#------------------------------------------------------------------------------
#$Date: 2017-01-11 07:35:17 +0100 (Wed 11 de Jan de 2017) $
#$Revision: 190378 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/74/7227415.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_7227415
loop_
_publ_author_name
'Chua, Zhijie'
'Rosadiuk, Kris'
'Perepichka, Inna'
'Bohle, Scott'
_publ_section_title
;
 Lewis Acid stabilization and Activation of Primary N-Nitrosamides
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA24421A
_journal_year                    2017
_chemical_formula_moiety         'C3 H6 N2 O3'
_chemical_formula_sum            'C3 H6 N2 O3'
_chemical_formula_weight         118.10
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/cc1jjwdb
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-01-05 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.945(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.7863(15)
_cell_length_b                   6.0338(19)
_cell_length_c                   9.375(3)
_cell_measurement_reflns_used    2603
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.21
_cell_volume                     266.68(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2603
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.206
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             124
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     55
_refine_ls_number_reflns         571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0364
_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)+(0.0393P)²+0.0825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                450
_reflns_number_total             571
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ra24421a2.cif
_cod_data_source_block           1416402
_cod_original_cell_volume        266.67(15)
_cod_database_code               7227415
_shelx_shelxl_version_number     2014/7
_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   0.949
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_file
;

    zj30mabs.res created by SHELXL-2014/7


TITL zj30mabs in P2(1)/m
CELL 0.71073   4.7863   6.0338   9.3747  90.000  99.945  90.000
ZERR    2.00   0.0015   0.0019   0.0030   0.000   0.003   0.000
LATT  1
SYMM -X, 0.5+Y, -Z
SFAC C H N O
UNIT 6 12 4 6
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
TEMP -173.000
SIZE 0.100 0.400 0.400
EADP O1 O1A
EADP O1A O4

L.S. 10
FMAP 2
BOND $H
CONF
ACTA 50
PLAN 5

WGHT    0.039300    0.082500
FVAR       1.24020
PART 1
O1    4   -0.052109    0.250000    0.211549    10.44000    0.02688    0.02630 =
         0.02183    0.00000    0.00148    0.00000
PART -3
O1A   4   -0.093155    0.267876    0.230478    10.03000    0.02688    0.02630 =
         0.02183    0.00000    0.00148    0.00000
O4    4    0.365839    0.274867    0.277568    10.03000    0.02688    0.02630 =
         0.02183    0.00000    0.00148    0.00000
PART 0
O2    4    0.587269    0.250000    0.537864    10.50000    0.01561    0.02857 =
         0.04142    0.00000    0.01029    0.00000
O3    4    0.245638    0.250000    0.675177    10.50000    0.01594    0.02871 =
         0.02349    0.00000    0.00277    0.00000
N1    3    0.114396    0.250000    0.438950    10.50000    0.01707    0.02101 =
         0.02403    0.00000    0.00733    0.00000
AFIX  43
H1A   2   -0.060209    0.250000    0.456745    10.50000   -1.20000
AFIX   0
N2    3    0.162990    0.250000    0.301319    10.50000    0.03000    0.02151 =
         0.02857    0.00000    0.00896    0.00000
C1    1    0.342929    0.250000    0.551561    10.50000    0.01900    0.01335 =
         0.02812    0.00000    0.00569    0.00000
C2    1    0.460411    0.250000    0.806076    10.50000    0.01777    0.02954 =
         0.02963    0.00000   -0.00309    0.00000
AFIX  23
H2A   2    0.581967    0.383211    0.808773    10.50000   -1.20000
H2B   2    0.581967    0.116789    0.808773    10.50000   -1.20000
AFIX   0
C3    1    0.305997    0.250000    0.932440    10.50000    0.02935    0.02549 =
         0.02484    0.00000   -0.00103    0.00000
AFIX  33
H3A   2    0.443765    0.250000    1.022869    10.50000   -1.50000
H3B   2    0.186693    0.382614    0.928486    10.50000   -1.50000
H3C   2    0.186692    0.117386    0.928486    10.50000   -1.50000

REM #####
AFIX   0
HKLF 4

REM  zj30mabs in P2(1)/m
REM R1 =  0.0364 for     450 Fo > 4sig(Fo)  and  0.0526 for all     571 data
REM     55 parameters refined using      0 restraints

END

WGHT      0.0393      0.0825

REM Highest difference peak  0.179,  deepest hole -0.207,  1-sigma level  0.043
Q1    1   0.4565  0.2500  0.3350  10.50000  0.05    0.18
Q2    1  -0.1619  0.3219  0.2070  11.00000  0.05    0.14
Q3    1   0.0331  0.2500  0.7055  10.50000  0.05    0.14
Q4    1  -0.0078  0.3261  0.2385  11.00000  0.05    0.14
Q5    1  -0.0992  0.2500  0.1503  10.50000  0.05    0.13
;
_shelx_res_checksum              52258
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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
O1 O -0.0521(12) 0.2500 0.2115(6) 0.0253(10) Uani 0.88 2 d S T P A 1
O1A O -0.09(2) 0.27(2) 0.230(11) 0.0253(10) Uani 0.03 1 d . . P A -3
O4 O 0.366(6) 0.275(9) 0.278(3) 0.0253(10) Uani 0.03 1 d . . P A -3
O2 O 0.5873(3) 0.2500 0.53786(19) 0.0279(5) Uani 1 2 d S T P A .
O3 O 0.2456(3) 0.2500 0.67518(17) 0.0228(4) Uani 1 2 d S T P A .
N1 N 0.1144(4) 0.2500 0.43895(19) 0.0203(5) Uani 1 2 d S T P A .
H1A H -0.0602 0.2500 0.4567 0.024 Uiso 1 2 calc R U P . .
N2 N 0.1630(4) 0.2500 0.3013(2) 0.0262(5) Uani 1 2 d S T P . .
C1 C 0.3429(4) 0.2500 0.5516(2) 0.0200(5) Uani 1 2 d S T P . .
C2 C 0.4604(5) 0.2500 0.8061(3) 0.0265(6) Uani 1 2 d S T P . .
H2A H 0.5820 0.3832 0.8088 0.032 Uiso 0.5 1 calc R U P A .
H2B H 0.5820 0.1168 0.8088 0.032 Uiso 0.5 1 calc R U P . .
C3 C 0.3060(5) 0.2500 0.9324(3) 0.0272(6) Uani 1 2 d S T P A .
H3A H 0.4438 0.2500 1.0229 0.041 Uiso 1 2 calc R U P . .
H3B H 0.1867 0.3826 0.9285 0.041 Uiso 0.5 1 calc R U P . .
H3C H 0.1867 0.1174 0.9285 0.041 Uiso 0.5 1 calc R U P . .
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 0.027(2) 0.026(2) 0.022(2) 0.000 0.0015(11) 0.000
O1A 0.027(2) 0.026(2) 0.022(2) 0.000 0.0015(11) 0.000
O4 0.027(2) 0.026(2) 0.022(2) 0.000 0.0015(11) 0.000
O2 0.0156(9) 0.0286(10) 0.0414(11) 0.000 0.0103(7) 0.000
O3 0.0159(8) 0.0287(9) 0.0235(9) 0.000 0.0028(6) 0.000
N1 0.0171(9) 0.0210(10) 0.0240(11) 0.000 0.0073(8) 0.000
N2 0.0300(12) 0.0215(11) 0.0286(12) 0.000 0.0090(10) 0.000
C1 0.0190(12) 0.0133(11) 0.0281(14) 0.000 0.0057(10) 0.000
C2 0.0178(12) 0.0295(15) 0.0296(14) 0.000 -0.0031(10) 0.000
C3 0.0293(13) 0.0255(14) 0.0248(14) 0.000 -0.0010(10) 0.000
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
C1 O3 C2 115.72(17)
N2 N1 C1 119.05(18)
N2 N1 H1A 120.5
C1 N1 H1A 120.5
O4 N2 O1A 135(4)
O4 N2 N1 121.6(16)
O1 N2 N1 113.4(2)
O1A N2 N1 101(4)
O2 C1 O3 126.3(2)
O2 C1 N1 125.2(2)
O3 C1 N1 108.51(17)
O3 C2 C3 107.01(18)
O3 C2 H2A 110.3
C3 C2 H2A 110.3
O3 C2 H2B 110.3
C3 C2 H2B 110.3
H2A C2 H2B 108.6
C2 C3 H3A 109.5
C2 C3 H3B 109.5
H3A C3 H3B 109.5
C2 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N2 1.212(7)
O1A N2 1.29(11)
O4 N2 1.04(3)
O2 C1 1.198(3)
O3 C1 1.321(3)
O3 C2 1.458(3)
N1 N2 1.350(3)
N1 C1 1.383(3)
N1 H1A 0.8800
C2 C3 1.501(3)
C2 H2A 0.9900
C2 H2B 0.9900
C3 H3A 0.9800
C3 H3B 0.9800
C3 H3C 0.9800
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
C1 N1 N2 O4 -10(3)
C1 N1 N2 O1 180.000(1)
C1 N1 N2 O1A -175(7)
C2 O3 C1 O2 0.000(1)
C2 O3 C1 N1 180.000(1)
N2 N1 C1 O2 0.000(1)
N2 N1 C1 O3 180.000(1)
C1 O3 C2 C3 180.000(1)
