#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/98/1519875.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_1519875
loop_
_publ_author_name
'Hursthouse, Michael B.'
'Huth, Susanne. L.'
'Withnell, J.'
_publ_section_title
;
 3-(Chloromethyl)-1-methyl-1H-indazole
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              283
_journal_year                    2007
_chemical_formula_sum            'C9 H9 Cl N2'
_chemical_formula_weight         180.63
_chemical_melting_point          62.5(15)
_chemical_name_systematic
;
 3-(Chloromethyl)-1-methyl-1H-indazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.0606(7)
_cell_length_b                   14.3262(7)
_cell_length_c                   8.1711(5)
_cell_measurement_reflns_used    3817
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1763.01(16)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_sigmaI/netI    0.0725
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13941
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.9564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            olourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0656
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0384P)²+3.1567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1497
_reflns_number_gt                2872
_reflns_number_total             3840
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-283.cif
_cod_data_source_block           2007jmw0004
_cod_depositor_comments
;
Citation :
Sample, Donated and Hursthouse, Michael B. and Huth, Susanne. L. and 
Withnell, J. (2007) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/283)

More at:
http://ecrystals.chem.soton.ac.uk/283/

The following automatic conversions were performed:

'_chemical_melting_point' value '61 - 64' was changed to '62.5(15)' -
the average value was taken and precision was estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1519875
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'
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 . . .
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'
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
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) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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) .
