#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/42/7204261.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_7204261
loop_
_publ_author_name
'Kyu-Tae Chang'
'Yong Hyun Choi'
'Seung-Ho Kim'
'Yong-Jin Yoon'
'Woo Song Lee'
_publ_section_title
;
 Regioselective synthesis of pyrazoles via the ring cleavage of
 3-substituted N-alkylated 3-hydroxyisoindolin-1-ones
;
_journal_issue                   2
_journal_name_full               'J. Chem. Soc., Perkin Trans. 1'
_journal_page_first              207
_journal_page_last               210
_journal_paper_doi               10.1039/b108485m
_journal_year                    2002
_chemical_formula_sum            'C14 H17 N3 O'
_chemical_formula_weight         243.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 113.20(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.922(2)
_cell_length_b                   9.557(1)
_cell_length_c                   13.551(3)
_cell_measurement_reflns_used    4520
_cell_measurement_temperature    123.2
_cell_measurement_theta_max      27.25
_cell_measurement_theta_min      2.7
_cell_volume                     1300.1(4)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'teXsan (MSC & Rigaku, 1999)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'teXsan (MSC & Rigaku, 1999)'
_computing_structure_refinement  'teXsan (MSC & Rigaku, 1999)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9135
_diffrn_reflns_theta_full        27.25
_diffrn_reflns_theta_max         27.25
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.47
_refine_ls_extinction_coef       0.020(5)
_refine_ls_extinction_method     'Zachariasen(1967) type 2 Gaussian isotropic'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2890
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.08400(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1538
_reflns_number_gt                2052
_reflns_number_total             2890
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            b108485m.txt
_cod_data_source_block           RGK485raplt_Gyeongsang_Nat
_cod_depositor_comments
;
The following automatic conversions were performed:
data name '_geom_hbond_site_distance_dh' replaced with
'_geom_hbond_distance_DH' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_hbond_site_distance_ha' replaced with
'_geom_hbond_distance_HA' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_hbond_site_distance_da' replaced with
'_geom_hbond_distance_DA' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 5005 2017-03-03 11:38:54Z antanas 
;
_cod_original_cell_volume        1300.0(4)
_cod_original_formula_sum        'C14 H17 N3 O '
_cod_database_code               7204261
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
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_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7166(1) 0.2059(2) 0.1720(1) 0.0188(3) Uani 1.00 d . . .
N1 N 0.4639(2) 0.5955(2) 0.2507(1) 0.0183(4) Uani 1.00 d . . .
N2 N 0.3945(2) 0.5136(2) 0.1662(1) 0.0176(4) Uani 1.00 d . . .
N3 N 0.7426(1) 0.2814(2) 0.0225(1) 0.0155(4) Uani 1.00 d . . .
C1 C 0.4395(2) 0.3466(2) 0.0514(1) 0.0142(4) Uani 1.00 d . . .
C2 C 0.5215(2) 0.2625(2) 0.0174(1) 0.0142(4) Uani 1.00 d . . .
C3 C 0.4656(2) 0.1749(2) -0.0714(2) 0.0190(5) Uani 1.00 d . . .
C4 C 0.3286(2) 0.1658(2) -0.1266(2) 0.0234(5) Uani 1.00 d . . .
C5 C 0.2468(2) 0.2465(2) -0.0935(2) 0.0214(5) Uani 1.00 d . . .
C6 C 0.3013(2) 0.3357(2) -0.0072(2) 0.0180(5) Uani 1.00 d . . .
C7 C 0.4873(2) 0.4445(2) 0.1431(1) 0.0153(4) Uani 1.00 d . . .
C8 C 0.6158(2) 0.4842(2) 0.2146(2) 0.0210(5) Uani 1.00 d . . .
C9 C 0.5958(2) 0.5804(2) 0.2816(2) 0.0230(5) Uani 1.00 d . . .
C10 C 0.6695(2) 0.2501(2) 0.0786(1) 0.0143(4) Uani 1.00 d . . .
C11 C 0.8889(2) 0.2641(2) 0.0599(2) 0.0205(5) Uani 1.00 d . . .
C12 C 0.9600(2) 0.3642(3) 0.1525(2) 0.0289(6) Uani 1.00 d . . .
C13 C 0.9272(2) 0.1127(3) 0.0936(2) 0.0341(7) Uani 1.00 d . . .
C14 C 0.9223(2) 0.3000(3) -0.0360(2) 0.0319(6) Uani 1.00 d . . .
H1N H 0.4239 0.6570 0.2845 0.0220 Uiso 1.00 calc . . .
H3 H 0.5222 0.1205 -0.0945 0.0227 Uiso 1.00 calc . . .
H3N H 0.6968 0.3181 -0.0476 0.0185 Uiso 1.00 calc . . .
H4 H 0.2915 0.1048 -0.1864 0.0281 Uiso 1.00 calc . . .
H5 H 0.1528 0.2406 -0.1303 0.0257 Uiso 1.00 calc . . .
H6 H 0.2435 0.3917 0.0134 0.0216 Uiso 1.00 calc . . .
H8 H 0.6986 0.4512 0.2161 0.0252 Uiso 1.00 calc . . .
H9 H 0.6630 0.6277 0.3393 0.0276 Uiso 1.00 calc . . .
H12a H 1.0536 0.3529 0.1758 0.0347 Uiso 1.00 calc . . .
H12b H 0.9364 0.4578 0.1292 0.0347 Uiso 1.00 calc . . .
H12c H 0.9342 0.3443 0.2103 0.0347 Uiso 1.00 calc . . .
H13a H 1.0189 0.0991 0.1083 0.0410 Uiso 1.00 calc . . .
H13b H 0.9114 0.0928 0.1563 0.0410 Uiso 1.00 calc . . .
H13c H 0.8750 0.0518 0.0373 0.0410 Uiso 1.00 calc . . .
H14a H 0.8816 0.3864 -0.0660 0.0383 Uiso 1.00 calc . . .
H14b H 1.0161 0.3078 -0.0134 0.0383 Uiso 1.00 calc . . .
H14c H 0.8900 0.2282 -0.0885 0.0383 Uiso 1.00 calc . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C9 112.2(2) . . . yes
N2 N1 H1N 123.9 . . . no
C9 N1 H1N 123.9 . . . no
N1 N2 C7 105.1(1) . . . yes
C10 N3 C11 125.9(2) . . . yes
C10 N3 H3N 117.0 . . . no
C11 N3 H3N 117.0 . . . no
C2 C1 C6 116.9(2) . . . yes
C2 C1 C7 125.3(2) . . . yes
C6 C1 C7 117.8(2) . . . yes
C1 C2 C3 120.4(2) . . . yes
C1 C2 C10 123.3(2) . . . yes
C3 C2 C10 116.0(2) . . . yes
C2 C3 C4 121.1(2) . . . yes
C2 C3 H3 119.5 . . . no
C4 C3 H3 119.5 . . . no
C3 C4 C5 119.2(2) . . . yes
C3 C4 H4 120.4 . . . no
C5 C4 H4 120.4 . . . no
C4 C5 C6 120.1(2) . . . yes
C4 C5 H5 119.9 . . . no
C6 C5 H5 119.9 . . . no
C1 C6 C5 122.2(2) . . . yes
C1 C6 H6 118.9 . . . no
C5 C6 H6 118.9 . . . no
N2 C7 C1 117.3(2) . . . yes
N2 C7 C8 110.2(2) . . . yes
C1 C7 C8 132.5(2) . . . yes
C7 C8 C9 105.1(2) . . . yes
C7 C8 H8 127.4 . . . no
C9 C8 H8 127.4 . . . no
N1 C9 C8 107.4(2) . . . yes
N1 C9 H9 126.3 . . . no
C8 C9 H9 126.3 . . . no
O1 C10 N3 123.9(2) . . . yes
O1 C10 C2 121.0(2) . . . yes
N3 C10 C2 115.0(2) . . . yes
N3 C11 C12 109.9(2) . . . yes
N3 C11 C13 109.8(2) . . . yes
N3 C11 C14 105.8(2) . . . yes
C12 C11 C13 111.0(2) . . . yes
C12 C11 C14 110.3(2) . . . yes
C13 C11 C14 109.9(2) . . . yes
C11 C12 H12a 109.5 . . . no
C11 C12 H12b 109.5 . . . no
C11 C12 H12c 109.5 . . . no
H12a C12 H12b 109.5 . . . no
H12a C12 H12c 109.5 . . . no
H12b C12 H12c 109.5 . . . no
C11 C13 H13a 109.5 . . . no
C11 C13 H13b 109.5 . . . no
C11 C13 H13c 109.5 . . . no
H13a C13 H13b 109.5 . . . no
H13a C13 H13c 109.5 . . . no
H13b C13 H13c 109.5 . . . no
C11 C14 H14a 109.5 . . . no
C11 C14 H14b 109.5 . . . no
C11 C14 H14c 109.5 . . . no
H14a C14 H14b 109.5 . . . no
H14a C14 H14c 109.5 . . . no
H14b C14 H14c 109.5 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.238(2) . . yes
N1 N2 1.347(2) . . yes
N1 C9 1.340(3) . . yes
N1 H1N 0.950 . . no
N2 C7 1.345(2) . . yes
N3 C10 1.335(2) . . yes
N3 C11 1.484(2) . . yes
N3 H3N 0.950 . . no
C1 C2 1.408(3) . . yes
C1 C6 1.406(2) . . yes
C1 C7 1.477(3) . . yes
C2 C3 1.394(3) . . yes
C2 C10 1.503(2) . . yes
C3 C4 1.387(3) . . yes
C3 H3 0.950 . . no
C4 C5 1.383(3) . . yes
C4 H4 0.950 . . no
C5 C6 1.378(3) . . yes
C5 H5 0.950 . . no
C6 H6 0.950 . . no
C7 C8 1.408(3) . . yes
C8 C9 1.369(3) . . yes
C8 H8 0.950 . . no
C9 H9 0.950 . . no
C11 C12 1.525(3) . . yes
C11 C13 1.526(3) . . yes
C11 C14 1.520(3) . . yes
C12 H12a 0.950 . . no
C12 H12b 0.950 . . no
C12 H12c 0.950 . . no
C13 H13a 0.950 . . no
C13 H13b 0.950 . . no
C13 H13c 0.950 . . no
C14 H14a 0.950 . . no
C14 H14b 0.950 . . no
C14 H14c 0.950 . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N1 2.780(2) . 2_645 ?
O1 N2 3.429(2) . 2_645 ?
N1 C1 3.440(2) . 2_655 ?
N1 C2 3.472(3) . 2_655 ?
N1 C10 3.509(3) . 2_655 ?
N1 C3 3.530(3) . 4_555 ?
N1 C3 3.575(3) . 3_665 ?
N1 C7 3.588(3) . 2_655 ?
N2 N3 3.099(2) . 3_665 ?
N2 C4 3.596(3) . 4_555 ?
C1 C9 3.526(3) . 2_645 ?
C2 C7 3.523(3) . 3_665 ?
C3 C9 3.539(3) . 3_665 ?
C4 C9 3.513(3) . 3_665 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1N O1 . . 2_655 0.950 1.907 2.779(2) 151.549 no
N3 H3N N2 . . 3_665 0.950 2.214 3.099(2) 154.637 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9229021
