0.548 0.4708 0.138 Uiso 1 1 calc R
C12 C 0.0306(4) 0.6761(6) 0.40504(16) 0.1245(11) Uani 1 1 d .
H12 H 0.0085 0.7993 0.4393 0.149 Uiso 1 1 calc R
H3 H -0.086(2) 0.363(4) 0.1035(12) 0.077(6) Uiso 1 1 d .
H2A H 0.1288(17) 0.294(4) 0.0744(9) 0.059(5) Uiso 1 1 d .
H2B H 0.2209(18) 0.418(3) 0.0219(10) 0.060(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
O1 0.0732(8) 0.0358(6) 0.0823(8) 0.0036(5) 0.0358(6) -0.0015(5)
N2 0.0596(8) 0.0344(7) 0.0622(8) 0.0041(6) 0.0205(6) 0.0004(5)
N3 0.0648(8) 0.0647(9) 0.0523(8) -0.0018(7) 0.0158(6) -0.0201(7)
C4 0.0464(7) 0.0360(7) 0.0483(8) 0.0009(6) 0.0084(6) -0.0017(5)
C5 0.0580(9) 0.0491(9) 0.0579(9) -0.0026(7) 0.0194(7) -0.0037(7)
C6 0.0731(11) 0.0665(11) 0.0574(9) 0.0044(8) 0.0287(8) -0.0082(9)
C7 0.0624(10) 0.0991(14) 0.0660(11) 0.0080(10) 0.0237(8) -0.0162(10)
C8 0.0919(14) 0.0880(14) 0.0692(12) -0.0046(10) 0.0198(10) 0.0054(11)
C9 0.1206(19) 0.0886(16) 0.0857(15) -0.0057(12) 0.0388(13) 0.0136(13)
C10 0.1080(18) 0.120(2) 0.0738(14) 0.0074(13) 0.0047(12) 0.0032(15)
C11 0.151(3) 0.125(2) 0.0644(14) -0.0062(14) 0.0088(16) -0.016(2)
C12 0.192(3) 0.104(2) 0.0848(17) -0.0303(15) 0.047(2) -0.003(2)
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.12
-1 0 0 0.14
0 1 0 0.4
0 -1 0 0.35
0 0 1 0.2
0 0 -1 0.2
1 0 1 0.15
-1 0 -1 0.15
-1 0 1 0.22
1 0 -1 0.22
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 N2 H2A 119.8(12)
C4 N2 H2B 121.0(11)
H2A N2 H2B 118.9(15)
C5 N3 C7 112.78(14)
C5 N3 H3 107.3(13)
C7 N3 H3 109.8(14)
O1 C4 N2 122.76(13)
O1 C4 C5 119.50(12)
N2 C4 C5 117.74(12)
N3 C5 C4 113.54(12)
N3 C5 H5A 108.9
C4 C5 H5A 108.9
N3 C5 H5B 108.9
C4 C5 H5B 108.9
H5A C5 H5B 107.7
C9 C6 C8 117.7(2)
C9 C6 C7 121.3(2)
C8 C6 C7 121.04(17)
N3 C7 C6 112.07(14)
N3 C7 H7A 109.2
C6 C7 H7A 109.2
N3 C7 H7B 109.2
C6 C7 H7B 109.2
H7A C7 H7B 107.9
C10 C8 C6 121.8(2)
C10 C8 H8 119.1
C6 C8 H8 119.1
C6 C9 C12 120.6(2)
C6 C9 H9 119.7
C12 C9 H9 119.7
C11 C10 C8 119.6(3)
C11 C10 H10 120.2
C8 C10 H10 120.2
C10 C11 C12 120.7(2)
C10 C11 H11 119.7
C12 C11 H11 119.7
C11 C12 C9 119.7(2)
C11 C12 H12 120.2
C9 C12 H12 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.2374(16)
N2 C4 1.3157(18)
N2 H2A 0.859(19)
N2 H2B 0.95(2)
N3 C5 1.449(2)
N3 C7 1.464(2)
N3 H3 0.88(2)
C4 C5 1.509(2)
C5 H5A 0.97
C5 H5B 0.97
C6 C9 1.365(3)
C6 C8 1.377(3)
C6 C7 1.508(3)
C7 H7A 0.97
C7 H7B 0.97
C8 C10 1.373(3)
C8 H8 0.93
C9 C12 1.395(4)
C9 H9 0.93
C10 C11 1.345(4)
C10 H10 0.93
C11 C12 1.358(4)
C11 H11 0.93
C12 H12 0.93
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 383787
