#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/24/8102478.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_8102478
loop_
_publ_author_name
'Chun-Yang Zheng'
'Ting-Quan Sun'
_publ_section_title
;
 Crystal structure of 3-(furan-2-yl)-5-(naphthalen-6-yl)-1H-pyrazole,
 C17H12N2O
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              457
_journal_volume                  224
_journal_year                    2009
_chemical_formula_moiety         'C17 H12 N2 O'
_chemical_formula_sum            'C17 H12 N2 O'
_chemical_formula_weight         260.29
_chemical_name_systematic
; 
3-(furan-2-yl)-5-(naphthalen-6-yl)-1H-pyrazole, 
C₁₇H₁₂N₂O
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.271(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4840(17)
_cell_length_b                   5.8533(7)
_cell_length_c                   15.3242(17)
_cell_measurement_reflns_used    2164
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.75
_cell_measurement_theta_min      2.68
_cell_volume                     1288.7(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0903
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9469
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_correction_T_min  0.9831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, (Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0646
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0605P)²+0.2261P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1509
_refine_ls_wR_factor_ref         0.1640
_reflns_number_gt                2100
_reflns_number_total             2799
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2662.cff
_cod_data_source_block           am
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               8102478
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.79503(13) 0.8619(4) 0.53872(13) 0.0453(5) Uani 1 4 e d . . .
C2 C 0.84375(15) 0.8341(4) 0.46480(14) 0.0570(6) Uani 1 4 e d . . .
H2 H 0.8931 0.9312 0.4579 0.068 Uiso 1 4 e calc R . .
C3 C 0.81994(16) 0.6691(4) 0.40399(14) 0.0604(6) Uani 1 4 e d . . .
H3 H 0.8525 0.6572 0.3556 0.072 Uiso 1 4 e calc R . .
C4 C 0.74690(14) 0.5154(4) 0.41258(13) 0.0512(5) Uani 1 4 e d . . .
C5 C 0.72103(17) 0.3377(4) 0.35173(16) 0.0649(7) Uani 1 4 e d . . .
H5 H 0.7524 0.3220 0.3027 0.078 Uiso 1 4 e calc R . .
C6 C 0.65198(19) 0.1905(4) 0.36328(18) 0.0727(7) Uani 1 4 e d . . .
H6 H 0.6364 0.0744 0.3226 0.087 Uiso 1 4 e calc R . .
C7 C 0.60371(19) 0.2125(5) 0.43649(18) 0.0755(8) Uani 1 4 e d . . .
H7 H 0.5564 0.1100 0.4444 0.091 Uiso 1 4 e calc R . .
C8 C 0.62566(17) 0.3835(4) 0.49644(16) 0.0676(7) Uani 1 4 e d . . .
H8 H 0.5926 0.3975 0.5444 0.081 Uiso 1 4 e calc R . .
C9 C 0.69766(14) 0.5383(4) 0.48613(13) 0.0507(5) Uani 1 4 e d . . .
C10 C 0.72365(14) 0.7149(4) 0.54791(13) 0.0506(5) Uani 1 4 e d . . .
H10 H 0.6911 0.7310 0.5961 0.061 Uiso 1 4 e calc R . .
C11 C 0.82323(13) 1.0448(3) 0.60146(12) 0.0444(5) Uani 1 4 e d . . .
C12 C 0.88473(13) 1.2222(4) 0.59870(13) 0.0479(5) Uani 1 4 e d . . .
H12 H 0.9200 1.2552 0.5536 0.057 Uiso 1 4 e calc R . .
C13 C 0.88383(13) 1.3425(3) 0.67667(13) 0.0440(5) Uani 1 4 e d . A .
C14 C 0.93773(15) 1.5393(4) 0.70716(15) 0.0525(6) Uani 1 4 e d D . .
C15 C 0.9403(11) 1.631(3) 0.7887(8) 0.069(5) Uani 0.53 4 e d PD A 1
H15 H 0.9091 1.5815 0.8347 0.083 Uiso 0.53 4 e calc PR A 1
O1 O 0.9984(6) 1.6441(14) 0.6637(5) 0.069(4) Uani 0.53 4 e d PD A 1
C15' C 0.9951(11) 1.646(2) 0.6571(9) 0.065(6) Uani 0.47 4 e d PD A 2
H15' H 1.0051 1.6119 0.5998 0.078 Uiso 0.47 4 e calc PR A 2
O1' O 0.9396(8) 1.648(2) 0.7821(6) 0.069(4) Uani 0.47 4 e d PD A 2
C16 C 1.03715(17) 1.8235(4) 0.71307(19) 0.0684(7) Uani 1 4 e d D . .
H16 H 1.0802 1.9276 0.6964 0.082 Uiso 1 4 e calc R A 1
C17 C 1.00264(18) 1.8216(5) 0.78741(19) 0.0709(7) Uani 1 4 e d D A .
H17 H 1.0161 1.9271 0.8326 0.085 Uiso 1 4 e calc R B 1
H1A H 0.7521(18) 0.967(5) 0.7010(17) 0.085 Uiso 1 4 e d . . .
N1 N 0.78938(13) 1.0667(3) 0.67876(11) 0.0513(5) Uani 1 4 e d . A .
N2 N 0.82542(13) 1.2467(3) 0.72652(11) 0.0532(5) Uani 1 4 e 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C1 C2 118.0(2) . . ?
C10 C1 C11 123.06(18) . . ?
C2 C1 C11 118.91(19) . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C9 118.4(2) . . ?
C3 C4 C5 123.2(2) . . ?
C9 C4 C5 118.4(2) . . ?
C6 C5 C4 121.5(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 120.6(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 119.0(2) . . ?
C8 C9 C10 122.2(2) . . ?
C4 C9 C10 118.8(2) . . ?
C1 C10 C9 122.01(19) . . ?
C1 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
N1 C11 C12 105.41(18) . . ?
N1 C11 C1 123.13(18) . . ?
C12 C11 C1 131.47(18) . . ?
C11 C12 C13 106.29(17) . . ?
C11 C12 H12 126.9 . . ?
C13 C12 H12 126.9 . . ?
N2 C13 C12 110.82(18) . . ?
N2 C13 C14 120.62(19) . . ?
C12 C13 C14 128.53(19) . . ?
O1' C14 O1 106.0(5) . . ?
O1' C14 C15' 109.1(7) . . ?
O1 C14 C15' 4.3(11) . . ?
O1' C14 C15 5.8(14) . . ?
O1 C14 C15 109.8(6) . . ?
C15' C14 C15 113.1(8) . . ?
O1' C14 C13 128.6(4) . . ?
O1 C14 C13 125.3(4) . . ?
C15' C14 C13 122.2(6) . . ?
C15 C14 C13 124.6(5) . . ?
C14 C15 C17 103.8(8) . . ?
C14 C15 H15 128.1 . . ?
C17 C15 H15 128.1 . . ?
C14 O1 C16 109.2(5) . . ?
C14 C15' C16 103.9(8) . . ?
C14 C15' H15' 128.1 . . ?
C16 C15' H15' 128.1 . . ?
C14 O1' C17 110.7(5) . . ?
C17 C16 O1 107.5(3) . . ?
C17 C16 C15' 109.7(4) . . ?
O1 C16 C15' 3.6(10) . . ?
C17 C16 H16 126.2 . . ?
O1 C16 H16 126.2 . . ?
C15' C16 H16 124.0 . . ?
C16 C17 O1' 106.5(3) . . ?
C16 C17 C15 109.3(4) . . ?
O1' C17 C15 4.9(13) . . ?
C16 C17 H17 125.4 . . ?
O1' C17 H17 128.0 . . ?
C15 C17 H17 125.4 . . ?
C11 N1 N2 113.14(17) . . ?
C11 N1 H1A 125.4(17) . . ?
N2 N1 H1A 121.1(17) . . ?
C13 N2 N1 104.34(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C10 1.366(3) . ?
C1 C2 1.418(3) . ?
C1 C11 1.462(3) . ?
C2 C3 1.356(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.407(3) . ?
C3 H3 0.9300 . ?
C4 C9 1.414(3) . ?
C4 C5 1.416(3) . ?
C5 C6 1.348(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.369(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.405(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.420(3) . ?
C10 H10 0.9300 . ?
C11 N1 1.344(2) . ?
C11 C12 1.372(3) . ?
C12 C13 1.388(3) . ?
C12 H12 0.9300 . ?
C13 N2 1.333(3) . ?
C13 C14 1.436(3) . ?
C14 O1' 1.310(6) . ?
C14 O1 1.320(6) . ?
C14 C15' 1.353(8) . ?
C14 C15 1.355(8) . ?
C15 C17 1.438(11) . ?
C15 H15 0.9300 . ?
O1 C16 1.372(7) . ?
C15' C16 1.433(13) . ?
C15' H15' 0.9300 . ?
O1' C17 1.362(8) . ?
C16 C17 1.301(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
N1 N2 1.350(2) . ?
N1 H1A 0.89(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A N2 0.89(3) 2.11(3) 2.999(2) 171(2) 2_646
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 0.9(3) . . . . ?
C11 C1 C2 C3 -179.25(19) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 C9 0.7(3) . . . . ?
C2 C3 C4 C5 -178.6(2) . . . . ?
C3 C4 C5 C6 178.5(2) . . . . ?
C9 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
C7 C8 C9 C4 0.3(3) . . . . ?
C7 C8 C9 C10 -178.7(2) . . . . ?
C3 C4 C9 C8 -178.9(2) . . . . ?
C5 C4 C9 C8 0.4(3) . . . . ?
C3 C4 C9 C10 0.2(3) . . . . ?
C5 C4 C9 C10 179.46(19) . . . . ?
C2 C1 C10 C9 -0.1(3) . . . . ?
C11 C1 C10 C9 -179.90(17) . . . . ?
C8 C9 C10 C1 178.5(2) . . . . ?
C4 C9 C10 C1 -0.5(3) . . . . ?
C10 C1 C11 N1 8.5(3) . . . . ?
C2 C1 C11 N1 -171.35(19) . . . . ?
C10 C1 C11 C12 -171.6(2) . . . . ?
C2 C1 C11 C12 8.5(3) . . . . ?
N1 C11 C12 C13 0.0(2) . . . . ?
C1 C11 C12 C13 -179.88(19) . . . . ?
C11 C12 C13 N2 0.3(2) . . . . ?
C11 C12 C13 C14 178.20(19) . . . . ?
N2 C13 C14 O1' 0.6(10) . . . . ?
C12 C13 C14 O1' -177.2(9) . . . . ?
N2 C13 C14 O1 178.8(6) . . . . ?
C12 C13 C14 O1 1.1(7) . . . . ?
N2 C13 C14 C15' -177.6(10) . . . . ?
C12 C13 C14 C15' 4.7(10) . . . . ?
N2 C13 C14 C15 5.7(12) . . . . ?
C12 C13 C14 C15 -172.1(11) . . . . ?
O1' C14 C15 C17 -44(10) . . . . ?
O1 C14 C15 C17 6.1(16) . . . . ?
C15' C14 C15 C17 3.1(18) . . . . ?
C13 C14 C15 C17 -179.9(5) . . . . ?
O1' C14 O1 C16 -0.9(11) . . . . ?
C15' C14 O1 C16 135(14) . . . . ?
C15 C14 O1 C16 -5.5(13) . . . . ?
C13 C14 O1 C16 -179.5(4) . . . . ?
O1' C14 C15' C16 3.9(15) . . . . ?
O1 C14 C15' C16 -41(13) . . . . ?
C15 C14 C15' C16 -0.6(17) . . . . ?
C13 C14 C15' C16 -177.7(5) . . . . ?
O1 C14 O1' C17 -0.8(13) . . . . ?
C15' C14 O1' C17 -4.0(15) . . . . ?
C15 C14 O1' C17 131(12) . . . . ?
C13 C14 O1' C17 177.7(5) . . . . ?
C14 O1 C16 C17 2.4(8) . . . . ?
C14 O1 C16 C15' -126(14) . . . . ?
C14 C15' C16 C17 -2.5(13) . . . . ?
C14 C15' C16 O1 50(13) . . . . ?
O1 C16 C17 O1' -2.8(9) . . . . ?
C15' C16 C17 O1' 0.2(11) . . . . ?
O1 C16 C17 C15 1.5(11) . . . . ?
C15' C16 C17 C15 4.4(13) . . . . ?
C14 O1' C17 C16 2.3(12) . . . . ?
C14 O1' C17 C15 -123(12) . . . . ?
C14 C15 C17 C16 -4.6(15) . . . . ?
C14 C15 C17 O1' 51(10) . . . . ?
C12 C11 N1 N2 -0.3(2) . . . . ?
C1 C11 N1 N2 179.61(17) . . . . ?
C12 C13 N2 N1 -0.4(2) . . . . ?
C14 C13 N2 N1 -178.54(17) . . . . ?
C11 N1 N2 C13 0.5(2) . . . . ?
