 
data_2007jmw0006
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 1-Methyl-1H-indazole-3-carboxylic acid
;
_chemical_name_common             ?
_chemical_melting_point           '213 - 221'
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C9 H8 N2 O2'
_chemical_formula_weight          176.17
 
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'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/n
 
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'
 
_cell_length_a                    7.4546(4)
_cell_length_b                    14.7589(9)
_cell_length_c                    14.8296(7)
_cell_angle_alpha                 90.00
_cell_angle_beta                  94.816(3)
_cell_angle_gamma                 90.00
_cell_volume                      1625.82(15)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3725
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        'cut needle'
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.24
_exptl_crystal_size_mid           0.04
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.439
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              736
_exptl_absorpt_coefficient_mu     0.105
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9753
_exptl_absorpt_correction_T_max   0.9979
_exptl_absorpt_process_details    
'SADABS V2.10 (Sheldrick, G.M., 2003)' 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    '10cm confocal mirrors'
_diffrn_measurement_device_type  
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             14720
_diffrn_reflns_av_R_equivalents   0.0872
_diffrn_reflns_av_sigmaI/netI     0.0655
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          2.96
_diffrn_reflns_theta_max          24.99
_reflns_number_total              2849
_reflns_number_gt                 2008
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0000P)²+4.4414P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2849
_refine_ls_number_parameters      239
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1186
_refine_ls_R_factor_gt            0.0772
_refine_ls_wR_factor_ref          0.1628
_refine_ls_wR_factor_gt           0.1413
_refine_ls_goodness_of_fit_ref    1.104
_refine_ls_restrained_S_all       1.104
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
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_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.1451(5) 0.2253(3) 0.2618(2) 0.0226(8) Uani 1 1 d . . .
C2 C 0.1547(5) 0.1340(3) 0.2372(3) 0.0288(9) Uani 1 1 d . . .
H2 H 0.1922 0.1157 0.1803 0.035 Uiso 1 1 calc R . .
C3 C 0.1065(5) 0.0726(3) 0.3005(3) 0.0322(10) Uani 1 1 d . . .
H3 H 0.1113 0.0097 0.2870 0.039 Uiso 1 1 calc R . .
C4 C 0.0504(5) 0.0997(3) 0.3844(3) 0.0289(9) Uani 1 1 d . . .
H4 H 0.0193 0.0548 0.4263 0.035 Uiso 1 1 calc R . .
C5 C 0.0394(5) 0.1903(3) 0.4077(3) 0.0262(9) Uani 1 1 d . . .
H5 H -0.0004 0.2082 0.4642 0.031 Uiso 1 1 calc R . .
C6 C 0.0892(5) 0.2547(2) 0.3445(3) 0.0228(8) Uani 1 1 d . . .
C7 C 0.1027(5) 0.3511(2) 0.3413(2) 0.0214(8) Uani 1 1 d . . .
C8 C 0.2418(6) 0.3071(3) 0.1236(3) 0.0344(10) Uani 1 1 d . . .
H8A H 0.2608 0.3704 0.1071 0.052 Uiso 1 1 calc R . .
H8B H 0.1484 0.2804 0.0812 0.052 Uiso 1 1 calc R . .
H8C H 0.3544 0.2733 0.1208 0.052 Uiso 1 1 calc R . .
C9 C 0.0581(5) 0.4170(2) 0.4091(3) 0.0225(8) Uani 1 1 d . . .
N1 N 0.1852(4) 0.3027(2) 0.2151(2) 0.0252(7) Uani 1 1 d . . .
N2 N 0.1597(4) 0.3782(2) 0.2623(2) 0.0244(7) Uani 1 1 d . . .
O1 O -0.0091(4) 0.38801(18) 0.47895(17) 0.0289(7) Uani 1 1 d . . .
O2 O 0.0908(4) 0.50082(18) 0.39404(18) 0.0329(7) Uani 1 1 d . . .
H2O H 0.0677 0.5319 0.4391 0.039 Uiso 1 1 calc R . .
C10 C 0.6360(5) 0.2144(3) 0.2700(3) 0.0232(8) Uani 1 1 d . . .
C11 C 0.6902(5) 0.1793(3) 0.1886(3) 0.0295(10) Uani 1 1 d . . .
H11 H 0.6895 0.1161 0.1766 0.035 Uiso 1 1 calc R . .
C12 C 0.7444(5) 0.2413(3) 0.1273(3) 0.0295(10) Uani 1 1 d . . .
H12 H 0.7813 0.2204 0.0712 0.035 Uiso 1 1 calc R . .
C13 C 0.7465(5) 0.3344(3) 0.1454(3) 0.0278(9) Uani 1 1 d . . .
H13 H 0.7860 0.3748 0.1012 0.033 Uiso 1 1 calc R . .
C14 C 0.6937(5) 0.3695(3) 0.2246(2) 0.0244(9) Uani 1 1 d . . .
H14 H 0.6958 0.4329 0.2357 0.029 Uiso 1 1 calc R . .
C15 C 0.6363(5) 0.3085(3) 0.2887(2) 0.0231(8) Uani 1 1 d . . .
C16 C 0.5761(5) 0.3135(3) 0.3769(2) 0.0238(9) Uani 1 1 d . . .
C17 C 0.5616(6) 0.0753(3) 0.3593(3) 0.0337(10) Uani 1 1 d . . .
H17A H 0.6799 0.0508 0.3804 0.051 Uiso 1 1 calc R . .
H17B H 0.5181 0.0455 0.3025 0.051 Uiso 1 1 calc R . .
H17C H 0.4767 0.0642 0.4050 0.051 Uiso 1 1 calc R . .
C18 C 0.5461(5) 0.3938(3) 0.4324(2) 0.0234(8) Uani 1 1 d . . .
N3 N 0.5767(4) 0.1719(2) 0.3442(2) 0.0265(8) Uani 1 1 d . . .
N4 N 0.5403(4) 0.2307(2) 0.4093(2) 0.0266(8) Uani 1 1 d . . .
O3 O 0.5905(4) 0.46998(18) 0.39379(17) 0.0296(7) Uani 1 1 d . . .
H3O H 0.5679 0.5139 0.4270 0.035 Uiso 1 1 calc R . .
O4 O 0.4868(4) 0.38964(18) 0.50679(18) 0.0307(7) Uani 1 1 d . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
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 N1 1.381(5) . ?
C1 C6 1.398(5) . ?
C1 C2 1.400(5) . ?
C2 C3 1.375(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.428(5) . ?
C7 N2 1.341(5) . ?
C7 C9 1.457(5) . ?
C8 N1 1.456(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 O1 1.263(4) . ?
C9 O2 1.283(4) . ?
N1 N2 1.338(4) . ?
O2 H2O 0.8400 . ?
C10 N3 1.371(5) . ?
C10 C11 1.404(5) . ?
C10 C15 1.415(5) . ?
C11 C12 1.374(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.400(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.402(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.420(5) . ?
C16 N4 1.347(5) . ?
C16 C18 1.472(5) . ?
C17 N3 1.450(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 O4 1.223(4) . ?
C18 O3 1.317(4) . ?
N3 N4 1.343(4) . ?
O3 H3O 0.8400 . ?
 
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
N1 C1 C6 106.1(3) . . ?
N1 C1 C2 130.3(3) . . ?
C6 C1 C2 123.6(4) . . ?
C3 C2 C1 115.8(4) . . ?
C3 C2 H2 122.1 . . ?
C1 C2 H2 122.1 . . ?
C2 C3 C4 122.2(4) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C3 121.6(4) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 117.6(4) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 C7 104.6(3) . . ?
C5 C6 C7 136.0(4) . . ?
N2 C7 C6 110.8(3) . . ?
N2 C7 C9 120.7(3) . . ?
C6 C7 C9 128.4(3) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 O2 124.4(3) . . ?
O1 C9 C7 117.9(3) . . ?
O2 C9 C7 117.7(3) . . ?
N2 N1 C1 112.4(3) . . ?
N2 N1 C8 121.1(3) . . ?
C1 N1 C8 126.5(3) . . ?
N1 N2 C7 106.1(3) . . ?
C9 O2 H2O 109.5 . . ?
N3 C10 C11 131.0(3) . . ?
N3 C10 C15 106.7(3) . . ?
C11 C10 C15 122.3(4) . . ?
C12 C11 C10 116.4(4) . . ?
C12 C11 H11 121.8 . . ?
C10 C11 H11 121.8 . . ?
C11 C12 C13 121.7(4) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 122.3(4) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
C13 C14 C15 117.7(4) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
C14 C15 C10 119.5(3) . . ?
C14 C15 C16 136.8(4) . . ?
C10 C15 C16 103.6(3) . . ?
N4 C16 C15 111.6(3) . . ?
N4 C16 C18 119.2(3) . . ?
C15 C16 C18 129.2(3) . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 O3 124.0(3) . . ?
O4 C18 C16 123.1(3) . . ?
O3 C18 C16 112.9(3) . . ?
N4 N3 C10 112.3(3) . . ?
N4 N3 C17 120.2(3) . . ?
C10 N3 C17 127.4(3) . . ?
N3 N4 C16 105.8(3) . . ?
C18 O3 H3O 109.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              24.99
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.255
_refine_diff_density_min   -0.297
_refine_diff_density_rms    0.067
