#------------------------------------------------------------------------------
#$Date: 2016-03-24 00:12:42 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179527 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/24/4342472.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4342472
loop_
_publ_author_name
'Carpenter, Alex E.'
'Mokhtarzadeh, Charles C.'
'Ripatti, Donald S.'
'Havrylyuk, Irena'
'Kamezawa, Ryo'
'Moore, Curtis E.'
'Rheingold, Arnold L.'
'Figueroa, Joshua S.'
_publ_section_title
;
 Comparative measure of the electronic influence of highly substituted
 aryl isocyanides.
;
_journal_issue                   6
_journal_name_full               'Inorganic chemistry'
_journal_page_first              2936
_journal_page_last               2944
_journal_paper_doi               10.1021/ic5030845
_journal_volume                  54
_journal_year                    2015
_chemical_formula_moiety         'C26 H27 N'
_chemical_formula_sum            'C26 H27 N'
_chemical_formula_weight         353.48
_chemical_melting_point          ?
_chemical_name_common            CN(p-MeArMes2)
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-11-21
_audit_creation_method
; 
Olex2 1.2-beta 
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949) 
;
_cell_angle_alpha                90
_cell_angle_beta                 105.8060(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2227(8)
_cell_length_b                   10.1040(6)
_cell_length_c                   14.3484(8)
_cell_measurement_reflns_used    7776
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.45
_cell_volume                     2123.5(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (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    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX CCD'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15427
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.323
_diffrn_reflns_theta_min         2.449
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.0625 before and 0.0460 after correction. 
The Ratio of minimum to maximum transmission is 0.9327. 
The λ/2 correction factor is 0.0015. 
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2490
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0532P)²+1.4759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1167
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2226
_reflns_number_total             2490
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic5030845_si_002.cif
_cod_data_source_block           jfig464_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

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

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 4342470--4342481.cif.
;
_cod_database_code               4342472
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2014/6
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.5 times of: 
  All C(H,H,H) groups 
2. Others 
 Fixed Sof: H6A(0.5) H6B(0.5) H6C(0.5) 
3.a Idealised Me refined as rotating group: 
 C6(H6A,H6B,H6C), C12(H12A,H12B,H12C) 
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5000 0.11899(12) 0.7500 0.0236(3) Uani 1 2 d S T P . .
C1 C 0.5000 0.00477(17) 0.7500 0.0427(5) Uani 1 2 d S T P . .
C2 C 0.5000 0.25766(13) 0.7500 0.0198(3) Uani 1 2 d S T P . .
C3 C 0.54948(7) 0.32374(10) 0.69525(7) 0.0198(2) Uani 1 1 d . . . . .
C4 C 0.54824(7) 0.46163(10) 0.69637(7) 0.0223(2) Uani 1 1 d . . . . .
H4 H 0.5829(9) 0.5093(13) 0.6575(9) 0.026(3) Uiso 1 1 d . . . . .
C5 C 0.5000 0.53207(14) 0.7500 0.0224(3) Uani 1 2 d S T P . .
C6 C 0.5000 0.68075(15) 0.7500 0.0297(4) Uani 1 2 d S T P . .
H6A H 0.5630 0.7131 0.7706 0.045 Uiso 0.5 1 calc GR . . A -1
H6B H 0.4665 0.7131 0.7948 0.045 Uiso 0.5 1 calc GR . . A -1
H6C H 0.4705 0.7131 0.6846 0.045 Uiso 0.5 1 calc GR . . A -1
C7 C 0.60163(7) 0.24718(10) 0.63898(7) 0.0206(2) Uani 1 1 d . . . . .
C8 C 0.69422(7) 0.21917(11) 0.68068(8) 0.0259(2) Uani 1 1 d . . . . .
C9 C 0.74295(9) 0.26804(16) 0.78060(10) 0.0379(3) Uani 1 1 d . . . . .
H9A H 0.7560(14) 0.362(2) 0.7785(16) 0.076(6) Uiso 1 1 d . . . . .
H9B H 0.7064(13) 0.2562(19) 0.8280(14) 0.064(5) Uiso 1 1 d . . . . .
H9C H 0.8020(14) 0.2220(19) 0.8093(14) 0.066(5) Uiso 1 1 d . . . . .
C10 C 0.74093(8) 0.14475(12) 0.62774(9) 0.0300(3) Uani 1 1 d . . . . .
H10 H 0.8068(12) 0.1262(15) 0.6575(12) 0.045(4) Uiso 1 1 d . . . . .
C11 C 0.69860(8) 0.09856(11) 0.53534(9) 0.0289(3) Uani 1 1 d . . . . .
C12 C 0.75163(10) 0.01915(13) 0.47980(10) 0.0398(3) Uani 1 1 d . . . . .
H12A H 0.7684 -0.0666 0.5116 0.060 Uiso 1 1 calc GR . . . .
H12B H 0.8071 0.0675 0.4784 0.060 Uiso 1 1 calc GR . . . .
H12C H 0.7138 0.0051 0.4134 0.060 Uiso 1 1 calc GR . . . .
C13 C 0.60661(8) 0.12704(11) 0.49556(8) 0.0281(3) Uani 1 1 d . . . . .
H13 H 0.5744(10) 0.0943(14) 0.4290(11) 0.036(4) Uiso 1 1 d . . . . .
C14 C 0.55709(7) 0.20017(11) 0.54638(8) 0.0237(2) Uani 1 1 d . . . . .
C15 C 0.45699(8) 0.22693(13) 0.50187(9) 0.0317(3) Uani 1 1 d . . . . .
H15A H 0.4457(11) 0.3217(18) 0.4909(12) 0.047(4) Uiso 1 1 d . . . . .
H15B H 0.4192(12) 0.1970(17) 0.5445(12) 0.052(5) Uiso 1 1 d . . . . .
H15C H 0.4354(11) 0.1809(17) 0.4396(13) 0.047(4) Uiso 1 1 d . . . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C1 N1 C2 180.0 .
C3 C2 N1 118.55(6) 2_656
C3 C2 N1 118.55(6) .
C3 C2 C3 122.91(13) 2_656
C2 C3 C7 120.25(9) .
C4 C3 C2 117.40(9) .
C4 C3 C7 122.35(9) .
C3 C4 H4 118.0(8) .
C3 C4 C5 121.82(10) .
C5 C4 H4 120.2(8) .
C4 C5 C4 118.64(13) 2_656
C4 C5 C6 120.68(7) .
C4 C5 C6 120.68(7) 2_656
C5 C6 H6A 109.5 .
C5 C6 H6B 109.5 .
C5 C6 H6C 109.5 .
H6A C6 H6B 109.5 .
H6A C6 H6C 109.5 .
H6B C6 H6C 109.5 .
C8 C7 C3 119.64(9) .
C14 C7 C3 119.84(9) .
C14 C7 C8 120.48(10) .
C7 C8 C9 121.14(10) .
C10 C8 C7 118.63(10) .
C10 C8 C9 120.23(10) .
C8 C9 H9A 110.0(13) .
C8 C9 H9B 112.8(11) .
C8 C9 H9C 113.3(11) .
H9A C9 H9B 107.2(17) .
H9A C9 H9C 107.4(17) .
H9B C9 H9C 105.8(16) .
C8 C10 H10 118.2(9) .
C11 C10 C8 121.95(11) .
C11 C10 H10 119.9(9) .
C10 C11 C12 120.47(11) .
C10 C11 C13 118.43(10) .
C13 C11 C12 121.10(11) .
C11 C12 H12A 109.5 .
C11 C12 H12B 109.5 .
C11 C12 H12C 109.5 .
H12A C12 H12B 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C11 C13 H13 119.9(9) .
C11 C13 C14 121.48(10) .
C14 C13 H13 118.6(9) .
C7 C14 C15 120.89(10) .
C13 C14 C7 119.01(10) .
C13 C14 C15 120.10(10) .
C14 C15 H15A 110.9(10) .
C14 C15 H15B 111.9(10) .
C14 C15 H15C 110.5(10) .
H15A C15 H15B 106.9(14) .
H15A C15 H15C 108.5(14) .
H15B C15 H15C 108.0(14) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.154(2) .
N1 C2 1.4011(18) .
C2 C3 1.3973(12) .
C2 C3 1.3972(12) 2_656
C3 C4 1.3935(14) .
C3 C7 1.4933(13) .
C4 H4 0.990(13) .
C4 C5 1.3949(13) .
C5 C4 1.3949(13) 2_656
C5 C6 1.502(2) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C8 1.4019(15) .
C7 C14 1.4000(14) .
C8 C9 1.5067(16) .
C8 C10 1.3936(15) .
C9 H9A 0.97(2) .
C9 H9B 0.996(19) .
C9 H9C 1.00(2) .
C10 H10 0.995(17) .
C10 C11 1.3876(17) .
C11 C12 1.5103(15) .
C11 C13 1.3908(17) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13 1.004(15) .
C13 C14 1.3946(15) .
C14 C15 1.5076(16) .
C15 H15A 0.978(18) .
C15 H15B 0.994(17) .
C15 H15C 0.981(18) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N1 C2 C3 C4 179.90(6) . .
N1 C2 C3 C7 -0.54(10) . .
C2 C3 C4 C5 0.21(13) . .
C2 C3 C7 C8 -93.64(11) . .
C2 C3 C7 C14 84.25(11) . .
C3 C2 C3 C4 -0.10(6) 2_656 .
C3 C2 C3 C7 179.46(9) 2_656 .
C3 C4 C5 C4 -0.11(7) . 2_656
C3 C4 C5 C6 179.89(7) . .
C3 C7 C8 C9 -1.60(17) . .
C3 C7 C8 C10 178.41(10) . .
C3 C7 C14 C13 -178.98(9) . .
C3 C7 C14 C15 0.64(16) . .
C4 C3 C7 C8 85.90(13) . .
C4 C3 C7 C14 -96.21(12) . .
C7 C3 C4 C5 -179.35(8) . .
C7 C8 C10 C11 0.33(18) . .
C8 C7 C14 C13 -1.11(16) . .
C8 C7 C14 C15 178.51(10) . .
C8 C10 C11 C12 179.48(11) . .
C8 C10 C11 C13 -0.59(18) . .
C9 C8 C10 C11 -179.66(12) . .
C10 C11 C13 C14 0.00(17) . .
C11 C13 C14 C7 0.85(17) . .
C11 C13 C14 C15 -178.78(11) . .
C12 C11 C13 C14 179.93(11) . .
C14 C7 C8 C9 -179.47(11) . .
C14 C7 C8 C10 0.54(16) . .
