#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:05:58 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180465 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/34/7213442.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7213442
loop_
_publ_author_name
'O’Leary, Jane'
'Bell, Paul C.'
'Wallis, John D.'
'Schweizer, W. Bernd'
_publ_section_title
;
 Attractive and repulsive effects in the interactions between
 electron-rich and electron-deficient groups in peri-substituted
 naphthalenes
;
_journal_issue                   2
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              133
_journal_paper_doi               10.1039/b008226k
_journal_year                    2001
_chemical_formula_sum            'C15 H10 N2 O'
_chemical_formula_weight         234.25
_chemical_name_systematic
; 
  1,1-dicyano-2-(8'-methoxynaphth-1'-yl)ethene 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 99.499(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5046(3)
_cell_length_b                   17.5411(7)
_cell_length_c                   10.3306(3)
_cell_measurement_reflns_used    2612
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.31
_cell_volume                     1162.54(8)
_computing_cell_refinement
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_data_collection
;
DENZO (Otwinowski and Minor, 1997) and  COLLECT (Hooft, 1998)
;
_computing_data_reduction
;
DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998)
;
_computing_molecular_graphics    'ORTEPIII (Johnson and Burnett, 1996)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measurement_device       'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method       'Phi and Omega scans to fill Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9104
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
using multiple and symmetry-related data measurements via the program
SORTAV (Blessing, 1995).
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.058
_refine_ls_goodness_of_fit_obs   1.114
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2441
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_restrained_S_obs      1.114
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_obs          0.0440
_refine_ls_shift/esd_max         0.077
_refine_ls_shift/esd_mean        0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[s²(Fo²)+( 0.0693P)²+0.1014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1248
_refine_ls_wR_factor_obs         0.1135
_reflns_number_observed          2046
_reflns_number_total             2612
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b008226ksup1.cif
_cod_data_source_block           bob
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w=1/[s^2^(Fo^2^)+(
0.0693P)^2^+0.1014P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'.
New tag '_refine_ls_weighting_details' was created. The value of the
new tag was set to 'w=1/[s^2^(Fo^2^)+( 0.0693P)^2^+0.1014P] where
P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7213442
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, 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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
O1 O 0.44390(12) 0.32353(5) 0.19459(8) 0.0320(2) Uani 1 d
N1 N 0.4655(2) 0.43189(7) 0.65951(11) 0.0429(3) Uani 1 d
N2 N -0.1585(2) 0.35642(10) 0.50022(12) 0.0627(4) Uani 1 d
C1 C 0.3048(2) 0.32990(7) 0.08098(11) 0.0280(3) Uani 1 d
C2 C 0.3289(2) 0.29609(8) -0.03532(13) 0.0359(3) Uani 1 d
C3 C 0.1773(2) 0.30627(8) -0.14791(13) 0.0389(3) Uani 1 d
C4 C 0.0034(2) 0.34831(8) -0.14342(12) 0.0350(3) Uani 1 d
C5 C -0.2116(2) 0.42551(8) -0.01894(12) 0.0339(3) Uani 1 d
C6 C -0.2444(2) 0.45907(8) 0.09501(12) 0.0361(3) Uani 1 d
C7 C -0.0944(2) 0.45216(7) 0.20815(12) 0.0317(3) Uani 1 d
C8 C 0.0878(2) 0.41177(7) 0.20880(11) 0.0265(3) Uani 1 d
C9 C 0.1250(2) 0.37526(6) 0.09041(11) 0.0252(3) Uani 1 d
C10 C -0.0281(2) 0.38293(7) -0.02412(11) 0.0287(3) Uani 1 d
C11 C 0.2414(2) 0.41426(7) 0.32958(11) 0.0277(3) Uani 1 d
C12 C 0.1959(2) 0.40458(7) 0.45111(11) 0.0299(3) Uani 1 d
C13 C 0.3486(2) 0.41904(8) 0.56586(12) 0.0327(3) Uani 1 d
C14 C -0.0033(2) 0.37827(8) 0.47666(12) 0.0399(3) Uani 1 d
C15 C 0.6188(2) 0.27369(8) 0.1949(2) 0.0378(3) Uani 1 d
H2 H 0.4517(25) 0.2659(9) -0.0387(16) 0.053(4) Uiso 1 d
H3 H 0.1960(24) 0.2817(10) -0.2278(16) 0.051(4) Uiso 1 d
H4 H -0.1032(22) 0.3563(8) -0.2204(15) 0.039(4) Uiso 1 d
H5 H -0.3175(24) 0.4302(9) -0.0994(16) 0.045(4) Uiso 1 d
H6 H -0.3680(26) 0.4896(9) 0.1040(16) 0.052(4) Uiso 1 d
H7 H -0.1114(22) 0.4796(9) 0.2909(15) 0.044(4) Uiso 1 d
H11 H 0.3825(22) 0.4272(8) 0.3249(13) 0.033(3) Uiso 1 d
H15A H 0.5679(26) 0.2192(10) 0.1720(16) 0.055(4) Uiso 1 d
H15B H 0.7101(25) 0.2939(9) 0.1346(15) 0.046(4) Uiso 1 d
H15C H 0.7008(24) 0.2763(9) 0.2878(17) 0.048(4) Uiso 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'
O O 0.0106 0.0060 '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
C1 O1 C15 117.72(10)
C1 O1 C11 95.06(7)
C15 O1 C11 147.16(8)
O1 C1 C2 124.26(11)
O1 C1 C9 114.88(9)
C2 C1 C9 120.87(11)
C1 C2 C3 120.21(12)
C4 C3 C2 121.01(12)
C3 C4 C10 120.18(12)
C6 C5 C10 120.85(12)
C5 C6 C7 119.79(12)
C8 C7 C6 121.92(11)
C7 C8 C9 119.36(11)
C7 C8 C11 116.97(10)
C9 C8 C11 123.46(10)
C10 C9 C1 117.65(10)
C10 C9 C8 118.23(10)
C1 C9 C8 124.10(10)
C5 C10 C4 120.11(11)
C5 C10 C9 119.83(11)
C4 C10 C9 120.05(11)
C12 C11 C8 124.45(11)
C12 C11 O1 128.95(9)
C8 C11 O1 81.97(7)
C11 C12 C13 121.18(11)
C11 C12 C14 123.64(11)
C13 C12 C14 115.17(10)
N1 C13 C12 177.66(13)
N2 C14 C12 178.01(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3632(14)
O1 C15 1.4345(15)
O1 C11 2.6112(14)
N1 C13 1.150(2)
N2 C14 1.143(2)
C1 C2 1.372(2)
C1 C9 1.431(2)
C2 C3 1.407(2)
C3 C4 1.358(2)
C4 C10 1.419(2)
C5 C6 1.364(2)
C5 C10 1.417(2)
C6 C7 1.399(2)
C7 C8 1.379(2)
C8 C9 1.436(2)
C8 C11 1.465(2)
C9 C10 1.422(2)
C11 C12 1.347(2)
C12 C13 1.438(2)
C12 C14 1.440(2)
