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_7159152
_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_formula_moiety         '0.5(C H Cl3), C36 H31 N O5'
_chemical_formula_sum            'C36.5 H31.5 Cl1.5 N O5'
_chemical_formula_weight         617.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-05
_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                 109.626(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.0341(5)
_cell_length_b                   12.7886(2)
_cell_length_c                   26.3878(6)
_cell_measurement_reflns_used    18945
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.4970
_cell_measurement_theta_min      1.7200
_cell_volume                     6685.9(3)
_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      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    -90.56 125.94   0.50    2.00  81.02  -9.84  31.50    --   433
  2  \f   -137.73  45.77   0.50    2.00   6.61  -9.84 -31.50    --   367
  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 -59.25-123.92  233
  5  \f   -127.92  55.58   0.50    2.00  15.81  -9.84 -59.25    --   367
;
_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      -0.0064381000
_diffrn_orient_matrix_UB_12      0.0215828000
_diffrn_orient_matrix_UB_13      -0.0259993000
_diffrn_orient_matrix_UB_21      0.0138366000
_diffrn_orient_matrix_UB_22      -0.0452822000
_diffrn_orient_matrix_UB_23      -0.0078248000
_diffrn_orient_matrix_UB_31      -0.0323905000
_diffrn_orient_matrix_UB_32      -0.0236719000
_diffrn_orient_matrix_UB_33      -0.0087742000
_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  0.0664
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            150854
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.514
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51937
_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_density_diffrn    1.227
_exptl_crystal_description       block
_exptl_crystal_F_000             2584
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     797
_refine_ls_number_reflns         11768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0710
_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^)+(0.1409P)^2^+6.3006P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2077
_refine_ls_wR_factor_ref         0.2252
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9161
_reflns_number_total             11768
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02211g3.cif
_cod_data_source_block           inn_bl_as_134_autored
_cod_depositor_comments
;

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C73 H63 Cl3 N2 O10'
_cod_original_formula_weight         1234.60
_cod_original_formula_moiety         'C H Cl3, 2(C36 H31 N O5), 1[CHCl3]'
_cod_original_formula_units_Z            4
_cod_database_code               7159152
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 91.00
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00H(H00H), C00K(H00K), C00P(H00P), C00T(H00T), C00W(H00W), C00Y(H00Y),
 C011(H011), C01E(H01I), C02G(H02P)
2.b Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B), C010(H01F,H01H), C013(H01A,H01B), C01N(H01S,H01W)
2.c Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00R(H00R), C015(H015), C01A(H01C), C01B(H01D), C01C(H01E),
 C01G(H01G), C01H(H01J), C01I(H01K), C01J(H01N), C01K(H01O), C01L(H01L),
 C01M(H01M), C01P(H01P), C01Q(H01Q), C01R(H01R), C01S(H01X), C01T(H01T),
 C01U(H01U), C01V(H01V), C01W(H01Y), C01X(H01), C01Z(H01Z), C020(H020),
 C022(H022), C023(H023), C024(H024), C025(H025), C027(H027), C028(H028),
 C029(H029), C02A(H02K), C02B(H02D), C02E(H02L)
2.d Idealised Me refined as rotating group:
 C021(H02A,H02B,H02C), C026(H02H,H02I,H02J), C02D(H02E,H02F,H02G), C02F(H02M,
 H02N,H02O)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              5488
_shelx_fab_checksum              82447
_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 1.393
_oxdiff_exptl_absorpt_empirical_full_min 0.647