Microwave irradiation: a green approach for the synthesis of functionalized N-methyl-1,4-dihydropyridines
Khan, M. Musawwer; Saigal, Saigal; Khan, Sarfaraz; Shareef, Sumbulunnisan; Sahoo, Subash C.; RSC Advances 8 (2018) 41892–; doi:10.1039/C8RA09155B

data_7232003
_publ_section_title
;
 Microwave irradiation: a green approach for the synthesis of
 functionalized N-methyl-1,4-dihydropyridines
;
_journal_issue                   73
_journal_name_full               'RSC Advances'
_journal_page_first              41892
_journal_paper_doi               10.1039/C8RA09155B
_journal_volume                  8
_journal_year                    2018
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C15 H18 N4 O4 S'
_chemical_formula_sum            'C15 H18 N4 O4 S'
_chemical_formula_weight         350.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-20
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_audit_update_record
;
2018-05-04 deposited with the CCDC.
2018-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                104.253(4)
_cell_angle_beta                 90.749(3)
_cell_angle_gamma                111.461(5)
_cell_formula_units_Z            2
_cell_length_a                   7.3596(3)
_cell_length_b                   9.2464(6)
_cell_length_c                   14.1726(5)
_cell_measurement_reflns_used    7508
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.2190
_cell_measurement_theta_min      3.5210
_cell_volume                     864.24(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -48.00 -15.00   0.50    8.00    --   -9.95 111.00 171.00   66
  2  \w     -7.00  40.00   0.50    8.00    --   10.22-111.00  77.00   94
  3  \w    -56.00 -31.00   0.50    8.00    --   -9.95 125.00  30.00   50
  4  \w      7.00  48.00   0.50    8.00    --   -9.95  57.00   0.00   82
  5  \w    -50.00 -24.00   0.50    8.00    --   -9.95 125.00-180.00   52
  6  \w    -25.00   1.00   0.50    8.00    --   -9.95  57.00   0.00   52
  7  \w    -21.00   4.00   0.50    8.00    --   -9.95 -38.00 150.00   50
  8  \w    -74.00 -45.00   0.50    8.00    --   -9.95 -38.00 150.00   58
  9  \w    -61.00   2.00   0.50    8.00    --   -9.95 -19.00 150.00  126
 10  \w    -70.00   2.00   0.50    8.00    --   -9.95 -38.00  60.00  144
 11  \w    -54.00 -23.00   0.50    8.00    --   10.22 -77.00   0.00   62
 12  \w      5.00  59.00   0.50    8.00    --   10.22-125.00 -30.00  108
 13  \w    -32.00  -2.00   0.50    8.00    --   10.22 123.00-169.37   60
 14  \w    -52.00  11.00   0.50    8.00    --   10.22 -19.00  60.00  126
 15  \w    -33.00  -1.00   0.50    8.00    --   10.22 122.00  20.61   64
 16  \w      3.00  53.00   0.50    8.00    --   10.22-125.00-180.00  100
 17  \w     -2.00  23.00   0.50    8.00    --   10.22 -77.00   0.00   50
 18  \w     -1.00  74.00   0.50    8.00    --   10.22  38.00   0.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0300041000
_diffrn_orient_matrix_UB_12      0.0559970000
_diffrn_orient_matrix_UB_13      -0.0285963000
_diffrn_orient_matrix_UB_21      0.0559152000
_diffrn_orient_matrix_UB_22      0.0613419000
_diffrn_orient_matrix_UB_23      0.0420917000
_diffrn_orient_matrix_UB_31      0.0827003000
_diffrn_orient_matrix_UB_32      -0.0207010000
_diffrn_orient_matrix_UB_33      -0.0105925000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11900
_diffrn_reflns_theta_full        27.3645
_diffrn_reflns_theta_max         27.06
_diffrn_reflns_theta_min         3.19
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light yellow'
_exptl_crystal_density_diffrn    1.3464
_exptl_crystal_description       block
_exptl_crystal_F_000             368.4235
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.2638
_refine_diff_density_min         -0.2584
_refine_diff_density_rms         0.0517
_refine_ls_d_res_high            0.7731
_refine_ls_d_res_low             6.3881
_refine_ls_goodness_of_fit_ref   1.0504
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0504
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0763P)^2^+0.1314P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1447
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2796
_reflns_number_total             3695
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8ra09155b2.cif
_cod_data_source_block           musa-NM92
_cod_database_code               7232003
_chemical_oxdiff_formula         'C H N O '
_diffrn_oxdiff_ac3_digest_frames
;
010ec378803486451121739d89fe0ce42400025f1b3
;
_diffrn_oxdiff_ac3_digest_hkl
;
01d78d6236c48a65027267f331396291a2fe33
;
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00E(H00E)
2.b Aromatic/amide H refined with riding coordinates:
 N007(H007), C00G(H00G), C00L(H00L), C00M(H00M), C00N(H00N)
2.c Idealised Me refined as rotating group:
 C00H(H00a,H00b,H00c), C00J(H00d,H00f,H00h), C00K(H00i,H00j,H00k), C00O(H00o,
 H00p,H00q)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.833
_oxdiff_exptl_absorpt_empirical_full_min 0.477