#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:51:08 +0300 (Tue, 06 Oct 2020) $
#$Revision: 258141 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/00/7240051.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_7240051
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         'C8 H9 N O4'
_chemical_formula_sum            'C8 H9 N O4'
_chemical_formula_weight         183.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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                 90.4200(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.57010(10)
_cell_length_b                   7.7138(2)
_cell_length_c                   11.0161(2)
_cell_measurement_reflns_used    61898
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.08
_cell_measurement_theta_min      4.01
_cell_volume                     813.21(3)
_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 0.997
_diffrn_measured_fraction_theta_max 0.988
_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  0.0168
_diffrn_reflns_av_unetI/netI     0.0071
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            38003
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.502
_diffrn_reflns_theta_min         4.013
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.040
_exptl_absorpt_correction_T_max  0.796
_exptl_absorpt_correction_T_min  0.353
_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    1.496
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1383 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_coef       0.0064(6)
_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   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3103
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0223
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0323P)²+0.1775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0577
_refine_ls_wR_factor_ref         0.0579
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                3074
_reflns_number_total             3103
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra00796j2.cif
_cod_data_source_block           20
_cod_depositor_comments
'Adding full bibliography for 7240050--7240052.cif.'
_cod_database_code               7240051
_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   0.894
_shelx_estimated_absorpt_t_min   0.774
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C15(H15)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'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 0.18999(15) -0.15463(19) 0.55905(13) 0.0297(3) Uani 1 1 d . . . . .
O2 O 0.39372(13) -0.05126(16) 0.63646(12) 0.0219(3) Uani 1 1 d . . . . .
O3 O 0.59425(13) 0.42797(16) 0.71219(12) 0.0200(3) Uani 1 1 d . . . . .
O4 O 0.78247(12) 0.26576(17) 0.75594(11) 0.0196(3) Uani 1 1 d . . . . .
H4 H 0.815420 0.362373 0.776610 0.029 Uiso 1 1 calc GR . . . .
N1 N 0.21308(14) 0.1287(2) 0.62511(13) 0.0191(3) Uani 1 1 d . . . . .
C1 C 0.25331(19) -0.0338(3) 0.60101(16) 0.0211(4) Uani 1 1 d . . . . .
C2 C 0.10584(18) 0.2194(3) 0.55186(17) 0.0243(4) Uani 1 1 d . . . . .
H2A H 0.017250 0.230485 0.597041 0.029 Uiso 1 1 calc R . . . .
H2B H 0.087502 0.157692 0.474567 0.029 Uiso 1 1 calc R . . . .
C3 C 0.17201(19) 0.3977(3) 0.52903(17) 0.0226(4) Uani 1 1 d . . . . .
H3A H 0.135596 0.484609 0.586901 0.027 Uiso 1 1 calc R . . . .
H3B H 0.151834 0.437665 0.445308 0.027 Uiso 1 1 calc R . . . .
C4 C 0.33012(18) 0.3709(2) 0.54807(15) 0.0199(4) Uani 1 1 d . . . . .
H4A H 0.374416 0.322607 0.474514 0.024 Uiso 1 1 calc R . . . .
H4B H 0.377310 0.480600 0.570653 0.024 Uiso 1 1 calc R . . . .
C5 C 0.33303(16) 0.2409(2) 0.65276(15) 0.0168(3) Uani 1 1 d . . . . .
H5 H 0.319699 0.301444 0.732124 0.020 Uiso 1 1 calc R . . . .
C6 C 0.44831(18) 0.1093(2) 0.66240(15) 0.0168(3) Uani 1 1 d . . . . .
C7 C 0.58298(19) 0.1213(2) 0.69256(16) 0.0187(4) Uani 1 1 d . . . . .
H7 H 0.636941 0.018046 0.696506 0.022 Uiso 1 1 calc R . . . .
C8 C 0.65107(17) 0.2855(2) 0.71974(15) 0.0168(3) Uani 1 1 d . . . . .
O5 O 1.31063(13) 1.15226(17) 0.94351(12) 0.0221(3) Uani 1 1 d . . . . .
O6 O 1.09981(12) 1.04406(15) 0.88781(11) 0.0168(3) Uani 1 1 d . . . . .
O7 O 0.89842(13) 0.56237(16) 0.82226(11) 0.0190(3) Uani 1 1 d . . . . .
O8 O 0.72065(12) 0.72411(17) 0.75139(11) 0.0216(3) Uani 1 1 d . . . . .
H8 H 0.683383 0.626350 0.742174 0.032 Uiso 1 1 calc GR . . . .
N2 N 1.25551(14) 0.8622(2) 0.96791(12) 0.0163(3) Uani 1 1 d . . . . .
C9 C 1.23502(18) 1.0282(2) 0.93614(15) 0.0170(4) Uani 1 1 d . . . . .
C10 C 1.39275(16) 0.7751(3) 0.96023(16) 0.0203(4) Uani 1 1 d . . . . .
H10A H 1.440099 0.771630 1.040395 0.024 Uiso 1 1 calc R . . . .
H10B H 1.454232 0.833825 0.901189 0.024 Uiso 1 1 calc R . . . .
C11 C 1.35354(18) 0.5929(3) 0.91709(17) 0.0224(4) Uani 1 1 d . . . . .
H11A H 1.341011 0.513855 0.986973 0.027 Uiso 1 1 calc R . . . .
H11B H 1.426677 0.544981 0.863575 0.027 Uiso 1 1 calc R . . . .
C12 C 1.21560(17) 0.6166(2) 0.84718(16) 0.0201(4) Uani 1 1 d . . . . .
H12A H 1.231616 0.661495 0.764253 0.024 Uiso 1 1 calc R . . . .
H12B H 1.162387 0.506735 0.842153 0.024 Uiso 1 1 calc R . . . .
C13 C 1.14087(16) 0.7505(2) 0.92653(14) 0.0156(3) Uani 1 1 d . . . . .
H13 H 1.096570 0.691857 0.997492 0.019 Uiso 1 1 calc R . . . .
C14 C 1.04234(18) 0.8818(2) 0.87299(15) 0.0155(3) Uani 1 1 d . . . . .
C15 C 0.91589(19) 0.8701(2) 0.82196(15) 0.0179(3) Uani 1 1 d . . . . .
H15 H 0.869019 0.973769 0.799119 0.021 Uiso 1 1 calc R . . . .
C16 C 0.84683(17) 0.7049(2) 0.79988(14) 0.0165(3) Uani 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 0.0181 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
C6 O2 C1 109.48(14) . . ?
C1 N1 C2 122.33(15) . . ?
C1 N1 C5 111.58(14) . . ?
C5 N1 C2 111.93(15) . . ?
O1 C1 O2 120.79(17) . . ?
O1 C1 N1 131.10(17) . . ?
N1 C1 O2 108.10(15) . . ?
N1 C2 C3 103.17(14) . . ?
C2 C3 C4 105.26(14) . . ?
C5 C4 C3 101.74(13) . . ?
N1 C5 C4 102.73(13) . . ?
N1 C5 C6 100.89(14) . . ?
C6 C5 C4 120.39(14) . . ?
O2 C6 C5 108.47(14) . . ?
C7 C6 O2 118.71(16) . . ?
C7 C6 C5 132.80(17) . . ?
C6 C7 C8 122.89(16) . . ?
O3 C8 O4 122.78(15) . . ?
O3 C8 C7 124.58(15) . . ?
O4 C8 C7 112.64(14) . . ?
C14 O6 C9 109.44(13) . . ?
C9 N2 C10 123.17(15) . . ?
C9 N2 C13 111.88(14) . . ?
C13 N2 C10 112.23(14) . . ?
O5 C9 O6 120.66(16) . . ?
O5 C9 N2 130.96(17) . . ?
N2 C9 O6 108.38(14) . . ?
N2 C10 C11 102.67(13) . . ?
C10 C11 C12 104.76(14) . . ?
C13 C12 C11 101.38(13) . . ?
N2 C13 C12 102.84(13) . . ?
N2 C13 C14 101.07(14) . . ?
C14 C13 C12 121.64(14) . . ?
O6 C14 C13 108.52(14) . . ?
C15 C14 O6 118.17(16) . . ?
C15 C14 C13 133.24(17) . . ?
C14 C15 C16 122.64(17) . . ?
O7 C16 O8 122.96(16) . . ?
O7 C16 C15 124.64(15) . . ?
O8 C16 C15 112.41(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 C1 1.202(2) . ?
O2 C1 1.403(2) . ?
O2 C6 1.374(2) . ?
O3 C8 1.229(2) . ?
O4 C8 1.325(2) . ?
N1 C1 1.339(3) . ?
N1 C2 1.477(2) . ?
N1 C5 1.468(2) . ?
C2 C3 1.536(3) . ?
C3 C4 1.540(2) . ?
C4 C5 1.528(2) . ?
C5 C6 1.503(2) . ?
C6 C7 1.332(3) . ?
C7 C8 1.454(2) . ?
O5 C9 1.202(2) . ?
O6 C9 1.401(2) . ?
O6 C14 1.377(2) . ?
O7 C16 1.230(2) . ?
O8 C16 1.325(2) . ?
N2 C9 1.342(2) . ?
N2 C10 1.478(2) . ?
N2 C13 1.465(2) . ?
C10 C11 1.529(3) . ?
C11 C12 1.534(2) . ?
C12 C13 1.533(2) . ?
C13 C14 1.502(2) . ?
C14 C15 1.334(2) . ?
C15 C16 1.455(3) . ?
