#------------------------------------------------------------------------------
#$Date: 2017-01-11 07:35:17 +0100 (Wed 11 de Jan de 2017) $
#$Revision: 190378 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/74/7227414.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_7227414
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         'C2 H4 N2 O3'
_chemical_formula_sum            'C2 H4 N2 O3'
_chemical_formula_weight         104.07
_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/cc1jjwc9
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-19 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.205(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.8755(14)
_cell_length_b                   5.9345(18)
_cell_length_c                   7.808(2)
_cell_measurement_reflns_used    884
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      2.64
_cell_volume                     223.00(11)
_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 1.000
_diffrn_measured_fraction_theta_max 0.953
_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  0.0248
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2534
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.153
_diffrn_reflns_theta_min         2.643
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.9856
_exptl_absorpt_correction_T_min  0.9178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             108
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     43
_refine_ls_number_reflns         569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0471
_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)+(0.0769P)²+0.0235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1301
_reflns_Friedel_coverage         0.000
_reflns_number_gt                468
_reflns_number_total             569
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ra24421a2.cif
_cod_data_source_block           1416401
_cod_original_cell_volume        223.01(11)
_cod_database_code               7227414
_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   0.918
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_file
;

    zj23mabs.res created by SHELXL-2014/7


TITL zj23mabs in P2(1)/m
CELL 0.71073   4.8755   5.9345   7.8083  90.000  99.205  90.000
ZERR    2.00   0.0014   0.0018   0.0023   0.000   0.003   0.000
LATT  1
SYMM -X, 0.5+Y, -Z
SFAC C H N O
UNIT 4 8 4 6
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
TEMP -173.000
SIZE 0.100 0.200 0.600

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

WGHT    0.076900    0.023500
FVAR       0.45954
O1    4   -0.084633    0.250000   -0.414499    10.50000    0.02979    0.04997 =
         0.02775    0.00000   -0.00478    0.00000
O2    4    0.550267    0.250000   -0.032940    10.50000    0.01335    0.02797 =
         0.03598    0.00000    0.00646    0.00000
O3    4    0.218380    0.250000    0.138879    10.50000    0.01759    0.02845 =
         0.02529    0.00000    0.00559    0.00000
N1    3    0.083803    0.250000   -0.143721    10.50000    0.01201    0.02749 =
         0.02641    0.00000    0.00551    0.00000
AFIX  43
H1A   2   -0.086520    0.250000   -0.119739    10.50000   -1.20000
AFIX   0
N2    3    0.129513    0.250000   -0.310267    10.50000    0.02499    0.03160 =
         0.02678    0.00000    0.00479    0.00000
C1    1    0.310641    0.250000   -0.011876    10.50000    0.01582    0.01613 =
         0.02879    0.00000    0.00670    0.00000
C2    1    0.429422    0.250000    0.292857    10.50000    0.02663    0.03384 =
         0.02624    0.00000    0.00081    0.00000
AFIX  33
H2A   2    0.339700    0.250000    0.396562    10.50000   -1.50000
H2B   2    0.545500    0.115167    0.292965    10.50000   -1.50000
H2C   2    0.545500    0.384833    0.292965    10.50000   -1.50000

REM #####
AFIX   0
HKLF 4

REM  zj23mabs in P2(1)/m
REM R1 =  0.0471 for     468 Fo > 4sig(Fo)  and  0.0589 for all     569 data
REM     43 parameters refined using      0 restraints

END

WGHT      0.0769      0.0235

REM Highest difference peak  0.417,  deepest hole -0.286,  1-sigma level  0.072
Q1    1   0.3016  0.2500 -0.3497  10.50000  0.05    0.42
Q2    1  -0.2298  0.2500 -0.3415  10.50000  0.05    0.26
Q3    1   0.2936  0.1838  0.0808  11.00000  0.05    0.25
Q4    1   0.6122  0.2500  0.2512  10.50000  0.05    0.24
Q5    1   0.1329  0.1472  0.1574  11.00000  0.05    0.24
;
_shelx_res_checksum              62742
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
O1 O -0.0846(4) 0.2500 -0.4145(2) 0.0369(5) Uani 1 2 d S T P
O2 O 0.5503(3) 0.2500 -0.0329(2) 0.0255(5) Uani 1 2 d S T P
O3 O 0.2184(3) 0.2500 0.1389(2) 0.0235(4) Uani 1 2 d S T P
N1 N 0.0838(3) 0.2500 -0.1437(2) 0.0217(5) Uani 1 2 d S T P
H1A H -0.0865 0.2500 -0.1197 0.026 Uiso 1 2 calc R U P
N2 N 0.1295(4) 0.2500 -0.3103(3) 0.0277(5) Uani 1 2 d S T P
C1 C 0.3106(4) 0.2500 -0.0119(3) 0.0199(5) Uani 1 2 d S T P
C2 C 0.4294(5) 0.2500 0.2929(3) 0.0293(6) Uani 1 2 d S T P
H2A H 0.3397 0.2500 0.3966 0.044 Uiso 1 2 calc R U P
H2B H 0.5455 0.1152 0.2930 0.044 Uiso 0.5 1 calc R U P
H2C H 0.5455 0.3848 0.2930 0.044 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 0.0298(9) 0.0500(12) 0.0277(9) 0.000 -0.0048(7) 0.000
O2 0.0134(7) 0.0280(8) 0.0360(10) 0.000 0.0065(6) 0.000
O3 0.0176(7) 0.0284(8) 0.0253(9) 0.000 0.0056(6) 0.000
N1 0.0120(8) 0.0275(10) 0.0264(10) 0.000 0.0055(7) 0.000
N2 0.0250(10) 0.0316(11) 0.0268(11) 0.000 0.0048(8) 0.000
C1 0.0158(9) 0.0161(10) 0.0288(12) 0.000 0.0067(8) 0.000
C2 0.0266(11) 0.0338(12) 0.0262(13) 0.000 0.0008(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 116.05(18)
N2 N1 C1 118.64(17)
N2 N1 H1A 120.7
C1 N1 H1A 120.7
O1 N2 N1 112.76(19)
O2 C1 O3 126.5(2)
O2 C1 N1 125.1(2)
O3 C1 N1 108.42(17)
O3 C2 H2A 109.5
O3 C2 H2B 109.5
H2A C2 H2B 109.5
O3 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N2 1.217(3)
O2 C1 1.206(2)
O3 C1 1.326(3)
O3 C2 1.452(3)
N1 N2 1.354(3)
N1 C1 1.385(3)
N1 H1A 0.8800
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 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 O1 180.000(0)
C2 O3 C1 O2 0.000(0)
C2 O3 C1 N1 180.000(0)
N2 N1 C1 O2 0.000(0)
N2 N1 C1 O3 180.000(0)
