#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:51:08 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258141 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/00/7240050.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_7240050
loop_
_publ_author_name
'Záborský, Ondrej'
'Petrovičová, Ľudmila'
'Doháňošová, Jana'
'Moncol, Ján'
'Fischer, Róbert'
_publ_section_title
;
 Simple and efficient synthesis of bicyclic enol-carbamates: access to
 brabantamides and their analogues
;
_journal_issue                   12
_journal_name_full               'RSC Advances'
_journal_page_first              6790
_journal_page_last               6793
_journal_paper_doi               10.1039/D0RA00796J
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C9 H11 N O4'
_chemical_formula_sum            'C9 H11 N O4'
_chemical_formula_weight         197.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-17 deposited with the CCDC.	2020-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.2347(2)
_cell_length_b                   12.4282(2)
_cell_length_c                   20.6075(3)
_cell_measurement_reflns_used    132629
_cell_measurement_temperature    100
_cell_measurement_theta_max      73.86
_cell_measurement_theta_min      3.56
_cell_volume                     1852.91(7)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari with Xenocs Genix3D Cu HF'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0061
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            64018
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         73.415
_diffrn_reflns_theta_min         4.154
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.952
_exptl_absorpt_correction_T_max  0.584
_exptl_absorpt_correction_T_min  0.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       0.0024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0265
_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)+(0.0438P)²+0.3573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0718
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3674
_reflns_number_total             3678
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra00796j2.cif
_cod_data_source_block           16a
_cod_depositor_comments
'Adding full bibliography for 7240050--7240052.cif.'
_cod_database_code               7240050
_shelx_shelxl_version_number     2018/3
_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   0.825
_shelx_estimated_absorpt_t_min   0.647
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1A(H1A), C1B(H1B)
2.b Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C4B(H4BA,H4BB), C5B(H5BA,
 H5BB), C6B(H6BA,H6BB)
2.c Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C7B(H7B)
2.d Idealised Me refined as rotating group:
 C9A(H9AA,H9AB,H9AC), C9B(H9BA,H9BB,H9BC)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
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
O1A O 0.33043(17) 0.55250(9) 0.54246(5) 0.0250(3) Uani 1 1 d . . . . .
O2A O 0.39632(19) 0.66351(11) 0.45900(5) 0.0312(3) Uani 1 1 d . . . . .
O3A O 0.28281(18) 0.56286(9) 0.74776(5) 0.0262(3) Uani 1 1 d . . . . .
O4A O 0.21553(18) 0.38629(9) 0.74018(5) 0.0246(3) Uani 1 1 d . . . . .
N1A N 0.4398(2) 0.71599(11) 0.56557(6) 0.0206(3) Uani 1 1 d . . . . .
C1A C 0.3702(2) 0.67437(12) 0.62779(7) 0.0189(3) Uani 1 1 d . . . . .
H1A H 0.469090 0.674656 0.661694 0.023 Uiso 1 1 calc R . . . .
C2A C 0.3182(2) 0.56160(13) 0.60898(7) 0.0204(3) Uani 1 1 d . . . . .
C3A C 0.3918(2) 0.64981(13) 0.51638(8) 0.0227(3) Uani 1 1 d . . . . .
C4A C 0.4073(3) 0.83333(13) 0.55991(8) 0.0266(4) Uani 1 1 d . . . . .
H4AA H 0.337416 0.850463 0.519933 0.032 Uiso 1 1 calc R . . . .
H4AB H 0.525665 0.873337 0.559422 0.032 Uiso 1 1 calc R . . . .
C5A C 0.2935(3) 0.86097(12) 0.62096(8) 0.0249(3) Uani 1 1 d . . . . .
H5AA H 0.373040 0.894035 0.654592 0.030 Uiso 1 1 calc R . . . .
H5AB H 0.192435 0.911599 0.610200 0.030 Uiso 1 1 calc R . . . .
C6A C 0.2152(2) 0.75326(12) 0.64472(8) 0.0223(3) Uani 1 1 d . . . . .
H6AA H 0.191553 0.754678 0.692032 0.027 Uiso 1 1 calc R . . . .
H6AB H 0.099328 0.734763 0.621752 0.027 Uiso 1 1 calc R . . . .
C7A C 0.2680(2) 0.47672(12) 0.64430(8) 0.0219(3) Uani 1 1 d . . . . .
H7A H 0.238546 0.410967 0.623189 0.026 Uiso 1 1 calc R . . . .
C8A C 0.2575(2) 0.48318(12) 0.71524(8) 0.0207(3) Uani 1 1 d . . . . .
C9A C 0.2012(3) 0.38208(13) 0.80998(8) 0.0270(4) Uani 1 1 d . . . . .
H9AA H 0.092585 0.423048 0.824028 0.040 Uiso 1 1 calc GR . . . .
H9AB H 0.312621 0.413283 0.829389 0.040 Uiso 1 1 calc GR . . . .
H9AC H 0.188602 0.307045 0.823915 0.040 Uiso 1 1 calc GR . . . .
O1B O 0.26999(17) 0.05619(8) 0.48796(5) 0.0220(2) Uani 1 1 d . . . . .
O2B O 0.26866(18) 0.16987(10) 0.57389(5) 0.0268(3) Uani 1 1 d . . . . .
O3B O 0.2105(2) 0.06637(9) 0.28270(5) 0.0284(3) Uani 1 1 d . . . . .
O4B O 0.28473(18) -0.10954(9) 0.28656(5) 0.0248(3) Uani 1 1 d . . . . .
N1B N 0.16934(19) 0.22407(10) 0.47234(6) 0.0192(3) Uani 1 1 d . . . . .
C1B C 0.1913(2) 0.17972(12) 0.40654(7) 0.0194(3) Uani 1 1 d . . . . .
H1B H 0.071295 0.180979 0.382454 0.023 Uiso 1 1 calc R . . . .
C2B C 0.2488(2) 0.06597(12) 0.42179(7) 0.0197(3) Uani 1 1 d . . . . .
C3B C 0.2376(2) 0.15609(12) 0.51735(7) 0.0206(3) Uani 1 1 d . . . . .
C4B C 0.2177(2) 0.34002(12) 0.47454(8) 0.0226(3) Uani 1 1 d . . . . .
H4BA H 0.321429 0.353300 0.504827 0.027 Uiso 1 1 calc R . . . .
H4BB H 0.110252 0.384018 0.487995 0.027 Uiso 1 1 calc R . . . .
C5B C 0.2738(3) 0.36504(12) 0.40436(8) 0.0270(4) Uani 1 1 d . . . . .
H5BA H 0.378021 0.416645 0.403284 0.032 Uiso 1 1 calc R . . . .
H5BB H 0.168596 0.395967 0.379958 0.032 Uiso 1 1 calc R . . . .
C6B C 0.3316(3) 0.25632(12) 0.37545(8) 0.0239(3) Uani 1 1 d . . . . .
H6BA H 0.320872 0.256362 0.327555 0.029 Uiso 1 1 calc R . . . .
H6BB H 0.459788 0.237343 0.387797 0.029 Uiso 1 1 calc R . . . .
C7B C 0.2783(2) -0.01901(12) 0.38392(7) 0.0209(3) Uani 1 1 d . . . . .
H7B H 0.315918 -0.085112 0.402945 0.025 Uiso 1 1 calc R . . . .
C8B C 0.2540(2) -0.01258(12) 0.31322(7) 0.0210(3) Uani 1 1 d . . . . .
C9B C 0.2612(3) -0.11579(13) 0.21676(7) 0.0280(4) Uani 1 1 d . . . . .
H9BA H 0.349902 -0.067729 0.195523 0.042 Uiso 1 1 calc GR . . . .
H9BB H 0.135150 -0.093990 0.205310 0.042 Uiso 1 1 calc GR . . . .
H9BC H 0.282558 -0.189867 0.202299 0.042 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
C2A O1A C3A 109.40(12) . . ?
C8A O4A C9A 115.46(12) . . ?
C1A N1A C4A 111.12(12) . . ?
C3A N1A C1A 110.60(13) . . ?
C3A N1A C4A 119.97(13) . . ?
N1A C1A H1A 111.3 . . ?
N1A C1A C2A 100.88(12) . . ?
N1A C1A C6A 102.96(12) . . ?
C2A C1A H1A 111.3 . . ?
C2A C1A C6A 118.25(14) . . ?
C6A C1A H1A 111.3 . . ?
O1A C2A C1A 108.49(13) . . ?
C7A C2A O1A 119.73(14) . . ?
C7A C2A C1A 131.77(14) . . ?
O2A C3A O1A 120.87(15) . . ?
O2A C3A N1A 130.44(16) . . ?
N1A C3A O1A 108.70(13) . . ?
N1A C4A H4AA 111.0 . . ?
N1A C4A H4AB 111.0 . . ?
N1A C4A C5A 103.87(12) . . ?
H4AA C4A H4AB 109.0 . . ?
C5A C4A H4AA 111.0 . . ?
C5A C4A H4AB 111.0 . . ?
C4A C5A H5AA 110.7 . . ?
C4A C5A H5AB 110.7 . . ?
H5AA C5A H5AB 108.8 . . ?
C6A C5A C4A 105.26(12) . . ?
C6A C5A H5AA 110.7 . . ?
C6A C5A H5AB 110.7 . . ?
C1A C6A C5A 102.46(13) . . ?
C1A C6A H6AA 111.3 . . ?
C1A C6A H6AB 111.3 . . ?
C5A C6A H6AA 111.3 . . ?
C5A C6A H6AB 111.3 . . ?
H6AA C6A H6AB 109.2 . . ?
C2A C7A H7A 119.5 . . ?
C2A C7A C8A 121.04(14) . . ?
C8A C7A H7A 119.5 . . ?
O3A C8A O4A 123.76(14) . . ?
O3A C8A C7A 126.12(14) . . ?
O4A C8A C7A 110.12(13) . . ?
O4A C9A H9AA 109.5 . . ?
O4A C9A H9AB 109.5 . . ?
O4A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C2B O1B C3B 109.33(12) . . ?
C8B O4B C9B 115.74(12) . . ?
C1B N1B C4B 111.50(12) . . ?
C3B N1B C1B 111.07(12) . . ?
C3B N1B C4B 120.09(13) . . ?
N1B C1B H1B 111.0 . . ?
N1B C1B C2B 100.89(12) . . ?
N1B C1B C6B 102.94(12) . . ?
C2B C1B H1B 111.0 . . ?
C2B C1B C6B 119.15(14) . . ?
C6B C1B H1B 111.0 . . ?
O1B C2B C1B 108.66(12) . . ?
C7B C2B O1B 119.51(14) . . ?
C7B C2B C1B 131.82(14) . . ?
O2B C3B O1B 121.01(14) . . ?
O2B C3B N1B 130.38(15) . . ?
N1B C3B O1B 108.61(12) . . ?
N1B C4B H4BA 111.1 . . ?
N1B C4B H4BB 111.1 . . ?
N1B C4B C5B 103.33(12) . . ?
H4BA C4B H4BB 109.1 . . ?
C5B C4B H4BA 111.1 . . ?
C5B C4B H4BB 111.1 . . ?
C4B C5B H5BA 110.7 . . ?
C4B C5B H5BB 110.7 . . ?
C4B C5B C6B 105.05(12) . . ?
H5BA C5B H5BB 108.8 . . ?
C6B C5B H5BA 110.7 . . ?
C6B C5B H5BB 110.7 . . ?
C1B C6B C5B 101.77(13) . . ?
C1B C6B H6BA 111.4 . . ?
C1B C6B H6BB 111.4 . . ?
C5B C6B H6BA 111.4 . . ?
C5B C6B H6BB 111.4 . . ?
H6BA C6B H6BB 109.3 . . ?
C2B C7B H7B 119.4 . . ?
C2B C7B C8B 121.26(14) . . ?
C8B C7B H7B 119.4 . . ?
O3B C8B O4B 124.01(14) . . ?
O3B C8B C7B 126.30(14) . . ?
O4B C8B C7B 109.68(13) . . ?
O4B C9B H9BA 109.5 . . ?
O4B C9B H9BB 109.5 . . ?
O4B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 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
O1A C2A 1.3783(18) . ?
O1A C3A 1.396(2) . ?
O2A C3A 1.195(2) . ?
O3A C8A 1.2098(19) . ?
O4A C8A 1.3440(18) . ?
O4A C9A 1.4431(19) . ?
N1A C1A 1.4715(19) . ?
N1A C3A 1.351(2) . ?
N1A C4A 1.482(2) . ?
C1A H1A 1.0000 . ?
C1A C2A 1.502(2) . ?
C1A C6A 1.530(2) . ?
C2A C7A 1.332(2) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C5A 1.542(2) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5A C6A 1.534(2) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C7A H7A 0.9500 . ?
C7A C8A 1.466(2) . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
O1B C2B 1.3775(17) . ?
O1B C3B 1.4012(19) . ?
O2B C3B 1.1990(19) . ?
O3B C8B 1.207(2) . ?
O4B C8B 1.3430(19) . ?
O4B C9B 1.4504(18) . ?
N1B C1B 1.4722(19) . ?
N1B C3B 1.348(2) . ?
N1B C4B 1.4836(19) . ?
C1B H1B 1.0000 . ?
C1B C2B 1.507(2) . ?
C1B C6B 1.532(2) . ?
C2B C7B 1.331(2) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.534(2) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C5B C6B 1.535(2) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B H7B 0.9500 . ?
C7B C8B 1.470(2) . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?
