 
data_2007jmw0004

#merohedral twin 
#twin law: 100 0-10 00-1

_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 3-(Chloromethyl)-1-methyl-1H-indazole
;
_chemical_name_common             ?
_chemical_melting_point           '61 - 64'
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C9 H9 Cl N2'
_chemical_formula_weight          180.63
 
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'
 'Cl'  'Cl'   0.1484   0.1585
 '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'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P2(1)/c
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    15.0606(7)
_cell_length_b                    14.3262(7)
_cell_length_c                    8.1711(5)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1763.01(16)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     3817
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             olourless
_exptl_crystal_size_max           0.12
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.361
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              752
_exptl_absorpt_coefficient_mu     0.375
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9564
_exptl_absorpt_correction_T_max   0.9925
_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             13941
_diffrn_reflns_av_R_equivalents   0.0723
_diffrn_reflns_av_sigmaI/netI     0.0725
_diffrn_reflns_limit_h_min        -17
_diffrn_reflns_limit_h_max        19
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        18
_diffrn_reflns_limit_l_min        -10
_diffrn_reflns_limit_l_max        10
_diffrn_reflns_theta_min          3.06
_diffrn_reflns_theta_max          27.50
_reflns_number_total              3840
_reflns_number_gt                 2872
_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)+(0.0384P)²+3.1567P] 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          3840
_refine_ls_number_parameters      220
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0958
_refine_ls_R_factor_gt            0.0656
_refine_ls_wR_factor_ref          0.1497
_refine_ls_wR_factor_gt           0.1321
_refine_ls_goodness_of_fit_ref    1.057
_refine_ls_restrained_S_all       1.057
_refine_ls_shift/su_max           0.029
_refine_ls_shift/su_mean          0.004
 
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 0.4196(3) 0.1634(3) 0.5535(6) 0.0245(10) Uani 1 1 d . . .
C2 C 0.5069(3) 0.1530(3) 0.6213(6) 0.0259(10) Uani 1 1 d . . .
C3 C 0.5484(3) 0.1732(3) 0.7720(6) 0.0269(10) Uani 1 1 d . . .
H3 H 0.5163 0.2003 0.8601 0.032 Uiso 1 1 calc R . .
C4 C 0.6370(3) 0.1522(3) 0.7869(6) 0.0313(11) Uani 1 1 d . . .
H4 H 0.6664 0.1644 0.8875 0.038 Uiso 1 1 calc R . .
C5 C 0.6852(3) 0.1133(3) 0.6566(7) 0.0344(12) Uani 1 1 d . . .
H5 H 0.7466 0.1006 0.6713 0.041 Uiso 1 1 calc R . .
C6 C 0.6464(3) 0.0931(3) 0.5085(6) 0.0305(11) Uani 1 1 d . . .
H6 H 0.6794 0.0665 0.4211 0.037 Uiso 1 1 calc R . .
C7 C 0.5564(3) 0.1135(3) 0.4929(6) 0.0272(10) Uani 1 1 d . . .
C8 C 0.3397(3) 0.2020(3) 0.6339(6) 0.0260(10) Uani 1 1 d . . .
H8A H 0.2924 0.2110 0.5513 0.031 Uiso 1 1 calc R . .
H8B H 0.3540 0.2638 0.6815 0.031 Uiso 1 1 calc R . .
C9 C 0.5190(3) 0.0739(3) 0.1992(6) 0.0349(12) Uani 1 1 d . . .
H9A H 0.5267 0.1292 0.1301 0.052 Uiso 1 1 calc R . .
H9B H 0.4699 0.0360 0.1570 0.052 Uiso 1 1 calc R . .
H9C H 0.5738 0.0369 0.1981 0.052 Uiso 1 1 calc R . .
C10 C -0.0794(3) 0.1641(3) 0.3825(6) 0.0244(10) Uani 1 1 d . . .
C11 C 0.0073(3) 0.1542(3) 0.3162(5) 0.0216(9) Uani 1 1 d . . .
C12 C 0.0467(3) 0.1694(3) 0.1639(6) 0.0272(10) Uani 1 1 d . . .
H12 H 0.0137 0.1945 0.0753 0.033 Uiso 1 1 calc R . .
C13 C 0.1354(3) 0.1468(3) 0.1461(6) 0.0321(11) Uani 1 1 d . . .
H13 H 0.1634 0.1557 0.0431 0.039 Uiso 1 1 calc R . .
C14 C 0.1851(3) 0.1105(3) 0.2789(6) 0.0329(11) Uani 1 1 d . . .
H14 H 0.2462 0.0966 0.2629 0.040 Uiso 1 1 calc R . .
C15 C 0.1483(3) 0.0948(3) 0.4288(6) 0.0287(11) Uani 1 1 d . . .
H15 H 0.1822 0.0700 0.5167 0.034 Uiso 1 1 calc R . .
C16 C 0.0576(3) 0.1171(3) 0.4477(6) 0.0226(10) Uani 1 1 d . . .
C17 C -0.1613(3) 0.2004(3) 0.3024(6) 0.0283(10) Uani 1 1 d . . .
H17A H -0.1491 0.2622 0.2531 0.034 Uiso 1 1 calc R . .
H17B H -0.2088 0.2081 0.3852 0.034 Uiso 1 1 calc R . .
C18 C 0.0237(3) 0.0834(3) 0.7420(6) 0.0338(12) Uani 1 1 d . . .
H18A H 0.0580 0.0253 0.7426 0.051 Uiso 1 1 calc R . .
H18B H -0.0312 0.0746 0.8047 0.051 Uiso 1 1 calc R . .
H18C H 0.0589 0.1335 0.7917 0.051 Uiso 1 1 calc R . .
Cl1 Cl 0.30007(9) 0.12526(8) 0.79344(15) 0.0354(3) Uani 1 1 d . . .
Cl2 Cl -0.19814(9) 0.11936(9) 0.14391(15) 0.0386(3) Uani 1 1 d . . .
N1 N 0.4996(3) 0.1025(3) 0.3644(5) 0.0258(9) Uani 1 1 d . . .
N2 N 0.4162(3) 0.1340(3) 0.4004(5) 0.0258(9) Uani 1 1 d . . .
N3 N 0.0020(3) 0.1081(3) 0.5760(5) 0.0293(9) Uani 1 1 d . . .
N4 N -0.0818(3) 0.1375(3) 0.5365(5) 0.0276(9) 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 N2 1.321(6) . ?
C1 C2 1.435(6) . ?
C1 C8 1.479(6) . ?
C2 C7 1.406(7) . ?
C2 C3 1.411(7) . ?
C3 C4 1.373(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.403(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(6) . ?
C6 H6 0.9500 . ?
C7 N1 1.363(6) . ?
C8 Cl1 1.807(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.441(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N4 1.316(6) . ?
C10 C11 1.420(6) . ?
C10 C17 1.490(6) . ?
C11 C12 1.396(6) . ?
C11 C16 1.418(6) . ?
C12 C13 1.381(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.418(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.363(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.411(6) . ?
C15 H15 0.9500 . ?
C16 N3 1.348(6) . ?
C17 Cl2 1.825(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 N3 1.440(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N1 N2 1.366(5) . ?
N3 N4 1.369(6) . ?
 
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 111.6(4) . . ?
N2 C1 C8 120.6(4) . . ?
C2 C1 C8 127.8(4) . . ?
C7 C2 C3 120.0(4) . . ?
C7 C2 C1 103.8(4) . . ?
C3 C2 C1 136.2(4) . . ?
C4 C3 C2 117.6(5) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 121.5(5) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 122.1(4) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 116.7(5) . . ?
C5 C6 H6 121.6 . . ?
C7 C6 H6 121.6 . . ?
N1 C7 C6 131.1(5) . . ?
N1 C7 C2 106.8(4) . . ?
C6 C7 C2 122.1(5) . . ?
C1 C8 Cl1 111.2(3) . . ?
C1 C8 H8A 109.4 . . ?
Cl1 C8 H8A 109.4 . . ?
C1 C8 H8B 109.4 . . ?
Cl1 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 C11 111.2(4) . . ?
N4 C10 C17 119.9(4) . . ?
C11 C10 C17 129.0(4) . . ?
C12 C11 C16 120.4(4) . . ?
C12 C11 C10 135.7(4) . . ?
C16 C11 C10 103.9(4) . . ?
C13 C12 C11 118.0(4) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C12 C13 C14 121.1(4) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 122.2(4) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C14 C15 C16 117.0(4) . . ?
C14 C15 H15 121.5 . . ?
C16 C15 H15 121.5 . . ?
N3 C16 C15 131.7(4) . . ?
N3 C16 C11 107.0(4) . . ?
C15 C16 C11 121.3(4) . . ?
C10 C17 Cl2 110.0(3) . . ?
C10 C17 H17A 109.7 . . ?
Cl2 C17 H17A 109.7 . . ?
C10 C17 H17B 109.7 . . ?
Cl2 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 N1 N2 111.9(4) . . ?
C7 N1 C9 128.8(4) . . ?
N2 N1 C9 118.8(4) . . ?
C1 N2 N1 105.9(4) . . ?
C16 N3 N4 111.1(4) . . ?
C16 N3 C18 128.0(4) . . ?
N4 N3 C18 120.4(4) . . ?
C10 N4 N3 106.8(4) . . ?
 
_diffrn_measured_fraction_theta_max    0.945
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.945
_refine_diff_density_max    0.461
_refine_diff_density_min   -0.356
_refine_diff_density_rms    0.079
