3-Nitro-3,4-dihydrocoumarins: Valuable precursors for the synthesis of enantiomerically enriched masked quaternary α-amino acid derivatives with a 3,4-dihydrocoumarin scaffold
Lv, Dan; Zhao, Min; Wang, Youming; Zhou, Zhenghong; Organic & Biomolecular Chemistry  (2019) –; doi:10.1039/C9OB02089F

data_7157162
_publ_section_title
;
 3-Nitro-3,4-dihydrocoumarins: Valuable precursors for the synthesis of
 enantiomerically enriched masked quaternary \a-amino acid derivatives
 with a 3,4-dihydrocoumarin scaffold
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/C9OB02089F
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H19 N O8'
_chemical_formula_sum            'C24 H19 N O8'
_chemical_formula_weight         449.40
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-24 deposited with the CCDC.    2019-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.31120(10)
_cell_length_b                   17.8036(2)
_cell_length_c                   30.2278(3)
_cell_measurement_reflns_used    26799
_cell_measurement_temperature    295.15
_cell_measurement_theta_max      78.3100
_cell_measurement_theta_min      2.9000
_cell_volume                     5549.11(10)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      295.15
_diffrn_detector                 PILT
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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    -84.00  40.00   0.50    4.00    --    5.00 -35.00-147.00  248
  2  \w   -138.00 -15.00   0.50    4.00    --  -49.50 -35.00-147.00  246
  3  \w   -199.00 -75.00   0.50   16.00    -- -110.00 -35.00-147.00  248
  4  \w   -145.00 -21.00   0.50   16.00    -- -110.00  35.00   9.00  248
  5  \w    -30.00  94.00   0.50    4.00    --    5.00  35.00   9.00  248
  6  \w    -82.00  39.00   0.50    4.00    --  -49.50  38.00 120.00  242
  7  \w   -138.00 -20.00   0.50    4.00    --  -49.50 -57.00  90.00  236
  8  \w   -143.00 -21.00   0.50   16.00    -- -110.00  38.00-150.00  244
  9  \w   -140.00 -21.00   0.50   16.00    -- -110.00  57.00   0.00  238
 10  \w   -143.00 -21.00   0.50   16.00    -- -110.00  38.00 -90.00  244
 11  \w   -140.00 -21.00   0.50   16.00    -- -110.00  57.00-150.00  238
 12  \w   -143.00 -21.00   0.50   16.00    -- -110.00  38.00 150.00  244
 13  \w   -136.00 -21.00   0.50   16.00    -- -110.00  72.00-150.00  230
 14  \w   -137.00 -56.00   0.50   16.00    -- -110.00  72.00   0.00  162
 15  \w    -83.00 -57.00   0.50   16.00    -- -110.00  57.00 -30.00   52
 16  \w   -132.00-105.00   0.50   16.00    -- -110.00  57.00 -30.00   54
 17  \w   -173.00 -78.00   0.50   16.00    -- -110.00 -38.00   0.00  190
 18  \w   -125.00 -99.00   0.50   16.00    -- -110.00  57.00-120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0249825000
_diffrn_orient_matrix_UB_12      0.0166003000
_diffrn_orient_matrix_UB_13      -0.0492934000
_diffrn_orient_matrix_UB_21      -0.0631864000
_diffrn_orient_matrix_UB_22      -0.0755096000
_diffrn_orient_matrix_UB_23      -0.0125422000
_diffrn_orient_matrix_UB_31      -0.1330088000
_diffrn_orient_matrix_UB_32      0.0389056000
_diffrn_orient_matrix_UB_33      -0.0032861000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            66075
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.464
_diffrn_reflns_theta_min         2.881
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60849
_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            white
_exptl_crystal_density_diffrn    1.076
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 4046 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_coef       0.00073(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     600
_refine_ls_number_reflns         11867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0445
_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/[\s^2^(Fo^2^)+(0.0865P)^2^+0.1568P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1372
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                10132
_reflns_number_total             11867
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02089f2.cif
_cod_data_source_block           p20180726a_sq
_cod_database_code               7157162
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C24H19NO8
_shelx_estimated_absorpt_t_max   0.922
_shelx_estimated_absorpt_t_min   0.841
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C40(H40), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C48(H48A,H48B), C7(H7A,H7B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C28(H28), C29(H29), C30(H30), C35(H35), C38(H38), C42(H42),
 C43(H43), C45(H45), C46(H46), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11),
 C14(H14), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C47(H47A,H47B,H47C), C23(H23A,H23B,H23C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O9(H9)
;
_shelx_res_checksum              42672
_shelx_hkl_checksum              90994
_shelx_fab_checksum              21844
_platon_squeeze_void_probe_radius 1.20
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.882
_oxdiff_exptl_absorpt_empirical_full_min 0.611