Transition Metal-Free and Temperature Dependent One-Pot Access to Phenanthrene-Fused Heterocycles via 1,3-Dipolar Cycloaddition Pathway
Reddy, Mokilla Ramachandra; Eerappa , Rajakumara; Gedu, Satyanarayana; Chemical Communications  (2023) –; doi:10.1039/D3CC04473D

data_7132262
_publ_section_title
;
 Transition Metal-Free and Temperature Dependent One-Pot Access to
 Phenanthrene-Fused Heterocycles via 1,3-Dipolar Cycloaddition Pathway
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04473D
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H22 N2 O4'
_chemical_formula_sum            'C26 H22 N2 O4'
_chemical_formula_weight         426.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-09-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-09-08 deposited with the CCDC.	2023-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.324(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0990(9)
_cell_length_b                   16.0302(11)
_cell_length_c                   10.1789(6)
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.26
_cell_measurement_theta_min      2.54
_cell_volume                     2137.3(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21424
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.292
_diffrn_reflns_theta_min         2.541
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1128 before and 0.0590 after correction.
The Ratio of minimum to maximum transmission is 0.8740.
The \l/2 correction factor is Not present.
;
_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    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_preparation       'In DCM and hexane'
_exptl_crystal_recrystallization_method DCM/Hexane
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4684
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0461P)^2^+0.2303P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0912
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4010
_reflns_number_total             4684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04473d2.cif
_cod_data_source_block           3ea
_cod_database_code               7132262
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.940
_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 Secondary CH2 refined with riding coordinates:
 C24(H24a,H24b)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C8(H8), C11(H11), C15(H15), C16(H16), C17(H17),
 C18(H18), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C25(H25a,H25b,H25c), C26(H26a,H26b,H26c)
;
_shelx_res_checksum              35380
_shelx_hkl_checksum              9750
_olex2_exptl_crystal_mounting_method 'Mounted on nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'