#------------------------------------------------------------------------------
#$Date: 2021-04-05 18:15:00 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263824 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/78/7157889.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_7157889
loop_
_publ_author_name
'Marquès, Clàudia'
'Diaba, Faïza'
'Roca, Jaume'
'Bonjoch, Josep'
_publ_section_title
;
 Synthesis and reactivity of hydroindole enelactams leading to densely
 functionalized scaffolds.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2284
_journal_page_last               2301
_journal_paper_doi               10.1039/d1ob00060h
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C21 H25 N O5'
_chemical_formula_sum            'C21 H25 N O5'
_chemical_formula_weight         371.42
_chemical_name_systematic        7a*
_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_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-11-30 deposited with the CCDC.	2021-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.255(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.443(3)
_cell_length_b                   7.818(3)
_cell_length_c                   29.113(11)
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.96
_cell_measurement_theta_min      2.97
_cell_volume                     1910.2(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            35945
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.572
_diffrn_reflns_theta_min         2.427
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_correction_T_min  0.6610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.608
_exptl_crystal_size_mid          0.314
_exptl_crystal_size_min          0.264
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         8666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0470
_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)+(0.0563P)²+0.6592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1356
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6865
_reflns_number_total             8666
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00060h2.cif
_cod_data_source_block           D43XB86_0m_a
_cod_depositor_comments
'Adding full bibliography for 7157888--7157889.cif.'
_cod_original_cell_volume        1910.3(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157889
_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.
;
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 0.78317(9) -0.00799(9) 0.46329(3) 0.02471(14) Uani 1 1 d . . . . .
O2 O 0.58632(9) 0.18395(9) 0.46875(3) 0.02340(14) Uani 1 1 d . . . . .
O3 O 1.18471(10) 0.50621(12) 0.43918(3) 0.03112(17) Uani 1 1 d . . . . .
O4 O 1.07551(8) 0.40195(9) 0.37084(2) 0.02050(13) Uani 1 1 d . . . . .
O5 O 0.89524(9) 0.78784(9) 0.34678(3) 0.02530(15) Uani 1 1 d . . . . .
N1 N 0.73706(9) 0.54662(10) 0.34416(3) 0.01931(14) Uani 1 1 d . . . . .
C1 C 0.71509(11) 0.14609(11) 0.44289(3) 0.01939(15) Uani 1 1 d . . . . .
C2 C 0.84144(10) 0.28848(11) 0.44690(3) 0.01860(15) Uani 1 1 d . . . . .
H2A H 0.871004 0.315559 0.479941 0.022 Uiso 1 1 calc R U . . .
H2AB H 0.938207 0.246932 0.434029 0.022 Uiso 1 1 calc R U . . .
C3 C 0.78222(10) 0.45184(11) 0.42131(3) 0.01688(14) Uani 1 1 d . . . . .
C4 C 0.71278(10) 0.40528(11) 0.37277(3) 0.01729(14) Uani 1 1 d . . . . .
C5 C 0.64725(11) 0.25536(12) 0.36002(3) 0.02058(16) Uani 1 1 d . . . . .
H5 H 0.597438 0.242006 0.329365 0.025 Uiso 1 1 calc R U . . .
C6 C 0.64999(12) 0.10628(12) 0.39292(3) 0.02336(17) Uani 1 1 d . . . . .
H6A H 0.715415 0.014039 0.381310 0.028 Uiso 1 1 calc R U . . .
H6AB H 0.540058 0.061994 0.392698 0.028 Uiso 1 1 calc R U . . .
C7 C 0.76531(14) 0.00075(15) 0.51179(4) 0.0291(2) Uani 1 1 d . . . . .
H7A H 0.868004 0.029170 0.529923 0.035 Uiso 1 1 calc R U . . .
H7AB H 0.726408 -0.109541 0.522946 0.035 Uiso 1 1 calc R U . . .
C8 C 0.64234(14) 0.14340(14) 0.51597(4) 0.0279(2) Uani 1 1 d . . . . .
H8A H 0.553952 0.102714 0.532873 0.033 Uiso 1 1 calc R U . . .
H8AB H 0.692452 0.244293 0.532172 0.033 Uiso 1 1 calc R U . . .
C9 C 0.91442(11) 0.58291(11) 0.41141(3) 0.01862(15) Uani 1 1 d . . . . .
H9 H 0.923735 0.675309 0.435303 0.022 Uiso 1 1 calc R U . . .
C10 C 0.85066(11) 0.65612(12) 0.36409(3) 0.01956(15) Uani 1 1 d . . . . .
C11 C 1.21996(12) 0.30239(14) 0.36721(4) 0.02525(18) Uani 1 1 d . . . . .
H11A H 1.249133 0.236872 0.395990 0.030 Uiso 1 1 calc R U . . .
H11B H 1.309654 0.379010 0.362017 0.030 Uiso 1 1 calc R U . . .
C12 C 1.07453(11) 0.49701(12) 0.40902(3) 0.01970(15) Uani 1 1 d . . . . .
C13 C 1.18473(16) 0.18289(17) 0.32703(5) 0.0372(3) Uani 1 1 d . . . . .
H13A H 1.151311 0.249101 0.299060 0.056 Uiso 1 1 calc R U . . .
H13B H 1.099174 0.104330 0.333251 0.056 Uiso 1 1 calc R U . . .
H13C H 1.280718 0.117233 0.322538 0.056 Uiso 1 1 calc R U . . .
C14 C 0.66975(11) 0.56006(14) 0.29610(3) 0.02235(17) Uani 1 1 d . . . . .
H14A H 0.692689 0.453310 0.279772 0.027 Uiso 1 1 calc R U . . .
H14B H 0.722568 0.655330 0.281341 0.027 Uiso 1 1 calc R U . . .
C15 C 0.49147(11) 0.59045(11) 0.29048(3) 0.01871(15) Uani 1 1 d . . . . .
C16 C 0.41864(11) 0.68882(12) 0.32239(3) 0.02151(16) Uani 1 1 d . . . . .
H16 H 0.481024 0.734915 0.348610 0.026 Uiso 1 1 calc R U . . .
C17 C 0.25513(12) 0.71963(13) 0.31594(4) 0.02376(17) Uani 1 1 d . . . . .
H17 H 0.206379 0.785259 0.337996 0.029 Uiso 1 1 calc R U . . .
C18 C 0.16307(12) 0.65463(14) 0.27734(4) 0.02700(19) Uani 1 1 d . . . . .
H18 H 0.051819 0.676743 0.272853 0.032 Uiso 1 1 calc R U . . .
C19 C 0.23433(13) 0.55732(16) 0.24538(4) 0.0293(2) Uani 1 1 d . . . . .
H19 H 0.171884 0.512977 0.218936 0.035 Uiso 1 1 calc R U . . .
C20 C 0.39783(13) 0.52466(14) 0.25213(3) 0.02436(18) Uani 1 1 d . . . . .
H20 H 0.445768 0.456883 0.230358 0.029 Uiso 1 1 calc R U . . .
C21 C 0.65725(12) 0.55084(12) 0.44615(3) 0.02170(16) Uani 1 1 d . . . . .
H21A H 0.631797 0.659123 0.430054 0.033 Uiso 1 1 calc R U . . .
H21B H 0.700638 0.574180 0.478136 0.033 Uiso 1 1 calc R U . . .
H21C H 0.560279 0.481839 0.445962 0.033 Uiso 1 1 calc R U . . .
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
C1 O1 C7 106.64(8) . . ?
C1 O2 C8 105.65(8) . . ?
C12 O4 C11 115.91(8) . . ?
C10 N1 C4 112.33(8) . . ?
C10 N1 C14 123.05(8) . . ?
C4 N1 C14 123.85(8) . . ?
O2 C1 O1 104.53(7) . . ?
O2 C1 C6 109.28(8) . . ?
O1 C1 C6 108.00(8) . . ?
O2 C1 C2 111.96(8) . . ?
O1 C1 C2 109.45(8) . . ?
C6 C1 C2 113.20(8) . . ?
C3 C2 C1 112.27(8) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2AB 109.2 . . ?
C1 C2 H2AB 109.2 . . ?
H2A C2 H2AB 107.9 . . ?
C4 C3 C2 109.00(7) . . ?
C4 C3 C21 109.97(7) . . ?
C2 C3 C21 113.06(7) . . ?
C4 C3 C9 101.35(7) . . ?
C2 C3 C9 115.67(7) . . ?
C21 C3 C9 107.12(7) . . ?
C5 C4 N1 127.36(8) . . ?
C5 C4 C3 125.36(8) . . ?
N1 C4 C3 107.23(7) . . ?
C4 C5 C6 121.76(8) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 115.21(8) . . ?
C5 C6 H6A 108.5 . . ?
C1 C6 H6A 108.5 . . ?
C5 C6 H6AB 108.5 . . ?
C1 C6 H6AB 108.5 . . ?
H6A C6 H6AB 107.5 . . ?
O1 C7 C8 104.85(8) . . ?
O1 C7 H7A 110.8 . . ?
C8 C7 H7A 110.8 . . ?
O1 C7 H7AB 110.8 . . ?
C8 C7 H7AB 110.8 . . ?
H7A C7 H7AB 108.9 . . ?
O2 C8 C7 103.80(8) . . ?
O2 C8 H8A 111.0 . . ?
C7 C8 H8A 111.0 . . ?
O2 C8 H8AB 111.0 . . ?
C7 C8 H8AB 111.0 . . ?
H8A C8 H8AB 109.0 . . ?
C12 C9 C10 110.56(7) . . ?
C12 C9 C3 112.05(8) . . ?
C10 C9 C3 102.84(7) . . ?
C12 C9 H9 110.4 . . ?
C10 C9 H9 110.4 . . ?
C3 C9 H9 110.4 . . ?
O5 C10 N1 125.83(9) . . ?
O5 C10 C9 126.17(9) . . ?
N1 C10 C9 107.99(8) . . ?
O4 C11 C13 106.97(9) . . ?
O4 C11 H11A 110.3 . . ?
C13 C11 H11A 110.3 . . ?
O4 C11 H11B 110.3 . . ?
C13 C11 H11B 110.3 . . ?
H11A C11 H11B 108.6 . . ?
O3 C12 O4 124.20(9) . . ?
O3 C12 C9 123.97(9) . . ?
O4 C12 C9 111.71(7) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 113.23(7) . . ?
N1 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
N1 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C20 C15 C16 118.86(9) . . ?
C20 C15 C14 119.91(8) . . ?
C16 C15 C14 121.20(8) . . ?
C17 C16 C15 120.42(9) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 120.24(9) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 119.78(10) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 119.98(10) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 120.72(9) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C3 C21 H21A 109.5 . . ?
C3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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 1.4352(12) . ?
O1 C7 1.4380(14) . ?
O2 C1 1.4195(12) . ?
O2 C8 1.4396(14) . ?
O3 C12 1.2097(12) . ?
O4 C12 1.3380(12) . ?
O4 C11 1.4603(12) . ?
O5 C10 1.2237(12) . ?
N1 C10 1.3668(13) . ?
N1 C4 1.4122(12) . ?
N1 C14 1.4554(13) . ?
C1 C6 1.5299(14) . ?
C1 C2 1.5375(13) . ?
C2 C3 1.5345(13) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.5141(13) . ?
C3 C21 1.5497(13) . ?
C3 C9 1.5650(13) . ?
C4 C5 1.3315(13) . ?
C5 C6 1.5072(14) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.5376(17) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C12 1.5178(14) . ?
C9 C10 1.5341(14) . ?
C9 H9 1.0000 . ?
C11 C13 1.5014(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.5150(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C20 1.3942(14) . ?
C15 C16 1.3988(13) . ?
C16 C17 1.3938(14) . ?
C16 H16 0.9500 . ?
C17 C18 1.3911(16) . ?
C17 H17 0.9500 . ?
C18 C19 1.3886(17) . ?
C18 H18 0.9500 . ?
C19 C20 1.3965(15) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
