An expedient metal-free cascade route to chromonyl diene scaffolds: thermodynamic vs. kinetic control
Alizadeh, Abdolali; Bagherinejad, Akram; Kayanian, Jasmine; Vianello, Robert; RSC Advances 12 (2022) 34946–34950; doi:10.1039/D2RA05704B

data_7245984
_publ_section_title
;
 An expedient metal-free cascade route to chromonyl diene scaffolds:
 thermodynamic vs. kinetic control
;
_journal_issue                   54
_journal_name_full               'RSC Advances'
_journal_page_first              34946
_journal_page_last               34950
_journal_paper_doi               10.1039/D2RA05704B
_journal_volume                  12
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C27 H25 Cl N4 O4, H2 O'
_chemical_formula_sum            'C27 H27 Cl N4 O5'
_chemical_formula_weight         522.97
_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   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc24462l
_audit_creation_date             2019-11-05
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2019-12-05 deposited with the CCDC.	2022-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7052(19)
_cell_length_b                   13.015(3)
_cell_length_c                   19.712(4)
_cell_measurement_reflns_used    13987
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.1
_cell_volume                     2489.9(9)
_computing_cell_refinement       'Automar software package (3.3a, 2015)'
_computing_data_collection       'MAR345 dtb Program (1.24-4, 2013)'
_computing_data_reduction        'Automar software package (3.3a, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'PLATON (2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'image-plate detector'
_diffrn_detector_area_resol_mean 0.81
_diffrn_detector_type            MAR345-dtb
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'one-circle diffractometer'
_diffrn_measurement_device_type  MAR345
_diffrn_measurement_method       'image-plate detector - phi oscillation'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13987
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.066
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1.06285
_exptl_absorpt_correction_T_min  0.96275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'R.H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1574 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         4325
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0490
_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^)+(0.0534P)^2^+1.2688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1247
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                4148
_reflns_number_total             4325
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra05704b2.cif
_cod_data_source_block           2_pl
_cod_database_code               7245984
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.952
_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 H5B-N5
 0.87 with sigma of 0.02
 H1-O1
 0.82 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C13 \\sim C22 \\sim C26: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002 within 2A
4.a Free rotating group:
 O6(H6A,H6B)
4.b Rotating group:
 N3(H3A)
4.c Ternary CH refined with riding coordinates:
 C5(H5)
4.d Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C26(H26A,H26B)
4.e Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C14(H14), C16(H16), C18(H18), C19(H19), C23(H23), C24(H24)
4.f Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              34198
_submission_special_instructions 'No special instructions were received'