#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:04:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180464 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/33/7213372.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_7213372
loop_
_publ_author_name
'Tandel, Sagun'
'Wang, Anlai'
'Zhang, Hongming'
'Yousuf, Pervaiz'
'Biehl, Edward R.'
_publ_section_title
;
 Investigation of the reaction of 2-bromo-1-naphthol with
 arylacetonitriles and LiTMP: facile synthesis of
 3-arylmethyl-1-hydroxynaphthalene-2-carbonitriles
;
_journal_issue                   18
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              3149
_journal_paper_doi               10.1039/b003935g
_journal_year                    2000
_chemical_formula_sum            'C16 H11 N O S'
_chemical_formula_weight         265.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.131(1)
_cell_length_b                   12.598(2)
_cell_length_c                   13.699(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    228(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     1230.7(3)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      228(2)
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            903
_diffrn_reflns_theta_max         22.00
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        1.50
_diffrn_standards_interval_count 147
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   n/a
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       plates
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(19)
_refine_ls_extinction_coef       0.0010(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.040
_refine_ls_goodness_of_fit_obs   1.048
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_restrained_S_obs      1.048
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_obs          0.0322
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0395P)²+0.2499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0897
_refine_ls_wR_factor_obs         0.0769
_reflns_number_observed          787
_reflns_number_total             903
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b003935gsup1.cif
_cod_data_source_block           st-587
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+0.2499P] 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^)+(0.0395P)^2^+0.2499P] 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      P2(1)2(1)2(1)
_cod_database_code               7213372
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
_atom_site_refinement_flags
N1 N -0.2822(5) 0.6864(3) 0.5416(3) 0.0491(11) Uani 1 d .
H1A H -0.1878(5) 0.7089(3) 0.5084(3) 0.059 Uiso 1 calc R
H1B H -0.3693(5) 0.7297(3) 0.5587(3) 0.059 Uiso 1 calc R
O2 O -0.6053(4) 0.7055(2) 0.6327(2) 0.0468(9) Uani 1 d .
S1 S 0.0447(2) 0.54364(9) 0.47035(9) 0.0433(4) Uani 1 d .
C2 C -0.2935(6) 0.5821(3) 0.5671(3) 0.0310(11) Uani 1 d .
C3 C -0.5984(6) 0.6087(3) 0.6538(3) 0.0340(12) Uani 1 d .
C4 C -0.9030(6) 0.6288(4) 0.7395(3) 0.0444(13) Uani 1 d .
H4 H -0.9022(6) 0.6998(4) 0.7209(3) 0.053 Uiso 1 calc R
C5 C -1.0511(9) 0.5908(4) 0.7934(4) 0.0507(13) Uani 1 d .
H5 H -1.1507(9) 0.6349(4) 0.8100(4) 0.061 Uiso 1 calc R
C6 C -1.0491(8) 0.4853(4) 0.8228(3) 0.0542(15) Uani 1 d .
H6 H -1.1478(8) 0.4586(4) 0.8598(3) 0.065 Uiso 1 calc R
C7 C -0.9023(7) 0.4200(4) 0.7976(3) 0.0461(13) Uani 1 d .
H7 H -0.9011(7) 0.3499(4) 0.8188(3) 0.055 Uiso 1 calc R
C8 C -0.5992(6) 0.3846(3) 0.7101(3) 0.0398(12) Uani 1 d .
H8A H -0.5442(6) 0.3545(3) 0.7686(3) 0.048 Uiso 1 calc R
H8B H -0.6540(6) 0.3265(3) 0.6734(3) 0.048 Uiso 1 calc R
C9 C -0.3019(6) 0.3654(3) 0.6209(3) 0.0357(11) Uani 1 d .
H9 H -0.3044(6) 0.2942(3) 0.6387(3) 0.043 Uiso 1 calc R
C10 C 0.0069(6) 0.3505(4) 0.5260(3) 0.0454(12) Uani 1 d .
H10 H 0.0301(6) 0.2785(4) 0.5353(3) 0.054 Uiso 1 calc R
C11 C 0.1212(7) 0.4146(4) 0.4746(4) 0.0488(12) Uani 1 d .
H11 H 0.2306(7) 0.3913(4) 0.4445(4) 0.059 Uiso 1 calc R
C12 C -0.1525(6) 0.5118(3) 0.5395(3) 0.0313(10) Uani 1 d .
C13 C -0.1534(6) 0.4038(3) 0.5648(3) 0.0322(11) Uani 1 d .
C14 C -0.4448(6) 0.4316(3) 0.6501(3) 0.0306(10) Uani 1 d .
C15 C -0.4446(6) 0.5415(3) 0.6239(3) 0.0302(9) Uani 1 d .
C16 C -0.7546(6) 0.5641(3) 0.7119(3) 0.0325(11) Uani 1 d .
C17 C -0.7548(5) 0.4583(4) 0.7404(3) 0.0352(11) Uani 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'
S S 0.1246 0.1234 '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
C11 S1 C12 91.2(2)
N1 C2 C12 120.0(4)
N1 C2 C15 122.1(4)
C12 C2 C15 117.9(3)
O2 C3 C15 122.3(4)
O2 C3 C16 117.6(4)
C15 C3 C16 120.1(4)
C5 C4 C16 121.8(5)
C4 C5 C6 118.7(6)
C7 C6 C5 120.5(5)
C6 C7 C17 120.5(5)
C14 C8 C17 116.7(4)
C14 C9 C13 120.8(4)
C11 C10 C13 113.4(4)
C10 C11 S1 113.2(3)
C2 C12 C13 123.1(4)
C2 C12 S1 125.8(3)
C13 C12 S1 111.1(3)
C9 C13 C12 118.4(4)
C9 C13 C10 130.5(4)
C12 C13 C10 111.1(4)
C9 C14 C15 120.8(4)
C9 C14 C8 117.7(4)
C15 C14 C8 121.5(4)
C2 C15 C14 119.0(4)
C2 C15 C3 121.3(3)
C14 C15 C3 119.7(4)
C4 C16 C17 119.1(4)
C4 C16 C3 119.8(4)
C17 C16 C3 121.1(4)
C16 C17 C7 119.3(4)
C16 C17 C8 120.9(4)
C7 C17 C8 119.8(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.362(5)
O2 C3 1.254(5)
S1 C11 1.716(5)
S1 C12 1.742(4)
C2 C12 1.392(6)
C2 C15 1.424(6)
C3 C15 1.444(6)
C3 C16 1.481(6)
C4 C5 1.375(6)
C4 C16 1.387(6)
C5 C6 1.388(7)
C6 C7 1.375(7)
C7 C17 1.397(6)
C8 C14 1.496(6)
C8 C17 1.506(6)
C9 C14 1.376(6)
C9 C13 1.395(6)
C10 C11 1.346(6)
C10 C13 1.429(6)
C12 C13 1.404(5)
C14 C15 1.431(6)
C16 C17 1.389(5)
