#------------------------------------------------------------------------------
#$Date: 2017-09-12 06:55:41 +0300 (Tue, 12 Sep 2017) $
#$Revision: 200710 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/25/4032558.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_4032558
loop_
_publ_author_name
'Peterson, Joshua P.'
'Geraskina, Margarita R.'
'Zhang, Rui'
'Winter, Arthur H.'
_publ_section_title
;
 Effect of Substituents on the Bond Strength of Air-Stable Dicyanomethyl
 Radical Thermochromes.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6497
_journal_page_last               6501
_journal_paper_doi               10.1021/acs.joc.7b01188
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C11 H11 N3'
_chemical_formula_weight         185.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 96.34(3)
_cell_angle_gamma                90.00(3)
_cell_formula_units_Z            4
_cell_length_a                   8.032(2)
_cell_length_b                   6.421(2)
_cell_length_c                   19.345(4)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      68.2113
_cell_measurement_theta_min      4.5972
_cell_volume                     991.6(4)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      173.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.940
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14786
_diffrn_reflns_theta_full        68.29
_diffrn_reflns_theta_max         68.29
_diffrn_reflns_theta_min         4.60
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'light green'
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0462P)²+0.2267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0876
_reflns_number_gt                1632
_reflns_number_total             1713
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo7b01188_si_002.cif
_cod_data_source_block           Win008
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed to
'multi-scan' according to
/home/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.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032558.cif.
;
_cod_database_code               4032558
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.85575(14) 0.81756(17) 0.43852(6) 0.0337(3) Uani d . . 1
H H1A 0.8131 0.9156 0.4712 0.051 Uiso calc U R 1
H H1B 0.8442 0.8786 0.3918 0.051 Uiso calc U R 1
H H1C 0.9742 0.7884 0.4532 0.051 Uiso calc U R 1
C C2 0.71846(15) 0.52305(19) 0.37129(5) 0.0370(3) Uani d . . 1
H H2A 0.7862 0.3966 0.3693 0.056 Uiso calc U R 1
H H2B 0.7411 0.6173 0.3336 0.056 Uiso calc U R 1
H H2C 0.5994 0.4858 0.3661 0.056 Uiso calc U R 1
C C3 0.74850(11) 0.51863(15) 0.49816(5) 0.0244(2) Uani d . . 1
C C4 0.81372(13) 0.59998(16) 0.56321(5) 0.0276(2) Uani d . . 1
H H4 0.8677 0.7319 0.5654 0.033 Uiso calc U R 1
C C5 0.80031(12) 0.49059(15) 0.62385(5) 0.0270(2) Uani d . . 1
H H5 0.8447 0.549 0.6671 0.032 Uiso calc U R 1
C C6 0.72337(11) 0.29720(15) 0.62278(5) 0.0238(2) Uani d . . 1
C C7 0.65650(12) 0.21579(16) 0.55914(5) 0.0265(2) Uani d . . 1
H H7 0.6019 0.0843 0.5576 0.032 Uiso calc U R 1
C C8 0.66830(12) 0.32343(16) 0.49802(5) 0.0274(2) Uani d . . 1
H H8 0.6215 0.2648 0.4551 0.033 Uiso calc U R 1
C C9 0.72368(12) 0.17492(16) 0.69038(5) 0.0256(2) Uani d . . 1
H H9 0.7336 0.2767 0.7298 0.031 Uiso calc U R 1
C C10 0.86907(13) 0.03193(15) 0.70048(5) 0.0262(2) Uani d . . 1
C C11 0.56899(13) 0.05343(17) 0.69376(5) 0.0323(3) Uani d . . 1
N N1 0.76101(11) 0.62578(14) 0.43764(4) 0.0309(2) Uani d . . 1
N N2 0.44898(13) -0.03963(18) 0.69612(6) 0.0488(3) Uani d . . 1
N N3 0.98280(12) -0.07520(15) 0.70701(5) 0.0357(2) Uani d . . 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 H2A 109.5
N1 C2 H2B 109.5
H2A C2 H2B 109.5
N1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
N1 C3 C8 121.42(9)
N1 C3 C4 121.43(10)
C8 C3 C4 117.15(9)
C5 C4 C3 120.91(10)
C5 C4 H4 119.5
C3 C4 H4 119.5
C4 C5 C6 121.28(9)
C4 C5 H5 119.4
C6 C5 H5 119.4
C5 C6 C7 118.57(9)
C5 C6 C9 119.33(9)
C7 C6 C9 121.99(9)
C8 C7 C6 120.90(9)
C8 C7 H7 119.5
C6 C7 H7 119.5
C7 C8 C3 121.18(9)
C7 C8 H8 119.4
C3 C8 H8 119.4
C11 C9 C10 108.79(9)
C11 C9 C6 112.87(8)
C10 C9 C6 111.02(8)
C11 C9 H9 108.0
C10 C9 H9 108.0
C6 C9 H9 108.0
N3 C10 C9 178.25(11)
N2 C11 C9 179.61(13)
C3 N1 C1 120.34(9)
C3 N1 C2 119.69(9)
C1 N1 C2 118.03(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.4466(15)
C1 H1A 0.98
C1 H1B 0.98
C1 H1C 0.98
C2 N1 1.4500(14)
C2 H2A 0.98
C2 H2B 0.98
C2 H2C 0.98
C3 N1 1.3712(13)
C3 C8 1.4090(15)
C3 C4 1.4090(15)
C4 C5 1.3816(15)
C4 H4 0.95
C5 C6 1.3861(15)
C5 H5 0.95
C6 C7 1.3897(14)
C6 C9 1.5251(14)
C7 C8 1.3818(14)
C7 H7 0.95
C8 H8 0.95
C9 C11 1.4746(15)
C9 C10 1.4814(14)
C9 H9 1.0
C10 N3 1.1394(14)
C11 N2 1.1392(15)
