##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'PLATON <TABLE ACC> option'
_journal_date_recd_electronic     2019-01-15
_journal_date_accepted     2019-03-19
_journal_name_full     'IUCrData'
_journal_year     2019
_journal_volume     4
_journal_issue      4
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314619003766
_journal_coeditor_code     PK4023
_publ_contact_author_name
;
'Sundaramoorthy Gomathi'
;
_publ_contact_author_address
;
Periyar Maniammai University,
Thanjavur 613 403,
Tamil Nadu, India
;
_publ_contact_author_email     'gomathichemist@gmail.com'
_publ_contact_author_fax     '04362 264600'
_publ_contact_author_phone     '04362 264660'
_publ_section_title
;
1,3-Bis(2-cyanopropan-2-yl)-5-methylbenzene
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Gomathi, Sundaramoorthy' .
;
Department of Chemistry
Periyar Maniammai Institute of Science and Technology,
Thanjavur 613 403,
Tamil Nadu,
India
;
    'Sathya, Udhayasuriyan' .
;
Department of Chemistry
Periyar Maniammai Institute of Science and Technology,
Thanjavur 613 403,
Tamil Nadu,
India
;
    'Sharmila Tagore, Sadasivam' .
;
Department of Chemistry
Periyar Maniammai Institute of Science and Technology,
Thanjavur 613 403,
Tamil Nadu,
India
;
    'Nirmal Ram, Jeyaraman Selvaraj' .
;
Department of Chemistry,
PRIST Deemed to be University
Thanjavur 613 403,
Tamil Nadu,
India
;
    'Manikandan, Devakumar' .
;
Department of Chemistry
Periyar Maniammai Institute of Science and Technology,
Thanjavur 613 403,
Tamil Nadu,
India
;
    'Sethuraman, Velusamy' .
;
Department of Chemistry
Periyar Maniammai Institute of Science and Technology,
Thanjavur 613 403,
Tamil Nadu,
India
;
    'McMillen, Colin' .
;
Molecular Structure Center
Department of Chemistry
Clemson University
379 Hunter Laboratories
Clemson, SC 29634-0973
USA
;
_publ_section_synopsis
;
The crystal structure of the title compound has been characterized by
single-crystal X-ray diffraction and by IR, UV, and ¹H NMR spectroscopic
techniques. The molecule resides on a crystallographic twofold axis, which
leads to disorder of the H atoms on the methyl group attached to the benzene
ring.
;
data_I
_database_code_depnum_ccdc_archive 'CCDC 1904010'
_chemical_name_systematic
;
2,2'-(5-Methyl-1,3-phenylene)bis(2-methylpropanenitrile)
;
_chemical_name_common
;
1,3-Bis(2-cyanopropan-2-yl)-5-methylbenzene
;
_chemical_formula_moiety     'C15 H18 N2'
_chemical_formula_sum     'C15 H18 N2'
_chemical_formula_structural     ?
_chemical_formula_iupac     'C15 H18 N2'
_chemical_formula_weight     226.31
_chemical_melting_point     ?
_chemical_compound_source     'see text'
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _space_group_symop_id
    _space_group_symop_operation_xyz
    1 x,y,z
    2 -x,y,1/2-z
    3 -x,-y,-z
    4 x,-y,1/2+z
    5 1/2+x,1/2+y,z
    6 1/2-x,1/2+y,1/2-z
    7 1/2-x,1/2-y,-z
    8 1/2+x,1/2-y,1/2+z
_cell_length_a     13.821(6)
_cell_length_b     13.138(3)
_cell_length_c     9.473(3)
_cell_angle_alpha     90
_cell_angle_beta     126.133(8)
_cell_angle_gamma     90
_cell_volume     1389.3(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1261
_cell_measurement_theta_min     2.40
_cell_measurement_theta_max     25.20
_cell_measurement_temperature     298
_cell_special_details
;
;
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.520
_exptl_crystal_size_mid     0.240
_exptl_crystal_size_min     0.130
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.082
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     488
_exptl_absorpt_coefficient_mu     0.064
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrystalClear; Rigaku, 2008)
;
_exptl_absorpt_correction_T_min     0.653
_exptl_absorpt_correction_T_max     1.000
_exptl_special_details
;
;
_diffrn_ambient_temperature     298
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Sealed Tube'
_diffrn_radiation_monochromator     'Graphite Monochromator'
_diffrn_measurement_device_type
;
Rigaku Mercury
;
_diffrn_measurement_method     'dtprofit.ref'
_diffrn_detector_area_resol_mean     18.4
_diffrn_reflns_number     5988
_diffrn_reflns_av_R_equivalents     0.0433
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_theta_min     2.39
_diffrn_reflns_theta_max     25.25
_diffrn_reflns_theta_full     25.24
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_reflns_reduction_process
;
'Lp corrections applied'
;
_diffrn_radiation_probe     x-ray
_refine_special_details
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
All hydrogen atoms were positioned geometrically and were
refined using a riding model with C---H bond lengths 0.93--0.96 Å and with
Uiso(H) = 1.2Ueq(C) for CH (aromatic) or 1.5Ueq(C) for CH₃.
;
_reflns_number_total     1261
_reflns_number_gt     1012
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0718
_refine_ls_R_factor_gt     0.0585
_refine_ls_wR_factor_gt     0.1526
_refine_ls_wR_factor_ref     0.1680
_refine_ls_goodness_of_fit_ref     1.061
_refine_ls_restrained_S_all     1.061
_refine_ls_number_reflns     1261
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'w=1/[σ²(Fₒ²)+(0.0857P)²+0.6520P] where P=(Fₒ²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.182
_refine_diff_density_min     -0.136
_refine_ls_extinction_method     'none'
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0033 0.0016 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0.0000 0.0000 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0061 0.0033 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrystalClear (Rigaku, 2008)
;
_computing_cell_refinement
;
CrystalClear (Rigaku, 2008)
;
_computing_data_reduction
;
CrystalClear (Rigaku, 2008)
;
_computing_structure_solution
;
SHELXT2015 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2015 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009), Mercury (Macrae et al., 2008) and
POVRay (Cason, 2004)
;
_computing_publication_material
;
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N10 0.2028(3) 0.50771(16) 0.8107(5) 0.1065(13) Uani d . 1.000 . .
    C C1 0.07549(16) 0.16087(13) 0.7249(2) 0.0490(6) Uani d . 1.000 . .
    C C2 0.07652(15) 0.26634(13) 0.7246(2) 0.0427(5) Uani d . 1.000 . .
    C C3 0.00000 0.31872(17) 0.75000 0.0422(7) Uani d STP 1.000 . .
    C C4 0.00000 0.10686(19) 0.75000 0.0527(8) Uani d STP 1.000 . .
    C C5 0.15448(16) 0.32323(13) 0.6845(2) 0.0476(6) Uani d . 1.000 . .
    C C6 0.1794(2) 0.42686(15) 0.7556(3) 0.0646(8) Uani d . 1.000 . .
    C C7 0.00000 -0.0085(2) 0.75000 0.0781(13) Uani d STP 1.000 . .
    C C8 0.2775(2) 0.27308(17) 0.7686(3) 0.0678(8) Uani d . 1.000 . .
    C C9 0.0871(2) 0.3299(2) 0.4854(3) 0.0848(10) Uani d . 1.000 . .
    H H1 0.12620 0.12544 0.70811 0.0590 Uiso c RU 1.000 . .
    H H3 0.00000 0.38950 0.75000 0.0510 Uiso c RUP 1.000 . .
    H H7A -0.03430 -0.03284 0.80706 0.1170 Uiso c RUP 0.500 A -1
    H H7B 0.08078 -0.03284 0.81121 0.1170 Uiso c RUP 0.500 A -1
    H H7C -0.04647 -0.03284 0.63173 0.1170 Uiso c RUP 0.500 A -1
    H H8A 0.32525 0.31468 0.74812 0.1020 Uiso c RU 1.000 . .
    H H8B 0.26704 0.20704 0.71796 0.1020 Uiso c RU 1.000 . .
    H H8C 0.31717 0.26621 0.89209 0.1020 Uiso c RU 1.000 . .
    H H9A 0.01218 0.36436 0.43489 0.1270 Uiso c RU 1.000 . .
    H H9B 0.07231 0.26250 0.43753 0.1270 Uiso c RU 1.000 . .
    H H9C 0.13464 0.36694 0.45929 0.1270 Uiso c RU 1.000 . .
_geom_special_details
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N10 C6 . . 1.143(3) no
    C1 C2 . . 1.386(2) no
    C1 C4 . . 1.393(3) no
    C2 C3 . . 1.396(3) no
    C2 C5 . . 1.532(3) no
    C4 C7 . . 1.516(4) no
    C5 C6 . . 1.467(3) no
    C5 C8 . . 1.537(4) no
    C5 C9 . . 1.537(3) no
    C1 H1 . . 0.9300 no
    C3 H3 . . 0.9300 no
    C7 H7A . . 0.9600 no
    C7 H7B . . 0.9600 no
    C7 H7C . . 0.9600 no
    C7 H7A . 2_556 0.9600 no
    C7 H7B . 2_556 0.9600 no
    C7 H7C . 2_556 0.9600 no
    C8 H8A . . 0.9600 no
    C8 H8B . . 0.9600 no
    C8 H8C . . 0.9600 no
    C9 H9A . . 0.9600 no
    C9 H9B . . 0.9600 no
    C9 H9C . . 0.9600 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 C4 . . . 121.3(2) no
    C1 C2 C3 . . . 118.9(2) no
    C1 C2 C5 . . . 119.87(19) no
    C3 C2 C5 . . . 121.14(16) no
    C2 C3 C2 . . 2_556 120.95(19) no
    C1 C4 C7 . . . 120.62(12) no
    C1 C4 C1 . . 2_556 118.8(2) no
    C1 C4 C7 2_556 . . 120.62(12) no
    C2 C5 C6 . . . 110.37(19) no
    C2 C5 C8 . . . 112.78(16) no
    C2 C5 C9 . . . 109.05(18) no
    C6 C5 C8 . . . 105.75(19) no
    C6 C5 C9 . . . 108.60(17) no
    C8 C5 C9 . . . 110.2(2) no
    N10 C6 C5 . . . 177.2(4) no
    C2 C1 H1 . . . 119.00 no
    C4 C1 H1 . . . 119.00 no
    C2 C3 H3 . . . 120.00 no
    C2 C3 H3 2_556 . . 120.00 no
    C4 C7 H7A . . . 109.00 no
    C4 C7 H7B . . . 109.00 no
    C4 C7 H7C . . . 109.00 no
    C4 C7 H7A . . 2_556 109.00 no
    C4 C7 H7B . . 2_556 109.00 no
    C4 C7 H7C . . 2_556 109.00 no
    H7A C7 H7B . . . 109.00 no
    H7A C7 H7C . . . 109.00 no
    H7A C7 H7A . . 2_556 141.00 no
    H7A C7 H7B . . 2_556 56.00 no
    H7A C7 H7C . . 2_556 56.00 no
    H7B C7 H7C . . . 109.00 no
    H7A C7 H7B 2_556 . . 56.00 no
    H7B C7 H7B . . 2_556 141.00 no
    H7B C7 H7C . . 2_556 56.00 no
    H7A C7 H7C 2_556 . . 56.00 no
    H7B C7 H7C 2_556 . . 56.00 no
    H7C C7 H7C . . 2_556 141.00 no
    H7A C7 H7B 2_556 . 2_556 109.00 no
    H7A C7 H7C 2_556 . 2_556 109.00 no
    H7B C7 H7C 2_556 . 2_556 109.00 no
    C5 C8 H8A . . . 109.00 no
    C5 C8 H8B . . . 109.00 no
    C5 C8 H8C . . . 110.00 no
    H8A C8 H8B . . . 109.00 no
    H8A C8 H8C . . . 109.00 no
    H8B C8 H8C . . . 109.00 no
    C5 C9 H9A . . . 109.00 no
    C5 C9 H9B . . . 109.00 no
    C5 C9 H9C . . . 109.00 no
    H9A C9 H9B . . . 109.00 no
    H9A C9 H9C . . . 109.00 no
    H9B C9 H9C . . . 109.00 no
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C4 C1 C2 C3 . . . . 0.0(2) no
    C4 C1 C2 C5 . . . . -175.93(12) no
    C2 C1 C4 C7 . . . . -180.00(12) no
    C2 C1 C4 C1 . . . 2_556 0.00(17) no
    C1 C2 C3 C2 . . . 2_556 0.02(18) no
    C5 C2 C3 C2 . . . 2_556 175.86(12) no
    C1 C2 C5 C6 . . . . -157.97(17) no
    C1 C2 C5 C8 . . . . -40.0(2) no
    C1 C2 C5 C9 . . . . 82.8(2) no
    C3 C2 C5 C6 . . . . 26.2(2) no
    C3 C2 C5 C8 . . . . 144.25(15) no
    C3 C2 C5 C9 . . . . -92.99(19) no
