#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/40/7204099.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_7204099
loop_
_publ_author_name
'Kobayashi, Tomoshige'
'Miki, Kiyomi'
'Nikaeen, Behrooz'
'Ohta, Akira'
_publ_section_title
;
 Neighboring group effect of pyridazine and pyrazine rings for
 π-facial selectivity in the reactions of fused
 isopropylidenenorbornene systems with electrophilic reagents
;
_journal_issue                   12
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1372
_journal_paper_doi               10.1039/b101330k
_journal_year                    2001
_chemical_formula_sum            'C20 H17 N5 O2'
_chemical_formula_weight         359.39
_chemical_name_systematic        ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                100.943(3)
_cell_angle_beta                 103.565(3)
_cell_angle_gamma                93.725(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1189(3)
_cell_length_b                   10.5252(4)
_cell_length_c                   11.2494(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      42.54
_cell_measurement_theta_min      21.25
_cell_volume                     911.43(6)
_computing_cell_refinement       'Enraf-Nonius CAD4 Express'
_computing_data_collection       'Enraf-Nonius CAD4 Express'
_computing_data_reduction        teXsan
_computing_structure_refinement  SHELXL-93
_computing_structure_solution    SHELXS-86
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Enraf-Nonius CAD4 diffractometer'
_diffrn_measurement_method       BISECT
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0094
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3977
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         74.30
_diffrn_reflns_theta_min         4.14
_diffrn_standards_interval_count 120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0502(22)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.035
_refine_ls_goodness_of_fit_obs   1.049
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_restrained_S_obs      1.049
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_obs          0.0424
_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)+(0.0647P)²+0.2299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1185
_refine_ls_wR_factor_obs         0.1129
_reflns_number_observed          3307
_reflns_number_total             3704
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            b101330k.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+0.2299P] 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^)+(0.0647P)^2^+0.2299P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        911.43(5)
_cod_database_code               7204099
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_group
C1 C 1.1872(2) 0.6860(2) 1.09527(15) 0.0479(4) Uani 1 d . .
C2 C 1.0663(2) 0.74440(13) 1.14681(12) 0.0371(3) Uani 1 d . .
C3 C 1.0052(2) 0.87879(12) 1.15949(13) 0.0380(3) Uani 1 d . .
C4 C 1.0530(2) 0.93707(15) 1.30000(15) 0.0491(4) Uani 1 d . .
C5 C 0.9623(2) 0.86759(15) 1.35361(14) 0.0484(4) Uani 1 d . .
C6 C 0.8494(2) 0.75861(13) 1.25140(12) 0.0369(3) Uani 1 d . .
C7 C 0.9719(2) 0.67121(12) 1.20291(11) 0.0358(3) Uani 1 d . .
C8 C 1.0037(2) 0.54492(14) 1.20392(14) 0.0448(3) Uani 1 d . .
C9 C 0.8107(2) 0.83705(12) 1.14462(11) 0.0334(3) Uani 1 d . .
C10 C 0.7002(2) 0.94679(13) 1.16369(14) 0.0438(3) Uani 1 d . .
C11 C 0.5731(3) 0.9352(2) 1.2233(2) 0.0663(5) Uani 1 d . .
C12 C 0.7301(3) 1.0591(2) 1.1113(2) 0.0662(5) Uani 1 d . .
C13 C 0.7330(2) 0.77645(12) 0.90909(12) 0.0348(3) Uani 1 d . .
C14 C 0.5117(2) 0.62147(12) 0.88676(12) 0.0340(3) Uani 1 d . .
C15 C 0.5504(2) 0.68942(13) 0.69309(13) 0.0452(3) Uani 1 d . .
C16 C 0.3850(3) 0.6946(2) 0.6299(2) 0.0728(6) Uani 1 d . .
C17 C 0.3494(5) 0.6849(3) 0.5000(2) 0.1027(10) Uani 1 d . .
C18 C 0.4749(5) 0.6676(3) 0.4369(2) 0.1050(11) Uani 1 d . .
C19 C 0.6377(4) 0.6625(3) 0.5020(2) 0.0944(8) Uani 1 d . .
C20 C 0.6781(3) 0.6742(2) 0.6308(2) 0.0666(5) Uani 1 d . .
N1 N 1.1260(2) 0.49283(13) 1.15484(13) 0.0552(4) Uani 1 d . .
N2 N 1.2173(2) 0.56296(15) 1.10105(14) 0.0569(4) Uani 1 d . .
N3 N 0.73649(13) 0.74731(10) 1.02287(9) 0.0317(2) Uani 1 d . .
N4 N 0.58778(13) 0.66353(10) 1.01175(10) 0.0335(3) Uani 1 d . .
N5 N 0.59167(14) 0.69841(10) 0.82532(10) 0.0351(3) Uani 1 d . .
O1 O 0.82911(15) 0.85470(10) 0.88475(10) 0.0517(3) Uani 1 d . .
O2 O 0.39486(12) 0.53414(10) 0.83988(9) 0.0459(3) Uani 1 d . .
H1 H 1.2581(24) 0.7305(18) 1.0523(17) 0.056(5) Uiso 1 d . .
H3 H 1.0336(20) 0.9330(16) 1.1036(15) 0.043(4) Uiso 1 d . .
H4 H 1.1426(27) 1.0128(20) 1.3385(19) 0.070(6) Uiso 1 d . .
H5 H 0.9669(23) 0.8737(18) 1.4418(18) 0.056(5) Uiso 1 d . .
H6 H 0.7500(22) 0.7146(16) 1.2706(15) 0.047(4) Uiso 1 d . .
H8 H 0.9377(22) 0.4886(18) 1.2416(16) 0.051(5) Uiso 1 d . .
H11A H 0.4989(29) 1.0049(23) 1.2276(21) 0.077(6) Uiso 1 d . .
H11B H 0.5504(35) 0.8590(28) 1.2526(25) 0.104(9) Uiso 1 d . .
H12A H 0.6500(32) 1.1222(25) 1.1200(22) 0.087(7) Uiso 1 d . .
H12B H 0.7403(46) 1.0349(36) 1.0227(37) 0.148(13) Uiso 1 d . .
H12C H 0.8444(45) 1.1012(33) 1.1361(32) 0.131(12) Uiso 1 d . .
H16 H 0.2974(28) 0.7024(22) 0.6770(21) 0.072(6) Uiso 1 d . .
H17 H 0.2319(48) 0.6870(36) 0.4689(36) 0.140(12) Uiso 1 d . .
H18 H 0.4480(36) 0.6526(28) 0.3394(29) 0.116(9) Uiso 1 d . .
H19 H 0.7290(44) 0.6495(34) 0.4511(34) 0.137(11) Uiso 1 d . .
H20 H 0.7957(32) 0.6786(24) 0.6823(24) 0.088(7) Uiso 1 d . .
H4N H 0.6035(22) 0.6014(18) 1.0583(17) 0.054(5) 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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 -3 -4
1 -8 6
7 0 -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
N2 C1 C2 121.9(2) . . ?
N2 C1 H1 115.1(11) . . ?
C2 C1 H1 123.0(11) . . ?
C1 C2 C7 117.80(13) . . ?
C1 C2 C3 134.99(14) . . ?
C7 C2 C3 107.20(11) . . ?
C2 C3 C4 105.31(11) . . ?
C2 C3 C9 98.65(10) . . ?
C4 C3 C9 97.67(11) . . ?
C2 C3 H3 116.8(9) . . ?
C4 C3 H3 118.0(10) . . ?
C9 C3 H3 117.1(10) . . ?
C5 C4 C3 108.28(12) . . ?
C5 C4 H4 129.8(12) . . ?
C3 C4 H4 121.9(12) . . ?
C4 C5 C6 107.97(13) . . ?
C4 C5 H5 129.9(11) . . ?
C6 C5 H5 121.9(11) . . ?
C7 C6 C5 105.45(11) . . ?
C7 C6 C9 99.00(10) . . ?
C5 C6 C9 97.75(11) . . ?
C7 C6 H6 116.6(10) . . ?
C5 C6 H6 117.9(10) . . ?
C9 C6 H6 117.0(10) . . ?
C8 C7 C2 118.46(13) . . ?
C8 C7 C6 134.73(13) . . ?
C2 C7 C6 106.82(11) . . ?
N1 C8 C7 121.63(15) . . ?
N1 C8 H8 117.2(10) . . ?
C7 C8 H8 121.2(10) . . ?
N3 C9 C10 110.14(10) . . ?
N3 C9 C6 110.13(10) . . ?
C10 C9 C6 115.91(11) . . ?
N3 C9 C3 110.32(10) . . ?
C10 C9 C3 116.43(11) . . ?
C6 C9 C3 92.82(10) . . ?
C11 C10 C12 122.2(2) . . ?
C11 C10 C9 120.31(14) . . ?
C12 C10 C9 117.45(14) . . ?
C10 C11 H11A 117.7(13) . . ?
C10 C11 H11B 121.3(17) . . ?
H11A C11 H11B 120.7(21) . . ?
C10 C12 H12A 113.8(14) . . ?
C10 C12 H12B 112.9(21) . . ?
H12A C12 H12B 111.6(24) . . ?
C10 C12 H12C 116.0(20) . . ?
H12A C12 H12C 110.6(24) . . ?
H12B C12 H12C 89.5(26) . . ?
O1 C13 N3 127.88(12) . . ?
O1 C13 N5 126.53(12) . . ?
N3 C13 N5 105.58(10) . . ?
O2 C14 N4 126.36(12) . . ?
O2 C14 N5 127.19(12) . . ?
N4 C14 N5 106.44(10) . . ?
C16 C15 C20 121.2(2) . . ?
C16 C15 N5 119.7(2) . . ?
C20 C15 N5 119.14(15) . . ?
C15 C16 C17 118.0(3) . . ?
C15 C16 H16 118.7(13) . . ?
C17 C16 H16 123.3(13) . . ?
C18 C17 C16 121.3(3) . . ?
C18 C17 H17 129.7(23) . . ?
C16 C17 H17 108.9(24) . . ?
C19 C18 C17 119.4(2) . . ?
C19 C18 H18 118.6(16) . . ?
C17 C18 H18 121.9(16) . . ?
C18 C19 C20 120.9(3) . . ?
C18 C19 H19 117.2(20) . . ?
C20 C19 H19 121.9(20) . . ?
C15 C20 C19 119.2(2) . . ?
C15 C20 H20 117.2(14) . . ?
C19 C20 H20 123.4(15) . . ?
N2 N1 C8 120.09(13) . . ?
N1 N2 C1 120.12(13) . . ?
C13 N3 N4 108.83(10) . . ?
C13 N3 C9 124.81(10) . . ?
N4 N3 C9 117.56(9) . . ?
C14 N4 N3 107.41(10) . . ?
C14 N4 H4N 116.8(12) . . ?
N3 N4 H4N 114.7(11) . . ?
C14 N5 C13 110.25(10) . . ?
C14 N5 C15 125.40(11) . . ?
C13 N5 C15 123.94(11) . . ?
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 N2 1.344(2) . ?
C1 C2 1.374(2) . ?
C1 H1 0.98(2) . ?
C2 C7 1.384(2) . ?
C2 C3 1.522(2) . ?
C3 C4 1.529(2) . ?
C3 C9 1.572(2) . ?
C3 H3 0.98(2) . ?
C4 C5 1.322(2) . ?
C4 H4 1.00(2) . ?
C5 C6 1.532(2) . ?
C5 H5 0.97(2) . ?
C6 C7 1.522(2) . ?
C6 C9 1.567(2) . ?
C6 H6 0.99(2) . ?
C7 C8 1.372(2) . ?
C8 N1 1.343(2) . ?
C8 H8 0.99(2) . ?
C9 N3 1.476(2) . ?
C9 C10 1.522(2) . ?
C10 C11 1.367(2) . ?
C10 C12 1.449(2) . ?
C11 H11A 0.98(2) . ?
C11 H11B 0.95(3) . ?
C12 H12A 0.97(3) . ?
C12 H12B 1.00(4) . ?
C12 H12C 0.96(4) . ?
C13 O1 1.210(2) . ?
C13 N3 1.366(2) . ?
C13 N5 1.398(2) . ?
C14 O2 1.221(2) . ?
C14 N4 1.369(2) . ?
C14 N5 1.382(2) . ?
C15 C16 1.374(3) . ?
C15 C20 1.383(3) . ?
C15 N5 1.429(2) . ?
C16 C17 1.404(3) . ?
C16 H16 0.98(2) . ?
C17 C18 1.375(5) . ?
C17 H17 0.94(4) . ?
C18 C19 1.362(5) . ?
C18 H18 1.05(3) . ?
C19 C20 1.388(3) . ?
C19 H19 1.04(3) . ?
C20 H20 0.99(3) . ?
N1 N2 1.330(2) . ?
N3 N4 1.4142(14) . ?
N4 H4N 0.91(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10221904
