Temperature-Controlled Divergent Hydroamination Cyclization [2+2]-Cycloaddition Cascade Reactions of Homopropargylic Amines with 2-Butynedioates: Direct Access To Pyrrolo- b-cyclobutene and Dihydro-1 H-azepines.
Li, Xinhong; Wang, Songmeng; Li, Shengli; Li, Kangming; Mo, Xin; Liu, Lingyan; Chang, Weixing; Li, Jing; The Journal of organic chemistry 84 (2019) 1288–1298; doi:10.1021/acs.joc.8b02730

data_4037551
_publ_section_title
;
 Temperature-Controlled Divergent Hydroamination Cyclization
 [2+2]-Cycloaddition Cascade Reactions of Homopropargylic Amines with
 2-Butynedioates: Direct Access To Pyrrolo- b-cyclobutene and Dihydro-1
 H-azepines.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1288
_journal_page_last               1298
_journal_paper_doi               10.1021/acs.joc.8b02730
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C22 H21 N O4'
_chemical_formula_weight         363.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/8
_cell_angle_alpha                90
_cell_angle_beta                 94.87(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9323(18)
_cell_length_b                   5.4480(11)
_cell_length_c                   38.734(8)
_cell_measurement_reflns_used    3363
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.7791
_cell_measurement_theta_min      2.3044
_cell_volume                     1878.1(7)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            11033
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         2.304
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0854
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1534P)^2^+0.6581P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2358
_refine_ls_wR_factor_ref         0.2588
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2523
_reflns_number_total             3245
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02730_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

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               4037551
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              29669
_shelx_hkl_checksum              91563