Catalyst-free synthesis of novel 1,5-benzodiazepines and 3,4-dihydroquinoxalines using isocyanide-based one-pot, three- and four-component reactions
Mohlala, Reagan L.; Coyanis, E. Mabel; Fernandes, Manuel A.; Bode, Moira L.; RSC Advances 11 (2021) 24466–24473; doi:10.1039/D1RA04444C

data_7243231
_publ_section_title
;
 Catalyst-free synthesis of novel 1,5-benzodiazepines and
 3,4-dihydroquinoxalines using isocyanide-based one-pot, three- and
 four-component reactions
;
_journal_issue                   39
_journal_name_full               'RSC Advances'
_journal_page_first              24466
_journal_page_last               24473
_journal_paper_doi               10.1039/D1RA04444C
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C18 H27 Cl2 N3'
_chemical_formula_sum            'C18 H27 Cl2 N3'
_chemical_formula_weight         356.32
_chemical_melting_point          418.0(10)
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-03 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1778(2)
_cell_length_b                   10.8600(3)
_cell_length_c                   21.2146(6)
_cell_measurement_reflns_used    7681
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.09
_cell_measurement_theta_min      2.67
_cell_volume                     1884.09(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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_temperature      173.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0462
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            36147
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         1.920
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0556 before and 0.0520 after correction. The Ratio of minimum to maximum transmission is 0.9466. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       blocky
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl-Acetate'
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.196
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1581 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0347P)^2^+0.0736P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0692
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3983
_reflns_number_total             4542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra04444c2.cif
_cod_data_source_block           CPMD11f_20m_mb4_cm2_dicl_0f
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '417-419' was changed to
'418.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7243231
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.912
_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:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              15575
_olex2_submission_special_instructions 'No special instructions were received'