Flow synthesis of ethyl isocyanoacetate enabling the telescoped synthesis of 1,2,4-triazoles and pyrrolo-[1,2-c]pyrimidines.
Baumann, Marcus; Rodriguez Garcia, Antonio M.; Baxendale, Ian R.; Organic & biomolecular chemistry 13 (2015) 4231–4239; doi:10.1039/c5ob00245a

data_7154349
_publ_section_title
;
 Flow synthesis of ethyl isocyanoacetate enabling the telescoped synthesis
 of 1,2,4-triazoles and pyrrolo-[1,2-c]pyrimidines.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4231
_journal_page_last               4239
_journal_paper_doi               10.1039/c5ob00245a
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C12 H9 F3 N2 O3'
_chemical_formula_sum            'C12 H9 F3 N2 O3'
_chemical_formula_weight         286.21
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-12-12
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2014-12-15 deposited with the CCDC.
2015-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   12.5161(10)
_cell_length_b                   14.0082(11)
_cell_length_c                   27.051(2)
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.91
_cell_measurement_theta_min      2.309
_cell_volume                     4742.8(6)
_computing_cell_refinement       'SAINT v7.46A (Bruker, 2008)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-2012 (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            37987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.506
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2009/1 (Bruker,2010) was used for absorption correction.
wR2(int) was 0.0900 before and 0.0582 after correction.
The Ratio of minimum to maximum transmission is 0.8164.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       brick
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4178
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.209
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0665
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+12.3320P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.1646
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3538
_reflns_number_total             4178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00245a3.cif
_cod_data_source_block           13srv320
_cod_depositor_comments
'Adding full bibliography for 7154349--7154352.cif.'
_cod_original_cell_volume        4742.7(7)
_cod_database_code               7154349
_shelxl_version_number           2013-2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Uiso(H12A)=Uiso(H12B)=Uiso(H12C)=FVAR(1)
 Uiso(H12D)=Uiso(H12E)=Uiso(H12F)=FVAR(2)
3.a Rotating group:
 C12A(H12A,H12B,H12C), C12B(H12D,H12E,H12F)
3.b Secondary CH2 refined with riding coordinates:
 C11A(H11A,H11B), C11B(H11C,H11D)
3.c Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C5A(H5A), C7A(H7A), C10A(H10A), C4B(H4B), C5B(H5B), C7B(H7B),
 C10B(H10B)
;