#------------------------------------------------------------------------------
#$Date: 2021-01-07 06:30:26 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260599 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/73/7127336.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_7127336
loop_
_publ_author_name
'Mato, Raquel'
'Reyes, Efraim'
'Carrillo, Luisa'
'Uria, Uxue'
'Prieto, Liher'
'Manzano, Ruben'
'Vicario, Jose L.'
_publ_section_title
;
 Catalytic enantioselective domino Michael/transannular aldol reaction
 under bifunctional catalysis.
;
_journal_issue                   86
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              13149
_journal_page_last               13152
_journal_paper_doi               10.1039/d0cc05981a
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H21 N O4'
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_weight         315.36
_chemical_name_systematic
;
 (2S,2aS,2a1S,5aR)-5a-hydroxy-2-(methoxycarbonyl)-2a,2a1,3,4,5,5a,6,7-
octahydro-2H-benzo[6,7]cyclohepta[1,2,3-cd]isoindole 1-oxide
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-06-19T16:04:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-06-19 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.19139(11)
_cell_length_b                   11.21187(14)
_cell_length_c                   15.13619(18)
_cell_measurement_reflns_used    9239
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.13
_cell_measurement_theta_min      5.594
_cell_volume                     1559.82(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -131.00  37.00   1.00    1.00    --  -42.38   0.00-120.00  168
  2  ω     83.00 108.00   1.00    1.00    --   42.38 166.00-163.00   25
  3  ω     37.00  63.00   1.00    3.00    --  107.93 -30.00 150.00   26
  4  ω     35.00  69.00   1.00    3.00    --  107.93 -30.00  60.00   34
  5  ω     33.00  66.00   1.00    3.00    --  107.93 -30.00-150.00   33
  6  ω     82.00 156.00   1.00    3.00    --  107.93  61.00   0.00   74
  7  ω     33.00 103.00   1.00    3.00    --  107.93 -94.00 150.00   70
  8  ω     34.00  67.00   1.00    3.00    --  107.93 -30.00-180.00   33
  9  ω     43.00  92.00   1.00    3.00    --  107.93-125.00 120.00   49
 10  ω     79.00 153.00   1.00    3.00    --  107.93  77.00-120.00   74
 11  ω    -89.00 -15.00   1.00    1.00    --  -42.38 -51.00-168.00   74
 12  ω    -98.00 -33.00   1.00    1.00    --  -42.38 125.00 -60.00   65
 13  ω     34.00  70.00   1.00    1.00    --   42.38-125.00-180.00   36
 14  ω      4.00  36.00   1.00    1.00    --   42.38-125.00 120.00   32
 15  ω     41.00  67.00   1.00    3.00    --  107.93 -30.00   0.00   26
 16  ω     81.00 118.00   1.00    3.00    --  107.93  30.00 -30.00   37
 17  ω     36.00  62.00   1.00    3.00    --  107.93 -30.00  90.00   26
 18  ω     39.00  65.00   1.00    3.00    --  107.93 -30.00 -90.00   26
 19  ω     35.00  63.00   1.00    3.00    --  107.93 -30.00 120.00   28
 20  ω     47.00  81.00   1.00    3.00    --  107.93 -94.00  30.00   34
 21  ω     53.00  79.00   1.00    3.00    --  107.93 -61.00  60.00   26
 22  ω    104.00 132.00   1.00    3.00    --  107.93 -61.00  60.00   28
 23  ω     42.00 141.00   1.00    3.00    --  107.93 -77.00-150.00   99
 24  ω    129.00 155.00   1.00    3.00    --  107.93  30.00 -30.00   26
 25  ω     90.00 116.00   1.00    3.00    --  107.93-125.00 120.00   26
 26  ω     79.00 113.00   1.00    3.00    --  107.93-125.00 -90.00   34
 27  ω     87.00 130.00   1.00    3.00    --  107.93  61.00  60.00   43
 28  ω     36.00  69.00   1.00    3.00    --  107.93 -30.00 -30.00   33
 29  ω     83.00 110.00   1.00    3.00    --  107.93 -94.00 -60.00   27
 30  ω    -67.00  32.00   1.00    1.00    --  -42.38  38.00  30.00   99
 31  ω   -116.00 -14.00   1.00    1.00    --  -42.38 -57.00  90.00  102
 32  ω   -119.00 -10.00   1.00    1.00    --  -42.38 -77.00-150.00  109
 33  ω   -119.00 -10.00   1.00    1.00    --  -42.38 -77.00 -60.00  109
 34  ω      2.00  71.00   1.00    1.00    --   42.38-125.00 -90.00   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0295173
_diffrn_orient_matrix_UB_12      0.1350103
_diffrn_orient_matrix_UB_13      0.0063193
_diffrn_orient_matrix_UB_21      -0.1299989
_diffrn_orient_matrix_UB_22      0.0136756
_diffrn_orient_matrix_UB_23      0.0634675
_diffrn_orient_matrix_UB_31      0.1015605
_diffrn_orient_matrix_UB_32      -0.0217064
_diffrn_orient_matrix_UB_33      0.0793131
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16448
_diffrn_reflns_theta_full        74.42
_diffrn_reflns_theta_max         74.42
_diffrn_reflns_theta_min         4.91
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.82285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.03
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.13(16)
_refine_ls_extinction_coef       0.0009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0410P)²+0.1329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0751
_reflns_number_gt                2946
_reflns_number_total             3134
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0cc05981a2.cif
_cod_data_source_block           a20180380_rm998f1
_cod_depositor_comments
'Adding full bibliography for 7127335--7127336.cif.'
_cod_database_code               7127336
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.24394(13) 0.98837(9) 0.20230(6) 0.0311(2) Uani 1 d . .
O4 O 0.31713(11) 1.31551(10) 0.20395(7) 0.0343(3) Uani 1 d . .
O2 O 0.24751(12) 1.01159(11) 0.52349(6) 0.0358(3) Uani 1 d . .
H2 H 0.2604 1.0003 0.5764 0.054 Uiso 1 calc . .
N004 N 0.19653(12) 1.03444(10) 0.27545(7) 0.0220(2) Uani 1 d . .
C005 C 0.13489(14) 0.97997(12) 0.34259(8) 0.0211(3) Uani 1 d . .
C006 C 0.19277(16) 0.77237(13) 0.29545(10) 0.0291(3) Uani 1 d . .
H006 H 0.2582 0.8025 0.2542 0.035 Uiso 1 calc . .
C007 C 0.19442(14) 1.17643(11) 0.38682(8) 0.0208(3) Uani 1 d . .
H007 H 0.2904 1.156 0.4106 0.025 Uiso 1 calc . .
O3 O 0.46266(11) 1.17647(10) 0.26407(7) 0.0325(2) Uani 1 d . .
C009 C 0.01006(16) 0.80488(13) 0.40908(9) 0.0261(3) Uani 1 d . .
C010 C 0.20351(15) 1.16692(12) 0.28684(8) 0.0223(3) Uani 1 d . .
H010 H 0.1195 1.2054 0.259 0.027 Uiso 1 calc . .
C011 C 0.09124(15) 1.07390(11) 0.40953(8) 0.0203(3) Uani 1 d . .
H011 H -0.0083 1.0995 0.3961 0.024 Uiso 1 calc . .
C012 C 0.07845(18) 0.60469(14) 0.36486(12) 0.0393(4) Uani 1 d . .
H012 H 0.0674 0.5227 0.371 0.047 Uiso 1 calc . .
C013 C 0.11107(15) 0.85129(12) 0.34792(9) 0.0228(3) Uani 1 d . .
C014 C -0.00353(17) 0.68119(14) 0.41599(10) 0.0333(3) Uani 1 d . .
H014 H -0.0697 0.6495 0.4562 0.04 Uiso 1 calc . .
C015 C 0.34418(15) 1.21621(12) 0.24992(8) 0.0242(3) Uani 1 d . .
C016 C -0.0069(2) 0.94803(15) 0.53889(10) 0.0401(4) Uani 1 d . .
H01A H 0.0468 0.89 0.5735 0.048 Uiso 1 calc . .
H01B H -0.0785 0.9842 0.5776 0.048 Uiso 1 calc . .
C017 C -0.08723(18) 0.88194(14) 0.46545(10) 0.0340(3) Uani 1 d . .
H01C H -0.1619 0.8322 0.4918 0.041 Uiso 1 calc . .
H01D H -0.1353 0.9399 0.4279 0.041 Uiso 1 calc . .
C018 C 0.14693(16) 1.29167(12) 0.43014(10) 0.0286(3) Uani 1 d . .
H01E H 0.049 1.3123 0.4118 0.034 Uiso 1 calc . .
H01F H 0.2117 1.3562 0.4135 0.034 Uiso 1 calc . .
C019 C 0.17651(18) 0.64940(14) 0.30477(12) 0.0373(4) Uani 1 d . .
H019 H 0.2319 0.5977 0.2704 0.045 Uiso 1 calc . .
C020 C 0.15217(18) 1.27139(14) 0.53015(10) 0.0337(3) Uani 1 d . .
H02A H 0.2525 1.2605 0.5484 0.04 Uiso 1 calc . .
H02B H 0.1146 1.3415 0.56 0.04 Uiso 1 calc . .
C021 C 0.09998(16) 1.04594(13) 0.50855(8) 0.0244(3) Uani 1 d . .
C022 C 0.06346(15) 1.16265(13) 0.55780(9) 0.0274(3) Uani 1 d . .
H02C H -0.0388 1.1803 0.5488 0.033 Uiso 1 calc . .
H02D H 0.0778 1.1496 0.6206 0.033 Uiso 1 calc . .
C023 C 0.44392(19) 1.37884(15) 0.17088(12) 0.0403(4) Uani 1 d . .
H02E H 0.4132 1.4419 0.1323 0.06 Uiso 1 calc . .
H02F H 0.5051 1.3245 0.1389 0.06 Uiso 1 calc . .
H02G H 0.4972 1.4119 0.2196 0.06 Uiso 1 calc . .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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
C015 O4 C023 115.92(12) . . ?
O001 N004 C005 128.31(11) . . ?
O001 N004 C010 118.63(10) . . ?
C005 N004 C010 112.99(11) . . ?
N004 C005 C011 107.95(11) . . ?
N004 C005 C013 124.48(12) . . ?
C013 C005 C011 127.55(11) . . ?
C019 C006 C013 120.53(15) . . ?
C010 C007 C011 101.84(10) . . ?
C018 C007 C010 120.48(11) . . ?
C018 C007 C011 111.44(11) . . ?
C013 C009 C017 123.39(13) . . ?
C014 C009 C013 118.32(14) . . ?
C014 C009 C017 118.26(13) . . ?
N004 C010 C007 100.49(10) . . ?
N004 C010 C015 110.88(11) . . ?
C015 C010 C007 112.90(11) . . ?
C005 C011 C007 102.00(10) . . ?
C005 C011 C021 119.84(11) . . ?
C007 C011 C021 109.93(11) . . ?
C019 C012 C014 120.17(14) . . ?
C006 C013 C005 120.66(12) . . ?
C006 C013 C009 119.34(13) . . ?
C009 C013 C005 119.93(12) . . ?
C012 C014 C009 121.78(15) . . ?
O4 C015 C010 109.73(12) . . ?
O3 C015 O4 124.96(13) . . ?
O3 C015 C010 125.17(12) . . ?
C017 C016 C021 115.89(12) . . ?
C009 C017 C016 113.78(14) . . ?
C007 C018 C020 107.00(12) . . ?
C012 C019 C006 119.85(16) . . ?
C022 C020 C018 111.90(12) . . ?
O2 C021 C011 105.05(10) . . ?
O2 C021 C016 111.44(12) . . ?
O2 C021 C022 111.03(11) . . ?
C011 C021 C016 113.77(12) . . ?
C011 C021 C022 106.71(11) . . ?
C022 C021 C016 108.73(12) . . ?
C020 C022 C021 115.41(11) . . ?
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
O001 N004 1.2972(14) . ?
O4 C015 1.3364(17) . ?
O4 C023 1.4535(18) . ?
O2 C021 1.4276(17) . ?
N004 C005 1.3141(17) . ?
N004 C010 1.4967(16) . ?
C005 C011 1.5155(17) . ?
C005 C013 1.4615(18) . ?
C006 C013 1.406(2) . ?
C006 C019 1.394(2) . ?
C007 C010 1.5194(17) . ?
C007 C011 1.5294(18) . ?
C007 C018 1.5132(18) . ?
O3 C015 1.1959(17) . ?
C009 C013 1.4105(19) . ?
C009 C014 1.396(2) . ?
C009 C017 1.508(2) . ?
C010 C015 1.5131(19) . ?
C011 C021 1.5333(16) . ?
C012 C014 1.379(3) . ?
C012 C019 1.375(3) . ?
C016 C017 1.526(2) . ?
C016 C021 1.543(2) . ?
C018 C020 1.532(2) . ?
C020 C022 1.525(2) . ?
C021 C022 1.5430(19) . ?
