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_7132264
_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_formula_moiety         'C18 H14 N2 O2'
_chemical_formula_sum            'C18 H14 N2 O2'
_chemical_formula_weight         290.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-08
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6804)
;
_audit_update_record
;
2023-09-08 deposited with the CCDC.	2023-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                94.848(2)
_cell_angle_beta                 105.5620(10)
_cell_angle_gamma                90.870(2)
_cell_formula_units_Z            4
_cell_length_a                   8.8096(4)
_cell_length_b                   10.4907(5)
_cell_length_c                   16.2330(7)
_cell_measurement_reflns_used    7446
_cell_measurement_temperature    297.00
_cell_measurement_theta_max      23.44
_cell_measurement_theta_min      2.40
_cell_volume                     1438.95(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-III Photon II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            46378
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.170
_diffrn_reflns_theta_min         1.950
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1040 before and 0.0740 after correction.
The Ratio of minimum to maximum transmission is 0.7903.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.056
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         6389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0675
_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^)+(0.0873P)^2^+0.5454P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1766
_refine_ls_wR_factor_ref         0.2103
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3640
_reflns_number_total             6389
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04473d2.cif
_cod_data_source_block           mo_gs_rc_1_mi_2_0m
_cod_depositor_comments
;

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C36 H28 N4 O4'
_cod_original_formula_weight         580.62
_cod_original_formula_moiety         '2(C18 H14 N2 O2)'
_cod_original_formula_units_Z            2
_cod_database_code               7132264
_shelx_shelxl_version_number     2019/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C36(H36), C35(H35), C29(H29), C11(H11), C34(H34), C31(H31), C32(H32),
 C30(H30), C33(H33), C18(H18), C15(H15), C17(H17), C12(H12), C16(H16), C14(H14),
  C13(H13)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C19(H19A,H19B,H19C), C3(H3A,H3B,H3C), C1(H1A,H1B,H1C)
;
_shelx_res_checksum              76696
_shelx_hkl_checksum              9018
_olex2_exptl_crystal_mounting_method 'Nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'