#------------------------------------------------------------------------------
#$Date: 2016-08-04 08:50:48 +0300 (Thu, 04 Aug 2016) $
#$Revision: 184814 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/61/7226110.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_7226110
loop_
_publ_author_name
'Panja, Sumit Kumar'
'Dwivedi, Nidhi'
'Saha, Satyen'
_publ_section_title
;
 Manipulating the proton transfer process in molecular complexes:
 synthesis and spectroscopic studies.
;
_journal_issue                   31
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              21600
_journal_page_last               21609
_journal_paper_doi               10.1039/c6cp03797f
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         C14H8N2
_chemical_formula_sum            'C14 H8 N2'
_chemical_formula_weight         204.22
_chemical_melting_point          439.5
_chemical_name_common            2-(naphthalen-1-ylmethylene)malononitrile
_chemical_name_systematic        2-(naphthalen-1-ylmethylene)malononitrile
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/cc10gy1g
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-07-16 deposited with the CCDC.
2016-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.000
_cell_angle_beta                 91.290
_cell_angle_gamma                90.000
_cell_formula_units_Z            4
_cell_length_a                   3.8269(4)
_cell_length_b                   15.7916(15)
_cell_length_c                   17.2303(16)
_cell_measurement_reflns_used    940
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      1.0000
_cell_measurement_theta_min      0.96559
_cell_volume                     1041.01(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4249
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.002
_diffrn_reflns_theta_min         3.501
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      1.32
_exptl_crystal_description       rectangualr
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0486P)²+0.0749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1558
_reflns_number_total             2767
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cp03797f2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '439.5K' was changed to '439.5' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_cell_volume        1041.02(17)
_cod_database_code               7226110
_shelx_shelxl_version_number     2014/7
_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.
;
_exptl_absorpt_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) 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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C9 C 0.4938(3) 0.08696(9) 0.23109(9) 0.0354(4) Uani 1 1 d . .
C1 C 0.3709(4) 0.13975(9) 0.29248(8) 0.0358(4) Uani 1 1 d . .
N16 N 0.6779(4) 0.28231(10) 0.45655(9) 0.0667(5) Uani 1 1 d . .
C8 C 0.5678(4) -0.00005(10) 0.24022(10) 0.0439(4) Uani 1 1 d . .
H8 H 0.5375 -0.0257 0.2882 0.053 Uiso 1 1 calc R U
C11 C 0.2984(4) 0.10329(10) 0.36780(9) 0.0407(4) Uani 1 1 d . .
C4 C 0.4886(4) 0.21186(10) 0.14740(10) 0.0490(4) Uani 1 1 d . .
H4 H 0.5290 0.2366 0.0994 0.059 Uiso 1 1 calc R U
C3 C 0.3681(4) 0.26050(10) 0.20609(10) 0.0496(4) Uani 1 1 d . .
H3 H 0.3251 0.3178 0.1980 0.059 Uiso 1 1 calc R U
C6 C 0.7369(4) -0.00998(11) 0.10683(11) 0.0551(5) Uani 1 1 d . .
H6 H 0.8142 -0.0428 0.0658 0.066 Uiso 1 1 calc R U
C13 C 0.2532(5) 0.10119(10) 0.50847(10) 0.0491(4) Uani 1 1 d . .
C2 C 0.3086(4) 0.22435(9) 0.27873(9) 0.0427(4) Uani 1 1 d . .
H2 H 0.2253 0.2581 0.3185 0.051 Uiso 1 1 calc R U
C14 C 0.5301(4) 0.22057(10) 0.44665(9) 0.0454(4) Uani 1 1 d . .
C12 C 0.3549(4) 0.14064(9) 0.43726(9) 0.0406(4) Uani 1 1 d . .
N15 N 0.1708(5) 0.07159(10) 0.56556(9) 0.0710(5) Uani 1 1 d . .
C10 C 0.5536(4) 0.12459(10) 0.15771(9) 0.0399(4) Uani 1 1 d . .
C5 C 0.6762(4) 0.07381(11) 0.09640(10) 0.0520(5) Uani 1 1 d . .
H5 H 0.7155 0.0983 0.0483 0.062 Uiso 1 1 calc R U
C7 C 0.6833(4) -0.04709(11) 0.17938(11) 0.0521(5) Uani 1 1 d . .
H7 H 0.7270 -0.1046 0.1863 0.062 Uiso 1 1 calc R U
H1 H 0.207(4) 0.0453(10) 0.3689(9) 0.045(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_
_citation_id
_citation_doi
_citation_year
1 10.1039/C5RA09036A 2015
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 C9 C10 118.07(14)
C8 C9 C1 123.50(14)
C10 C9 C1 118.40(14)
C2 C1 C9 119.70(14)
C2 C1 C11 120.17(14)
C9 C1 C11 120.07(13)
C7 C8 C9 120.75(16)
C7 C8 H8 119.6
C9 C8 H8 119.6
C12 C11 C1 126.16(14)
C12 C11 H1 116.2(9)
C1 C11 H1 117.6(9)
C3 C4 C10 121.35(15)
C3 C4 H4 119.3
C10 C4 H4 119.3
C4 C3 C2 120.01(15)
C4 C3 H3 120.0
C2 C3 H3 120.0
C5 C6 C7 119.94(16)
C5 C6 H6 120.0
C7 C6 H6 120.0
N15 C13 C12 178.51(18)
C1 C2 C3 121.25(15)
C1 C2 H2 119.4
C3 C2 H2 119.4
N16 C14 C12 177.01(18)
C11 C12 C14 123.35(14)
C11 C12 C13 121.82(14)
C14 C12 C13 114.79(14)
C4 C10 C5 121.33(15)
C4 C10 C9 119.29(14)
C5 C10 C9 119.38(15)
C6 C5 C10 120.89(16)
C6 C5 H5 119.6
C10 C5 H5 119.6
C8 C7 C6 120.94(16)
C8 C7 H7 119.5
C6 C7 H7 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C9 C8 1.411(2)
C9 C10 1.420(2)
C9 C1 1.434(2)
C1 C2 1.377(2)
C1 C11 1.452(2)
N16 C14 1.138(2)
C8 C7 1.366(2)
C8 H8 0.9300
C11 C12 1.347(2)
C11 H1 0.981(15)
C4 C3 1.359(2)
C4 C10 1.411(2)
C4 H4 0.9300
C3 C2 1.399(2)
C3 H3 0.9300
C6 C5 1.355(2)
C6 C7 1.400(2)
C6 H6 0.9300
C13 N15 1.140(2)
C13 C12 1.438(2)
C2 H2 0.9300
C14 C12 1.437(2)
C10 C5 1.415(2)
C5 H5 0.9300
C7 H7 0.9300
