#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:18:41 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257596 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/99/7239983.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_7239983
loop_
_publ_author_name
'Pham, Thuy Trang'
'Chen, Xi'
'Söhnel, Tilo'
'Yan, Ning'
'Sperry, Jonathan'
_publ_section_title
;
 Haber-independent, diversity-oriented synthesis of nitrogen compounds
 from biorenewable chitin
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              1978
_journal_page_last               1984
_journal_paper_doi               10.1039/D0GC00208A
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C8 H11 N O3'
_chemical_formula_sum            'C8 H11 N O3'
_chemical_formula_weight         169.18
_chemical_melting_point          137.5(6)
_chemical_name_systematic        TR67.0U
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-11-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-06 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.7246(3)
_cell_length_b                   8.3285(2)
_cell_length_c                   16.9656(5)
_cell_measurement_reflns_used    4055
_cell_measurement_temperature    106(7)
_cell_measurement_theta_max      74.6000
_cell_measurement_theta_min      5.1960
_cell_volume                     1656.66(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      106(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00 -18.00   0.50    0.10    --  -47.48 -82.00 -80.00   50
  2  ω   -118.00 -70.00   0.50    0.10    --  -47.48 -82.00 -80.00   96
  3  ω    -66.00  27.00   0.50    0.10    --  -47.48  57.00  30.00  186
  4  ω    -59.00 -14.00   0.50    0.41    --  -90.25 111.00 -60.00   90
  5  ω   -121.00 -91.00   0.50    0.41    --  -90.25  93.00 -67.00   60
  6  ω   -118.00 -77.00   0.50    0.10    --  -47.48-125.00 -30.00   82
  7  ω     28.00  73.00   0.50    0.41    --  102.39 -82.00 -80.00   90
  8  ω     70.00  96.00   0.50    0.41    --  102.39-111.00 -90.00   52
  9  ω    132.00 177.00   0.50    0.41    --  102.39  30.00 -90.00   90
 10  ω    116.00 156.00   0.50    0.41    --  102.39  93.00 -67.00   80
 11  ω    139.00 176.00   0.50    0.41    --  102.39 111.00-180.00   74
 12  ω     99.00 171.00   0.50    0.41    --  102.39  51.00-171.00  144
 13  ω     85.00 126.00   0.50    0.41    --  102.39  30.00 -90.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0350493000
_diffrn_orient_matrix_UB_12      0.0948774000
_diffrn_orient_matrix_UB_13      0.0741419000
_diffrn_orient_matrix_UB_21      0.0738309000
_diffrn_orient_matrix_UB_22      0.1425360000
_diffrn_orient_matrix_UB_23      -0.0272177000
_diffrn_orient_matrix_UB_31      -0.1028438000
_diffrn_orient_matrix_UB_32      0.0700644000
_diffrn_orient_matrix_UB_33      -0.0448231000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5662
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.695
_diffrn_reflns_theta_min         6.441
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.875
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethylacetate + light petroleum'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0375
_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)+(0.0479P)²+0.5427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0977
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1325
_reflns_number_total             1491
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0gc00208a2.cif
_cod_data_source_block           tr67_ou
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '136.9-138.1' was changed
to '137.5(6)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7239983--7239986.cif.

 Adding full bibliography for 7239983--7239986.cif.
;
_cod_database_code               7239983
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C8H11NO3
_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   0.958
_shelx_estimated_absorpt_t_min   0.887
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.62
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C8(H8A,H8B,H8C)
;
_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 1.124
_oxdiff_exptl_absorpt_empirical_full_min 0.891
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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_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 0.18163(8) 0.13614(12) 0.68774(6) 0.0263(3) Uani 1 1 d . . . . .
O2 O 0.47686(8) 0.47485(12) 0.59671(6) 0.0233(3) Uani 1 1 d . . . . .
H2 H 0.4385(18) 0.538(2) 0.6286(12) 0.044(5) Uiso 1 1 d . . . . .
O3 O 0.11837(8) 0.50877(15) 0.45549(6) 0.0355(3) Uani 1 1 d . . . . .
N1 N 0.30777(10) 0.46093(15) 0.47313(7) 0.0219(3) Uani 1 1 d . . . . .
H1 H 0.3743(16) 0.482(2) 0.4561(10) 0.029(4) Uiso 1 1 d . . . . .
C1 C 0.24239(11) 0.22159(16) 0.64556(8) 0.0226(3) Uani 1 1 d . . . . .
C2 C 0.36760(11) 0.25593(17) 0.66198(8) 0.0239(3) Uani 1 1 d . . . . .
H2A H 0.370486 0.338281 0.703197 0.029 Uiso 1 1 calc R . . . .
C3 C 0.43648(12) 0.11349(19) 0.69120(9) 0.0311(4) Uani 1 1 d . . . . .
H3A H 0.399174 0.066719 0.736031 0.047 Uiso 1 1 calc GR . . . .
H3B H 0.511416 0.148759 0.706039 0.047 Uiso 1 1 calc GR . . . .
H3C H 0.442402 0.034928 0.649994 0.047 Uiso 1 1 calc GR . . . .
C4 C 0.40917(11) 0.33459(16) 0.58517(8) 0.0214(3) Uani 1 1 d . . . . .
H4 H 0.453745 0.255842 0.555279 0.026 Uiso 1 1 calc R . . . .
C5 C 0.29992(11) 0.37055(16) 0.54032(8) 0.0210(3) Uani 1 1 d . . . . .
C6 C 0.20762(11) 0.30434(17) 0.57503(8) 0.0232(3) Uani 1 1 d . . . . .
H6 H 0.133225 0.311107 0.556316 0.028 Uiso 1 1 calc R . . . .
C7 C 0.21601(12) 0.52638(18) 0.43307(8) 0.0247(3) Uani 1 1 d . . . . .
C8 C 0.24632(13) 0.61787(19) 0.35999(8) 0.0284(4) Uani 1 1 d . . . . .
H8A H 0.246379 0.546321 0.315628 0.043 Uiso 1 1 calc GR . . . .
H8B H 0.320708 0.664453 0.365994 0.043 Uiso 1 1 calc GR . . . .
H8C H 0.191294 0.701466 0.351525 0.043 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O2 H2 106.7(13) . . ?
C5 N1 H1 117.2(12) . . ?
C5 N1 C7 124.95(12) . . ?
C7 N1 H1 117.8(12) . . ?
O1 C1 C2 123.96(12) . . ?
O1 C1 C6 126.43(12) . . ?
C6 C1 C2 109.60(11) . . ?
C1 C2 H2A 107.2 . . ?
C1 C2 C4 103.33(10) . . ?
C3 C2 C1 115.22(12) . . ?
C3 C2 H2A 107.2 . . ?
C3 C2 C4 116.16(11) . . ?
C4 C2 H2A 107.2 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 C2 114.14(11) . . ?
O2 C4 H4 108.8 . . ?
O2 C4 C5 112.11(11) . . ?
C2 C4 H4 108.8 . . ?
C5 C4 C2 103.95(10) . . ?
C5 C4 H4 108.8 . . ?
N1 C5 C4 117.94(11) . . ?
C6 C5 N1 129.92(12) . . ?
C6 C5 C4 112.14(12) . . ?
C1 C6 H6 125.3 . . ?
C5 C6 C1 109.34(12) . . ?
C5 C6 H6 125.3 . . ?
O3 C7 N1 122.07(14) . . ?
O3 C7 C8 122.95(13) . . ?
N1 C7 C8 114.97(12) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
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 C1 1.2354(17) . ?
O2 H2 0.88(2) . ?
O2 C4 1.4258(16) . ?
O3 C7 1.2152(17) . ?
N1 H1 0.850(19) . ?
N1 C5 1.3692(18) . ?
N1 C7 1.3844(19) . ?
C1 C2 1.5214(19) . ?
C1 C6 1.440(2) . ?
C2 H2A 0.9800 . ?
C2 C3 1.518(2) . ?
C2 C4 1.5379(18) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4 0.9800 . ?
C4 C5 1.5196(18) . ?
C5 C6 1.3497(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.498(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 40.50(19) . . . . ?
O1 C1 C2 C4 168.27(13) . . . . ?
O1 C1 C6 C5 -173.17(13) . . . . ?
O2 C4 C5 N1 47.79(16) . . . . ?
O2 C4 C5 C6 -132.46(12) . . . . ?
N1 C5 C6 C1 -179.25(13) . . . . ?
C1 C2 C4 O2 134.47(11) . . . . ?
C1 C2 C4 C5 12.03(14) . . . . ?
C2 C1 C6 C5 7.36(16) . . . . ?
C2 C4 C5 N1 171.56(11) . . . . ?
C2 C4 C5 C6 -8.69(15) . . . . ?
C3 C2 C4 O2 -98.35(14) . . . . ?
C3 C2 C4 C5 139.21(12) . . . . ?
C4 C5 C6 C1 1.04(16) . . . . ?
C5 N1 C7 O3 0.4(2) . . . . ?
C5 N1 C7 C8 -178.78(12) . . . . ?
C6 C1 C2 C3 -140.01(12) . . . . ?
C6 C1 C2 C4 -12.24(14) . . . . ?
C7 N1 C5 C4 -168.69(12) . . . . ?
C7 N1 C5 C6 11.6(2) . . . . ?
