#------------------------------------------------------------------------------
#$Date: 2021-06-05 20:55:35 +0300 (Sat, 05 Jun 2021) $
#$Revision: 265918 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/03/1560312.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_1560312
loop_
_publ_author_name
'Mayer, Robert J.'
'Allihn, Patrick W. A.'
'Hampel, Nathalie'
'Mayer, Peter'
'Sieber, Stephan A.'
'Ofial, Armin R.'
_publ_section_title
;
 Electrophilic reactivities of cyclic enones and α,β-unsaturated
 lactones
;
_journal_issue                   13
_journal_name_full               'Chemical Science'
_journal_page_first              4850
_journal_page_last               4865
_journal_paper_doi               10.1039/D0SC06628A
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_chemical_name_common            RNH142F1
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_code                C14H13NO2_wv638_mayr
_audit_creation_method           'APEX3 v2017.3-0'
_audit_update_record
;
2020-11-13 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.797(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6656(4)
_cell_length_b                   9.4061(4)
_cell_length_c                   10.7626(5)
_cell_measurement_reflns_used    3795
_cell_measurement_temperature    112.(2)
_cell_measurement_theta_max      27.0609
_cell_measurement_theta_min      2.7920
_cell_volume                     1170.04(8)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2016.5-0, Bruker AXS (2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      112.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'fixed-chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture TXS'
_diffrn_measurement_method       'mix of phi and omega scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11194
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_min         3.246
_diffrn_source                   'rotating anode (TXS)'
_diffrn_source_current           50
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0434
_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)+(0.0360P)²+0.5952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1856
_reflns_number_total             2388
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc06628a2.cif
_cod_data_source_block           wv638
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

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

 Adding full bibliography for 1560309--1560315.cif.
;
_cod_database_code               1560312
_shelx_estimated_absorpt_t_min   0.993
_shelx_estimated_absorpt_t_max   0.997
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 -0.05132(10) 0.36380(13) 0.39951(11) 0.0268(3) Uani 1 1 d . . . . .
O2 O 0.02727(11) 0.52940(13) 0.29661(11) 0.0289(3) Uani 1 1 d . . . . .
N1 N 0.66389(13) 0.36602(18) 0.95272(14) 0.0318(4) Uani 1 1 d . . . . .
C1 C 0.15686(14) 0.35263(17) 0.39032(15) 0.0205(4) Uani 1 1 d . . . . .
C2 C 0.24985(15) 0.4006(2) 0.31534(16) 0.0255(4) Uani 1 1 d . . . . .
H2A H 0.311817 0.331844 0.303840 0.031 Uiso 1 1 calc R U . . .
H2B H 0.226531 0.463335 0.242449 0.031 Uiso 1 1 calc R U . . .
C3 C 0.24952(14) 0.46241(18) 0.44309(15) 0.0222(4) Uani 1 1 d . . . . .
H3 H 0.219949 0.562243 0.442147 0.027 Uiso 1 1 calc R U . . .
C4 C 0.04119(14) 0.42045(18) 0.35694(15) 0.0217(4) Uani 1 1 d . . . . .
C5 C 0.16002(14) 0.20441(17) 0.44420(16) 0.0227(4) Uani 1 1 d . . . . .
H5A H 0.238126 0.183476 0.488708 0.027 Uiso 1 1 calc R U . . .
H5B H 0.141863 0.133913 0.376066 0.027 Uiso 1 1 calc R U . . .
C6 C 0.07108(15) 0.19565(18) 0.53474(16) 0.0257(4) Uani 1 1 d . . . . .
H6A H 0.071592 0.099301 0.571842 0.031 Uiso 1 1 calc R U . . .
H6B H 0.090027 0.265174 0.603517 0.031 Uiso 1 1 calc R U . . .
C7 C -0.04614(15) 0.22745(18) 0.46444(17) 0.0278(4) Uani 1 1 d . . . . .
H7A H -0.067538 0.151045 0.402345 0.033 Uiso 1 1 calc R U . . .
H7B H -0.103721 0.227239 0.524069 0.033 Uiso 1 1 calc R U . . .
C8 C 0.33718(14) 0.42991(17) 0.55293(15) 0.0206(4) Uani 1 1 d . . . . .
C9 C 0.43804(15) 0.35389(18) 0.54323(16) 0.0247(4) Uani 1 1 d . . . . .
H9 H 0.449621 0.314697 0.464536 0.030 Uiso 1 1 calc R U . . .
C10 C 0.52159(15) 0.33433(18) 0.64571(16) 0.0242(4) Uani 1 1 d . . . . .
H10 H 0.590046 0.282517 0.637412 0.029 Uiso 1 1 calc R U . . .
C11 C 0.50463(14) 0.39121(17) 0.76127(15) 0.0210(4) Uani 1 1 d . . . . .
C12 C 0.40296(15) 0.46443(18) 0.77374(16) 0.0241(4) Uani 1 1 d . . . . .
H12 H 0.390563 0.501262 0.853016 0.029 Uiso 1 1 calc R U . . .
C13 C 0.32038(14) 0.48320(18) 0.67047(16) 0.0232(4) Uani 1 1 d . . . . .
H13 H 0.251119 0.533040 0.679320 0.028 Uiso 1 1 calc R U . . .
C14 C 0.59359(15) 0.37645(18) 0.86744(16) 0.0237(4) 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C7 122.09(13) . . ?
C4 C1 C2 115.89(14) . . ?
C4 C1 C5 117.51(14) . . ?
C2 C1 C5 120.06(14) . . ?
C4 C1 C3 111.55(14) . . ?
C2 C1 C3 58.56(11) . . ?
C5 C1 C3 119.78(14) . . ?
C3 C2 C1 62.06(11) . . ?
C3 C2 H2A 117.6 . . ?
C1 C2 H2A 117.6 . . ?
C3 C2 H2B 117.6 . . ?
C1 C2 H2B 117.6 . . ?
H2A C2 H2B 114.6 . . ?
C8 C3 C2 124.39(15) . . ?
C8 C3 C1 121.74(14) . . ?
C2 C3 C1 59.38(11) . . ?
C8 C3 H3 113.6 . . ?
C2 C3 H3 113.6 . . ?
C1 C3 H3 113.6 . . ?
O2 C4 O1 117.66(15) . . ?
O2 C4 C1 122.79(16) . . ?
O1 C4 C1 119.48(14) . . ?
C1 C5 C6 108.28(14) . . ?
C1 C5 H5A 110.0 . . ?
C6 C5 H5A 110.0 . . ?
C1 C5 H5B 110.0 . . ?
C6 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C7 C6 C5 108.71(14) . . ?
C7 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
C7 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
O1 C7 C6 113.13(14) . . ?
O1 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
O1 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 C13 118.37(15) . . ?
C9 C8 C3 122.89(15) . . ?
C13 C8 C3 118.68(15) . . ?
C10 C9 C8 121.34(16) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 119.44(16) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.12(15) . . ?
C10 C11 C14 119.76(15) . . ?
C12 C11 C14 120.11(15) . . ?
C13 C12 C11 119.74(15) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 120.95(16) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
N1 C14 C11 179.2(2) . . ?
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 C4 1.339(2) . ?
O1 C7 1.458(2) . ?
O2 C4 1.212(2) . ?
N1 C14 1.149(2) . ?
C1 C4 1.492(2) . ?
C1 C2 1.506(2) . ?
C1 C5 1.508(2) . ?
C1 C3 1.546(2) . ?
C2 C3 1.493(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C8 1.486(2) . ?
C3 H3 1.0000 . ?
C5 C6 1.519(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.500(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.393(2) . ?
C8 C13 1.399(2) . ?
C9 C10 1.382(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(2) . ?
C11 C14 1.442(2) . ?
C12 C13 1.380(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
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
C4 C1 C2 C3 100.48(16) . . . . ?
C5 C1 C2 C3 -108.59(17) . . . . ?
C1 C2 C3 C8 109.62(17) . . . . ?
C4 C1 C3 C8 138.08(16) . . . . ?
C2 C1 C3 C8 -113.93(18) . . . . ?
C5 C1 C3 C8 -4.9(2) . . . . ?
C4 C1 C3 C2 -107.99(16) . . . . ?
C5 C1 C3 C2 109.06(17) . . . . ?
C7 O1 C4 O2 175.09(15) . . . . ?
C7 O1 C4 C1 -8.0(2) . . . . ?
C2 C1 C4 O2 -17.2(2) . . . . ?
C5 C1 C4 O2 -168.85(15) . . . . ?
C3 C1 C4 O2 47.3(2) . . . . ?
C2 C1 C4 O1 166.06(14) . . . . ?
C5 C1 C4 O1 14.4(2) . . . . ?
C3 C1 C4 O1 -129.51(15) . . . . ?
C4 C1 C5 C6 -40.39(19) . . . . ?
C2 C1 C5 C6 169.13(14) . . . . ?
C3 C1 C5 C6 100.43(17) . . . . ?
C1 C5 C6 C7 59.85(18) . . . . ?
C4 O1 C7 C6 29.4(2) . . . . ?
C5 C6 C7 O1 -55.47(19) . . . . ?
C2 C3 C8 C9 9.5(2) . . . . ?
C1 C3 C8 C9 81.9(2) . . . . ?
C2 C3 C8 C13 -173.40(16) . . . . ?
C1 C3 C8 C13 -100.99(19) . . . . ?
C13 C8 C9 C10 -1.8(2) . . . . ?
C3 C8 C9 C10 175.30(16) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 1.4(2) . . . . ?
C9 C10 C11 C14 -177.37(16) . . . . ?
C10 C11 C12 C13 -1.5(2) . . . . ?
C14 C11 C12 C13 177.29(16) . . . . ?
C11 C12 C13 C8 -0.1(3) . . . . ?
C9 C8 C13 C12 1.7(2) . . . . ?
C3 C8 C13 C12 -175.50(15) . . . . ?
