#------------------------------------------------------------------------------
#$Date: 2020-02-14 02:29:05 +0200 (Fri, 14 Feb 2020) $
#$Revision: 248140 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/79/4037919.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_4037919
loop_
_publ_author_name
'Nikahd, Maryam'
'Mikusek, Jiri'
'Yu, Li-Juan'
'Coote, Michelle L.'
'Banwell, Martin G.'
'Ma, Chenxi'
'Gardiner, Michael G.'
_publ_section_title
;
 Exploiting Chitin as a Source of Biologically Fixed Nitrogen: Formation
 and Full Characterization of Small-Molecule Hetero- and Carbocyclic
 Pyrolysis Products.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03438
_journal_year                    2020
_chemical_formula_moiety         'C8 H9 N O2, 0.5(H8 O4)'
_chemical_formula_sum            'C8 H13 N O4'
_chemical_formula_weight         187.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-I 2y'
_space_group_name_H-M_alt        'I 1 2/m 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.661(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6345(4)
_cell_length_b                   6.4841(5)
_cell_length_c                   25.9775(17)
_cell_measurement_reflns_used    1283
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.9780
_cell_measurement_theta_min      4.7930
_cell_volume                     944.45(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω      3.00  83.00   1.00   14.73    --   15.42  57.00 120.00   80
  2  ω     -1.00  82.00   1.00   14.73    --   15.42  57.00  30.00   83
  3  ω    -10.00  19.00   1.00   14.73    --   15.42  77.00-150.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1200753000
_diffrn_orient_matrix_UB_12      -0.0019976000
_diffrn_orient_matrix_UB_13      0.0111000000
_diffrn_orient_matrix_UB_21      -0.0376446000
_diffrn_orient_matrix_UB_22      0.0285185000
_diffrn_orient_matrix_UB_23      0.0242772000
_diffrn_orient_matrix_UB_31      -0.0123839000
_diffrn_orient_matrix_UB_32      -0.1056263000
_diffrn_orient_matrix_UB_33      0.0063518000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            2008
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.857
_diffrn_reflns_theta_min         3.641
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         1159
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0394
_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)+(0.0513P)²+0.5561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1044
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1034
_reflns_number_total             1159
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03438_si_002.cif
_cod_data_source_block           mn-10p1cscaled
_cod_original_cell_volume        944.44(12)
_cod_database_code               4037919
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C8 H13 O4 N1'
_chemical_oxdiff_usercomment     'cut rods'
_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_max   0.979
_shelx_estimated_absorpt_t_min   0.974
_reflns_odcompleteness_completeness 98.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H) groups, All C(H,H) groups, All O(H,H) groups, All O(H,H,H) groups
2. Restrained distances
 O3-H3A = O3-H3B = O3-H3C
 0.85 with sigma of 0.02
 O4-H4A = O4-H4B
 0.85 with sigma of 0.02
3. Others
 Fixed Sof: H3B(0.25) H3C(0.25) H4A(0.75) H4B(0.25)
4.a Fixed occupancy and ADP/Uiso:
 H3A, H3B, H3C, H4A, H4B, H1A, H1B, H3, H5, H6, H8A, H8B
;
_ins_header
;
TITL MN-10P1Cscaled in I2/m 
REM I2/m (#12 in standard setting)
CELL 0.71073   5.634492   6.484053  25.977550  90.0000  95.6615  90.0000
ZERR    4.00   0.000386   0.000499   0.001745   0.0000   0.0067   0.0000
LATT  2
SYMM -x, y,-z 
SFAC C H N O
UNIT 32.00 52.00 4.00 16.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.166
_oxdiff_exptl_absorpt_empirical_full_min 0.857
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z+1/2'
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 0.2584(2) 0.500000 0.62989(5) 0.0256(3) Uani 1 2 d S T P . .
O2 O 0.9978(2) 0.500000 0.85963(5) 0.0266(3) Uani 1 2 d S T P . .
O3 O 1.1638(2) 0.500000 0.96435(5) 0.0278(3) Uani 1 2 d DS T P . .
H3A H 1.109(4) 0.500000 0.9328(7) 0.042 Uiso 1 2 d DS T P . .
H3B H 1.061(7) 0.500000 0.9863(16) 0.042 Uiso 0.5 2 d DS T P . .
H3C H 1.267(9) 0.591(8) 0.974(2) 0.042 Uiso 0.25 1 d D . . . .
O4 O 1.500000 0.7911(2) 1.000000 0.0416(4) Uani 1 2 d DS T P . .
H4A H 1.393(4) 0.718(4) 0.9859(10) 0.062 Uiso 0.75 1 d D . . . .
H4B H 1.500000 0.921(3) 1.000000 0.062 Uiso 0.5 2 d DS T P . .
N1 N 0.6169(2) 0.500000 0.67408(5) 0.0205(3) Uani 1 2 d S T P . .
C1 C 0.5916(4) 0.500000 0.57745(7) 0.0269(4) Uani 1 2 d S T P . .
H1A H 0.533(3) 0.620(3) 0.5580(6) 0.040 Uiso 1 1 d . . . . .
H1B H 0.766(4) 0.500000 0.5817(9) 0.040 Uiso 1 2 d S T P . .
C2 C 0.5002(3) 0.500000 0.62903(7) 0.0206(4) Uani 1 2 d S T P . .
C3 C 0.2250(3) 0.500000 0.68150(7) 0.0259(4) Uani 1 2 d S T P . .
H3 H 0.063(4) 0.500000 0.6903(9) 0.039 Uiso 1 2 d S T P . .
C4 C 0.4408(3) 0.500000 0.70881(7) 0.0208(4) Uani 1 2 d S T P . .
C5 C 0.4972(3) 0.500000 0.76446(6) 0.0207(4) Uani 1 2 d S T P . .
H5 H 0.362(4) 0.500000 0.7847(9) 0.031 Uiso 1 2 d S T P . .
C6 C 0.7203(3) 0.500000 0.78736(7) 0.0220(4) Uani 1 2 d S T P . .
H6 H 0.854(4) 0.500000 0.7668(8) 0.033 Uiso 1 2 d S T P . .
C7 C 0.7854(3) 0.500000 0.84322(6) 0.0205(4) Uani 1 2 d S T P . .
C8 C 0.5959(3) 0.500000 0.87974(7) 0.0274(4) Uani 1 2 d S T P . .
H8A H 0.661(5) 0.500000 0.9154(10) 0.041 Uiso 1 2 d S T P . .
H8B H 0.490(3) 0.615(3) 0.8742(6) 0.041 Uiso 1 1 d . . . . .
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -2 -35 0.0699
-1 2 35 0.0699
7 2 -20 0.0979
-7 -2 20 0.0979
0 -9 6 0.0802
0 9 -6 0.0802
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
C2 O1 C3 104.43(13) . . ?
C2 N1 C4 104.72(14) . . ?
O1 C2 C1 116.82(15) . . ?
N1 C2 O1 114.04(15) . . ?
N1 C2 C1 129.14(16) . . ?
C4 C3 O1 108.13(15) . . ?
N1 C4 C5 122.74(15) . . ?
C3 C4 N1 108.68(15) . . ?
C3 C4 C5 128.58(16) . . ?
C6 C5 C4 123.23(16) . . ?
C5 C6 C7 125.07(16) . . ?
O2 C7 C6 118.96(16) . . ?
O2 C7 C8 120.72(16) . . ?
C6 C7 C8 120.32(15) . . ?
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
O1 C2 1.365(2) . ?
O1 C3 1.372(2) . ?
O2 C7 1.230(2) . ?
N1 C2 1.285(2) . ?
N1 C4 1.406(2) . ?
C1 C2 1.482(2) . ?
C3 C4 1.346(2) . ?
C4 C5 1.449(2) . ?
C5 C6 1.337(2) . ?
C6 C7 1.461(2) . ?
C7 C8 1.497(2) . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 -2.0000 -34.9992 -0.2644 -0.9444 -0.0234
-1.0000 2.0000 34.9992 0.2644 0.9444 0.0234
7.0000 2.0000 -19.9988 0.6145 -0.6920 -0.4250
-7.0000 -2.0000 19.9988 -0.6145 0.6920 0.4250
0.0001 -9.0000 6.0002 0.0846 -0.1110 0.9888
-0.0001 9.0000 -6.0002 -0.0846 0.1110 -0.9888
