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_7154350
_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 H8 Br F3 N2 O3'
_chemical_formula_sum            'C12 H8 Br F3 N2 O3'
_chemical_formula_weight         365.10
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-03
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.10.30 svn.r3070 for OlexSys, GUI svn.r4932)
;
_audit_update_record
;
2014-12-15 deposited with the CCDC.
2015-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                102.643(3)
_cell_angle_beta                 91.759(3)
_cell_angle_gamma                104.107(3)
_cell_formula_units_Z            2
_cell_length_a                   6.79290(10)
_cell_length_b                   9.5186(2)
_cell_length_c                   10.3220(2)
_cell_measurement_reflns_used    8948
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.587
_cell_measurement_theta_min      2.269
_cell_volume                     629.09(2)
_computing_cell_refinement       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  '3-circle diffractometer'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10397
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.27
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    3.321
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4928
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1521 before and 0.1023 after correction.
The Ratio of minimum to maximum transmission is 0.4928.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.927
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.424
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.187
_refine_diff_density_max         1.843
_refine_diff_density_min         -0.993
_refine_diff_density_rms         0.226
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0900P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                2835
_reflns_number_total             3027
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00245a3.cif
_cod_data_source_block           14srv235
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3086 2015-02-26 13:12:21Z robertas 

 Adding full bibliography for 7154349--7154352.cif.
;
_cod_database_code               7154350
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_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:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'