Synthesis, Chemistry, and Photochemistry of Methylcyanobutadiyne in the Context of Space Science.
Kerisit, Nicolas; Rouxel, Cédric; Colombel-Rouen, Sophie; Toupet, Loïc; Guillemin, Jean-Claude; Trolez, Yann; The Journal of organic chemistry 81 (2016) 3560–3567; doi:10.1021/acs.joc.6b00205

data_4036650
_publ_section_title
;
 Synthesis, Chemistry, and Photochemistry of Methylcyanobutadiyne in the
 Context of Space Science.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3560
_journal_page_last               3567
_journal_paper_doi               10.1021/acs.joc.6b00205
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C10 H12 N2 O'
_chemical_formula_weight         176.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.3708(2)
_cell_length_b                   13.7544(5)
_cell_length_c                   15.5815(5)
_cell_measurement_reflns_used    2280
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.3970
_cell_measurement_theta_min      3.9420
_cell_volume                     936.72(6)
_computing_cell_refinement
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.37.35'
_computing_data_collection
'CrysAlis CCD, Oxford Diffraction Ltd.,Version 1.171.37.35'
_computing_data_reduction
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.37.35'
_computing_molecular_graphics    'MERCURY 3.3(CCDC, 2014)'
_computing_publication_material  'WINGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SIR-97_(Altomare & al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1852
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6662
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.987
_diffrn_reflns_theta_min         3.005
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31c (release 07-02-2014 CrysAlis171 .NET)
(compiled Feb  7 2014,14:07:06)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.151
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 672 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0428P)^2^+0.1533P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.664
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1851
_reflns_number_total             2050
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00205_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4036650
_shelxl_version_number           2014/6
_shelx_res_checksum              76703
_shelx_hkl_checksum              33960