Regio- and stereoselective synthesis of functionalized tetrahydro-benzochromenes and hexahydrochromenochromenones <i>via</i> [4 + 2] annulation of curcumins with nitrochromenes.
Laha, Banamali; Suresh, Alati; Namboothiri, Irishi N. N.; Organic & biomolecular chemistry 21 (2023) 1872–1877; doi:10.1039/d2ob02211g

data_7159153
_publ_section_title
;
 Regio- and stereoselective synthesis of functionalized
 tetrahydro-benzochromenes and hexahydrochromenochromenones <i>via</i> [4
 + 2] annulation of curcumins with nitrochromenes.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1872
_journal_page_last               1877
_journal_paper_doi               10.1039/d2ob02211g
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C34 H26 Br N O5'
_chemical_formula_sum            'C34 H26 Br N O5'
_chemical_formula_weight         608.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-27
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-09-14 deposited with the CCDC.	2023-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.667(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.6287(9)
_cell_length_b                   11.9136(7)
_cell_length_c                   12.2552(9)
_cell_measurement_reflns_used    1810
_cell_measurement_temperature    200(16)
_cell_measurement_theta_max      17.0870
_cell_measurement_theta_min      2.0900
_cell_volume                     1421.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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_environment      N~2~
_diffrn_ambient_temperature      200(16)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -100.81  15.69   0.50    2.00    --   -9.84 -59.25  20.08  233
  2  \w   -100.81  15.69   0.50    2.00    --   -9.84 -59.25 164.08  233
  3  \w   -100.81  15.69   0.50    2.00    --   -9.84 -59.25 -51.92  233
  4  \w   -100.81  15.69   0.50    2.00    --   -9.84 -59.25  92.08  233
  5  \f   -150.27  33.73   0.50    2.00  81.02  -9.84  31.50    --   368
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0415227000
_diffrn_orient_matrix_UB_12      0.0453784000
_diffrn_orient_matrix_UB_13      -0.0033181000
_diffrn_orient_matrix_UB_21      -0.0375585000
_diffrn_orient_matrix_UB_22      0.0370719000
_diffrn_orient_matrix_UB_23      0.0209315000
_diffrn_orient_matrix_UB_31      0.0465814000
_diffrn_orient_matrix_UB_32      -0.0105728000
_diffrn_orient_matrix_UB_33      0.0595710000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1093
_diffrn_reflns_av_unetI/netI     0.0916
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25964
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         1.814
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.490
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 997 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         4992
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0474
_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^)+(0.0167P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0886
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3014
_reflns_number_total             4992
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02211g3.cif
_cod_data_source_block           inn_bl_as_43_autored
_cod_depositor_comments
'Adding full bibliography for 7159152--7159153.cif.'
_cod_database_code               7159153
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNOBr
_reflns_odcompleteness_completeness 90.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.73
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008), C009(H009), C00E(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00L(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00I(H00I), C00N(H00N), C00P(H00P), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X),
 C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013),
 C014(H014), C015(H015)
2.d Idealised tetrahedral OH refined as rotating group:
 O005(H005)
;
_shelx_res_checksum              30591
_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 1.397
_oxdiff_exptl_absorpt_empirical_full_min 0.822