Design and synthesis of 1,2-dihydroquinoline/chromene fused sugar triazole frameworks by copper-catalyzed one-pot click and intramolecular arylation reactions.
Ahemad, Mohammed Ansar; Nayak, Sabita; Prusty, Kamalika; Panigrahi, Gopinatha; Mohapatra, Suhasini; Mohapatra, Seetaram; Organic & biomolecular chemistry 22 (2024) 6748–6762; doi:10.1039/d4ob00711e

data_7160082
_publ_section_title
;
 Design and synthesis of 1,2-dihydroquinoline/chromene fused sugar
 triazole frameworks by copper-catalyzed one-pot click and intramolecular
 arylation reactions.
;
_journal_issue                   33
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6748
_journal_page_last               6762
_journal_paper_doi               10.1039/d4ob00711e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C28 H27 N3 O5'
_chemical_formula_sum            'C28 H27 N3 O5'
_chemical_formula_weight         485.52
_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   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2jcqd1
_audit_creation_date             2024-02-23
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-02-23 deposited with the CCDC.	2024-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4997(8)
_cell_length_b                   9.6206(9)
_cell_length_c                   27.309(3)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.317
_cell_measurement_theta_min      2.244
_cell_volume                     2495.8(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_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  0.0464
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            51312
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.897
_diffrn_reflns_theta_min         2.244
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6624
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1288 before and 0.0585 after correction.
The Ratio of minimum to maximum transmission is 0.8882.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       needle
_exptl_crystal_F_000             1024
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 1977 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         6535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0401P)^2^+0.3583P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1025
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                5379
_reflns_number_total             6535
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00711e2.cif
_cod_data_source_block           maa_270_p_0m
_cod_depositor_comments          'Adding full bibliography for 7160082.cif.'
_cod_original_cell_volume        2495.9(4)
_cod_database_code               7160082
_shelx_shelxl_version_number     2018/3
_exptl_absorpt_special_details   needle
_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:
 C009(H009), C00D(H00D), C00H(H00H), C00L(H00L)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B), C00I(H00E,H00F), C00S(H00G,H00I)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00J(H00J), C00P(H00P), C00Q(H00Q), C00R(H00R), C00T(H00T),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C010(H010)
2.d Idealised Me refined as rotating group:
 C00U(H00K,H00M,H00N), C00Z(H00O,H00S,H00U)
;
_shelx_res_checksum              22639
_olex2_submission_special_instructions 'No special instructions were received'