Synthesis of <i>N</i>-Pyrrolyl(furanyl)-Substituted Piperazines, 1,4-Dizepanes, and 1,4-Diazocanes.
Mittersteiner, Mateus; Andrade, Valquiria P.; Zachow, Lucimara L.; Frizzo, Clarissa P.; Bonacorso, Helio G.; Martins, Marcos A. P.; Zanatta, Nilo; The Journal of organic chemistry 84 (2019) 8976–8983; doi:10.1021/acs.joc.9b00867

data_4034202
_publ_section_title
;
 Synthesis of <i>N</i>-Pyrrolyl(furanyl)-Substituted Piperazines,
 1,4-Dizepanes, and 1,4-Diazocanes.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8976
_journal_page_last               8983
_journal_paper_doi               10.1021/acs.joc.9b00867
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C14 H14 F6 N2 O2'
_chemical_formula_sum            'C14 H14 F6 N2 O2'
_chemical_formula_weight         356.27
_chemical_melting_point          ?
_chemical_name_common            Propanona
_chemical_name_systematic
;
'(Z)-1,1,1-trifluoro-3-(4-(5-trifluorometil)furan-3-il)-1,4-diazocan-2-ilideno)p
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2018-03-23T16:16:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 94.423(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1554(4)
_cell_length_b                   5.0593(2)
_cell_length_c                   29.8899(12)
_cell_measurement_reflns_used    5052
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      67.31
_cell_measurement_theta_min      2.97
_cell_measurement_wavelength     1.54178
_cell_volume                     1531.15(11)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER APEX-III'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker D8 Quest Photon 100 diffractometer'
_diffrn_measurement_method       '2\% \f & \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            18097
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.427
_diffrn_reflns_theta_min         2.966
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.361
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6893
_exptl_absorpt_correction_type   &#x0091;Multi-scan&#x0092;
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.194
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.178
_exptl_transmission_factor_max   none
_exptl_transmission_factor_min   none
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     249
_refine_ls_number_reflns         2716
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0944
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1804P)^2^+0.7738P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2571
_refine_ls_wR_factor_ref         0.2919
_reflns_Friedel_coverage         0
_reflns_number_gt                1776
_reflns_number_total             2716
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00867_si_003.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'none' was changed to '?'
-- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034202
_shelx_estimated_absorpt_t_min   0.778
_shelx_estimated_absorpt_t_max   0.794