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# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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data_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 2-(4-methoxybenzyl)-2H-indazole
;
_chemical_name_common            ?
_chemical_melting_point          116-118
_chemical_formula_moiety         'C15 H14 N2 O'
_chemical_formula_sum            'C15 H14 N2 O'
_chemical_formula_weight         238.28

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.4150(16)
_cell_length_b                   5.6395(9)
_cell_length_c                   12.3566(18)
_cell_angle_alpha                90
_cell_angle_beta                 110.273(18)
_cell_angle_gamma                90
_cell_volume                     615.44(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.652
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82368
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
_exptl_special_details
;


_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2239
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.814
_diffrn_reflns_theta_max         70.672
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.701
_diffrn_reflns_point_group_measured_fraction_full 0.722
_reflns_number_total             1654
_reflns_number_gt                1425
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.298
_reflns_Friedel_fraction_max     0.362
_reflns_Friedel_fraction_full    0.380

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0545P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 335 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1654
_refine_ls_number_parameters     165
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7382(3) 0.1090(5) 0.53885(19) 0.0579(7) Uani 1 1 d . . . . .
O1 O 0.7611(2) 0.7341(5) 0.98013(18) 0.0750(7) Uani 1 1 d . . . . .
C2 C 0.8430(3) 0.0865(6) 0.4063(2) 0.0549(7) Uani 1 1 d . . . . .
C7 C 0.7583(3) 0.2981(6) 0.3967(2) 0.0527(7) Uani 1 1 d . . . . .
C14 C 0.5851(3) 0.3933(7) 0.7130(2) 0.0664(9) Uani 1 1 d . . . . .
H14 H 0.4958 0.3882 0.6496 0.080 Uiso 1 1 calc R U . . .
N2 N 0.6935(3) 0.3115(5) 0.4780(2) 0.0593(6) Uani 1 1 d . . . . .
C9 C 0.6970(3) 0.2329(6) 0.7194(2) 0.0588(8) Uani 1 1 d . . . . .
C1 C 0.8258(3) -0.0286(6) 0.5005(2) 0.0601(7) Uani 1 1 d . . . . .
H1 H 0.8674 -0.1740 0.5310 0.072 Uiso 1 1 calc R U . . .
C13 C 0.5997(3) 0.5625(7) 0.7972(2) 0.0657(9) Uani 1 1 d . . . . .
H13 H 0.5213 0.6684 0.7904 0.079 Uiso 1 1 calc R U . . .
C6 C 0.7471(3) 0.4609(6) 0.3069(2) 0.0625(8) Uani 1 1 d . . . . .
H6 H 0.6918 0.6004 0.2994 0.075 Uiso 1 1 calc R U . . .
C4 C 0.9047(4) 0.1984(7) 0.2416(3) 0.0687(9) Uani 1 1 d . . . . .
H4 H 0.9526 0.1686 0.1886 0.082 Uiso 1 1 calc R U . . .
C3 C 0.9178(3) 0.0386(6) 0.3280(3) 0.0652(9) Uani 1 1 d . . . . .
H3 H 0.9750 -0.0987 0.3348 0.078 Uiso 1 1 calc R U . . .
C10 C 0.8305(3) 0.2457(7) 0.8158(3) 0.0665(9) Uani 1 1 d . . . . .
H10 H 0.9085 0.1389 0.8229 0.080 Uiso 1 1 calc R U . . .
C11 C 0.8478(3) 0.4139(7) 0.9001(2) 0.0670(9) Uani 1 1 d . . . . .
H11 H 0.9377 0.4207 0.9628 0.080 Uiso 1 1 calc R U . . .
C12 C 0.7332(3) 0.5723(7) 0.8924(2) 0.0595(8) Uani 1 1 d . . . . .
C5 C 0.8191(4) 0.4082(7) 0.2323(3) 0.0687(9) Uani 1 1 d . . . . .
H5 H 0.8120 0.5136 0.1728 0.082 Uiso 1 1 calc R U . . .
C8 C 0.6760(4) 0.0446(8) 0.6288(3) 0.0713(10) Uani 1 1 d . . . . .
H8A H 0.7243 -0.1003 0.6660 0.086 Uiso 1 1 calc R U . . .
H8B H 0.5686 0.0124 0.5926 0.086 Uiso 1 1 calc R U . . .
C15 C 0.6422(4) 0.8907(8) 0.9796(3) 0.0859(11) Uani 1 1 d . . . . .
H15A H 0.6147 0.9882 0.9118 0.129 Uiso 1 1 calc R U . . .
H15B H 0.6759 0.9895 1.0471 0.129 Uiso 1 1 calc R U . . .
H15C H 0.5560 0.8000 0.9797 0.129 Uiso 1 1 calc R U . . .


_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
N1 C1 1.333(4) . ?
N1 N2 1.352(4) . ?
N1 C8 1.470(4) . ?
O1 C12 1.371(4) . ?
O1 C15 1.424(4) . ?
C2 C1 1.391(4) . ?
C2 C3 1.405(4) . ?
C2 C7 1.417(4) . ?
C7 N2 1.346(3) . ?
C7 C6 1.415(4) . ?
C14 C9 1.370(5) . ?
C14 C13 1.383(5) . ?
C9 C10 1.403(4) . ?
C9 C8 1.506(5) . ?
C13 C12 1.394(4) . ?
C6 C5 1.353(4) . ?
C4 C3 1.370(5) . ?
C4 C5 1.414(5) . ?
C10 C11 1.375(5) . ?
C11 C12 1.379(5) . ?

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
C1 N1 N2 113.9(2) . . ?
C1 N1 C8 125.6(3) . . ?
N2 N1 C8 120.0(3) . . ?
C12 O1 C15 118.3(3) . . ?
C1 C2 C3 135.9(3) . . ?
C1 C2 C7 103.7(2) . . ?
C3 C2 C7 120.4(3) . . ?
N2 C7 C6 128.2(3) . . ?
N2 C7 C2 111.9(3) . . ?
C6 C7 C2 119.9(3) . . ?
C9 C14 C13 122.6(3) . . ?
C7 N2 N1 103.5(3) . . ?
C14 C9 C10 117.4(3) . . ?
C14 C9 C8 121.5(3) . . ?
C10 C9 C8 121.1(3) . . ?
N1 C1 C2 107.0(3) . . ?
C14 C13 C12 119.2(3) . . ?
C5 C6 C7 118.2(3) . . ?
C3 C4 C5 120.6(3) . . ?
C4 C3 C2 118.6(3) . . ?
C11 C10 C9 121.0(3) . . ?
C10 C11 C12 120.7(3) . . ?
O1 C12 C11 116.5(3) . . ?
O1 C12 C13 124.3(3) . . ?
C11 C12 C13 119.2(3) . . ?
C6 C5 C4 122.3(3) . . ?
N1 C8 C9 113.8(3) . . ?

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 994876'
