The Application of 2-Benzyl-1,4-naphthoquinones as Pronucleophiles in Aminocatalytic Synthesis of Tricyclic Derivatives.
Skrzyńska, Anna; Romaniszyn, Marta; Pomikło, Dominika; Albrecht, Łukasz; The Journal of organic chemistry 83 (2018) 5019–5026; doi:10.1021/acs.joc.8b00170

data_4035516
_publ_section_title
;
 The Application of 2-Benzyl-1,4-naphthoquinones as Pronucleophiles in
 Aminocatalytic Synthesis of Tricyclic Derivatives.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5019
_journal_page_last               5026
_journal_paper_doi               10.1021/acs.joc.8b00170
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H17 Cl O2'
_chemical_formula_sum            'C26 H17 Cl O2'
_chemical_formula_weight         396.85
_chemical_name_systematic
(2R,3R)-3-(4-Chlorophenyl)-5-oxo-2-phenyl-3,5-dihydro-2H-cyclopenta[a]naphthalene-1-carbaldehyde
_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             2017-11-24
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.08.26 svn.r3337 for Rigaku Oxford Diffraction, GUI svn.r5221)
;
_audit_update_record
;
2017-11-24 deposited with the CCDC.
2017-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.9058(7)
_cell_length_b                   18.5704(12)
_cell_length_c                   31.694(4)
_cell_measurement_reflns_used    5617
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.0960
_cell_measurement_theta_min      3.6990
_cell_volume                     4064.5(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     57.00 114.00   0.50  100.00    --  105.75   0.00 150.00  114
  2  \w    -20.00  64.00   0.50   50.00    --    0.00  77.00-120.00  168
  3  \w    -49.00   8.00   0.50   50.00    --    0.00   0.00-180.00  114
  4  \w    -49.00   8.00   0.50   50.00    --    0.00   0.00 -60.00  114
  5  \w    -20.00  64.00   0.50   50.00    --    0.00  77.00 -60.00  168
  6  \w    -74.00   6.00   0.50   50.00    --    0.00 -38.00 120.00  160
  7  \w    -70.00  13.00   0.50   50.00    --    0.00 -57.00  30.00  166
  8  \w   -103.50 -84.00   0.50  100.00    --  -84.25 -57.00 150.00   39
  9  \w   -108.50 -79.00   0.50  100.00    --  -84.25 -19.00  30.00   59
 10  \w   -108.50 -79.00   0.50  100.00    --  -84.25 -19.00-180.00   59
 11  \w   -158.00 -78.00   0.50  100.00    --  -84.25 -38.00 -90.00  160
 12  \w     32.00  71.00   0.50  100.00    --  105.75 -38.00-150.00   78
 13  \w     32.00  71.00   0.50  100.00    --  105.75 -38.00-120.00   78
 14  \w     32.00  71.00   0.50  100.00    --  105.75 -38.00 -60.00   78
 15  \w     32.00  71.00   0.50  100.00    --  105.75 -38.00   0.00   78
 16  \w    -96.00 -14.00   0.50  100.00    --  -84.25  57.00-180.00  164
 17  \w   -133.00 -76.00   0.50  100.00    --  -84.25   0.00 -60.00  114
 18  \w   -104.00 -20.00   0.50  100.00    --  -84.25  77.00-180.00  168
 19  \w     38.00 111.00   0.50  100.00    --  105.75 -99.00  90.00  146
 20  \w     36.00 121.00   0.50  100.00    --  105.75-125.00  60.00  170
 21  \w     36.00 121.00   0.50  100.00    --  105.75-125.00 -90.00  170
 22  \w     38.00 111.00   0.50  100.00    --  105.75 -99.00 -30.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0273498000
_diffrn_orient_matrix_UB_12      0.0103629000
_diffrn_orient_matrix_UB_13      -0.0478184000
_diffrn_orient_matrix_UB_21      0.2215891000
_diffrn_orient_matrix_UB_22      0.0008656000
_diffrn_orient_matrix_UB_23      -0.0058863000
_diffrn_orient_matrix_UB_31      -0.0013044000
_diffrn_orient_matrix_UB_32      -0.0822980000
_diffrn_orient_matrix_UB_33      -0.0061124000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1522
_diffrn_reflns_av_unetI/netI     0.1424
_diffrn_reflns_Laue_measured_fraction_full 0.998
_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       18
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            38797
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.995
_diffrn_reflns_theta_min         3.667
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.810
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       needle
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.227
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 1251 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     582
_refine_ls_number_reflns         7379
_refine_ls_number_restraints     651
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.1321
_refine_ls_R_factor_gt           0.0639
_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/[\s^2^(Fo^2^)+(0.0730P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1682
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4252
_reflns_number_total             7379
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00170_si_002.cif
_cod_data_source_block           la_as-159x
_cod_database_code               4035516
_chemical_oxdiff_formula         'C20 H20 O2 Cl'
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
C27 \\sim C27A \\sim C28 \\sim O3 \\sim O3A: within 1.7A with sigma of 0.006
and sigma for terminal atoms of 0.01
C42A \\sim C41A \\sim C41 \\sim C46 \\sim C46A \\sim C45 \\sim C45A \\sim C44A
\\sim C44 \\sim C43 \\sim C43A \\sim C42: within 0.9A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Cl2 \\sim Cl2A: within 0.9A with sigma of 0.04 and sigma for terminal atoms of
0.08
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C27A)=Sof(H27A)=Sof(O3A)=1-FVAR(1)
 Sof(C27)=Sof(H27)=Sof(O3)=FVAR(1)
 Sof(H39A)=Sof(C41A)=Sof(C46A)=Sof(H46A)=Sof(C45A)=Sof(H45A)=Sof(C44A)=
 Sof(C43A)=Sof(H43A)=Sof(C42A)=Sof(H42A)=Sof(Cl2A)=1-FVAR(2)
 Sof(H39)=Sof(C41)=Sof(C46)=Sof(H46)=Sof(C45)=Sof(H45)=Sof(C44)=Sof(C43)=
 Sof(H43)=Sof(C42)=Sof(H42)=Sof(Cl2)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C39(H39), C39(H39A), C40(H40), C13(H13), C14(H14)
5.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C27A(H27A), C31(H31), C32(H32), C33(H33), C34(H34), C37(H37),
 C46(H46), C45(H45), C43(H43), C42(H42), C48(H48), C49(H49), C50(H50), C51(H51),
  C52(H52), C1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
  C46A(H46A), C45A(H45A), C43A(H43A), C42A(H42A)
5.c Fitted hexagon refined as free rotating group:
 C41(C46,C45,C44,C43,C42), C41A(C46A,C45A,C44A,C43A,C42A)
;
_shelx_res_checksum              75884
_shelx_hkl_checksum              97745
_shelx_fab_checksum              72397
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.011
_oxdiff_exptl_absorpt_empirical_full_min 0.342