#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/08/2230809.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230809
loop_
_publ_author_name
'Abbassi, Najat'
'Rakib, El Mostapha'
'Zouihri, Hafid'
_publ_section_title
;
 N-[7-Ethoxy-1-(prop-2-en-1-yl)-1H-indazol-4-yl]-4-methylbenzenesulfonamide
;
_journal_coeditor_code           NG5164
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1561
_journal_paper_doi               10.1107/S1600536811019465
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H21 N3 O3 S'
_chemical_formula_moiety         'C19 H21 N3 O3 S'
_chemical_formula_sum            'C19 H21 N3 O3 S'
_chemical_formula_weight         371.45
_chemical_name_systematic
;
N-[7-Ethoxy-1-(prop-2-en-1-yl)-1H-indazol-4-yl]-4-
methylbenzenesulfonamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.814(2)
_cell_angle_beta                 92.346(2)
_cell_angle_gamma                107.500(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2208(3)
_cell_length_b                   10.4985(4)
_cell_length_c                   11.9655(5)
_cell_measurement_pressure       101
_cell_measurement_reflns_used    341
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.5
_cell_volume                     921.33(6)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23139
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.315
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3629
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.327
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0530P)²+0.4364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1178
_reflns_number_gt                3281
_reflns_number_total             3629
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng5164.cif
_cod_data_source_block           I
_cod_database_code               2230809
_cod_database_fobs_code          2230809
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.1369(3) 0.4744(3) 0.2566(2) 0.0518(6) Uani d . 1 1 A 4
C C10 0.4698(3) 0.9705(2) 0.33160(18) 0.0362(4) Uani d . 1 1 A 4
C C11 0.5617(2) 0.8894(2) 0.36197(17) 0.0345(4) Uani d . 1 1 A 4
C C12 0.4804(3) 0.7709(2) 0.39361(17) 0.0346(4) Uani d . 1 1 A 4
C C13 0.6165(3) 0.7239(3) 0.4207(2) 0.0444(5) Uani d . 1 1 A 4
C C14 0.8737(3) 1.0072(3) 0.3443(2) 0.0574(7) Uani d D 1 1 A .
C C15 0.4773(4) 1.1700(3) 0.2738(3) 0.0595(7) Uani d . 1 1 . .
C C16 0.4069(5) 1.1104(4) 0.1447(3) 0.0873(10) Uani d . 1 1 A .
C C17A 0.8898(7) 0.9302(9) 0.2134(5) 0.0553(16) Uani d PD 0.622(10) 1 A 1
C C17B 0.9147(12) 1.0054(12) 0.2270(8) 0.057(3) Uani d PD 0.378(10) 1 A 2
C C18A 0.8938(10) 0.9902(9) 0.1303(6) 0.101(3) Uani d PD 0.622(10) 1 A 1
C C18B 0.8493(13) 0.8767(12) 0.1399(10) 0.079(4) Uani d PD 0.378(10) 1 A 2
C C19 -0.3856(5) 0.3527(4) -0.0543(3) 0.0891(11) Uani d . 1 1 . .
C C2 -0.2614(4) 0.4503(3) 0.1640(2) 0.0587(7) Uani d . 1 1 A 4
C C3 -0.2476(4) 0.3819(3) 0.0462(2) 0.0596(7) Uani d . 1 1 A 4
C C4 -0.1046(4) 0.3413(3) 0.0237(2) 0.0697(8) Uani d . 1 1 A 4
C C5 0.0215(4) 0.3650(3) 0.1146(2) 0.0595(7) Uani d . 1 1 A 4
C C6 0.0038(3) 0.4302(2) 0.2315(2) 0.0422(5) Uani d . 1 1 A 4
C C7 0.3012(3) 0.7306(2) 0.39635(17) 0.0348(4) Uani d . 1 1 A 4
C C8 0.2116(3) 0.8081(2) 0.36507(19) 0.0395(5) Uani d . 1 1 A 4
C C9 0.2950(3) 0.9261(2) 0.3323(2) 0.0408(5) Uani d . 1 1 A 4
H H1 -0.1478 0.5201 0.3352 0.062 Uiso calc R 1 1 A 4
H H13 0.6020 0.6459 0.4448 0.053 Uiso calc R 1 1 A 4
H H14A 0.9800 1.0318 0.3969 0.069 Uiso calc R 1 1 B 1
H H14B 0.8479 1.0937 0.3523 0.069 Uiso calc R 1 1 B 1
H H15A 0.5564 1.2664 0.2933 0.071 Uiso calc R 1 1 A 4
H H15B 0.3835 1.1747 0.3199 0.071 Uiso calc R 1 1 A 4
H H16A 0.4981 1.0999 0.0987 0.131 Uiso calc R 1 1 . .
H H16B 0.3571 1.1738 0.1251 0.131 Uiso calc R 1 1 . .
H H16C 0.3198 1.0189 0.1266 0.131 Uiso calc R 1 1 . .
H H17A 0.8970 0.8388 0.1918 0.066 Uiso calc PR 0.622(10) 1 A 1
H H17B 0.9807 1.0864 0.2132 0.069 Uiso calc PR 0.378(10) 1 A 2
H H18A 0.8868 1.0814 0.1503 0.121 Uiso calc PR 0.622(10) 1 A 1
H H18B 0.9036 0.9407 0.0523 0.121 Uiso calc PR 0.622(10) 1 A 1
H H18C 0.7840 0.7984 0.1577 0.095 Uiso calc PR 0.378(10) 1 A 2
H H18D 0.8694 0.8659 0.0620 0.095 Uiso calc PR 0.378(10) 1 A 2
H H19A -0.3360 0.3474 -0.1263 0.134 Uiso calc R 1 1 A 4
H H19B -0.4341 0.4283 -0.0346 0.134 Uiso calc R 1 1 A 4
H H19C -0.4746 0.2638 -0.0662 0.134 Uiso calc R 1 1 A 4
H H2 -0.3559 0.4805 0.1810 0.070 Uiso calc R 1 1 A 4
H H3 0.146(3) 0.630(3) 0.484(2) 0.049 Uiso d . 1 1 . .
H H4 -0.0927 0.2968 -0.0549 0.084 Uiso calc R 1 1 A 4
H H5 0.1176 0.3372 0.0973 0.071 Uiso calc R 1 1 A 4
H H8 0.0931 0.7822 0.3655 0.047 Uiso calc R 1 1 A 4
H H9 0.2298 0.9753 0.3105 0.049 Uiso calc R 1 1 A 4
N N1 0.7663(2) 0.8046(2) 0.40729(19) 0.0497(5) Uani d . 1 1 A .
N N2 0.7338(2) 0.9065(2) 0.37229(17) 0.0424(4) Uani d . 1 1 . .
N N3 0.2190(2) 0.61730(19) 0.43869(17) 0.0405(4) Uani d . 1 1 . .
O O1 0.5640(2) 1.08767(18) 0.30610(17) 0.0553(4) Uani d . 1 1 A 4
O O2 0.3035(2) 0.42371(19) 0.29865(18) 0.0590(5) Uani d . 1 1 . .
O O3 0.0727(2) 0.37090(18) 0.41924(17) 0.0571(5) Uani d . 1 1 . .
S S1 0.15828(7) 0.45175(6) 0.34923(5) 0.04300(19) Uani d . 1 1 A 4
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'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 H1 . . 120.3 ?
C6 C1 H1 . . 120.3 ?
C6 C1 C2 . . 119.5(2) ?
O1 C10 C11 . . 117.06(18) ?
C9 C10 C11 . . 116.67(19) ?
C9 C10 O1 . . 126.26(19) ?
C12 C11 C10 . . 122.13(18) ?
N2 C11 C10 . . 131.2(2) ?
N2 C11 C12 . . 106.64(18) ?
C7 C12 C13 . . 136.1(2) ?
C11 C12 C13 . . 104.30(18) ?
C11 C12 C7 . . 119.59(18) ?
C12 C13 H13 . . 124.3 ?
N1 C13 H13 . . 124.3 ?
N1 C13 C12 . . 111.4(2) ?
H14A C14 H14B . . 108.8 ?
C17A C14 H14B . . 110.7 ?
C17B C14 H14B . . 86.7 ?
N2 C14 H14B . . 110.7 ?
C17A C14 H14A . . 110.7 ?
C17B C14 H14A . . 108.8 ?
N2 C14 H14A . . 110.7 ?
C17B C14 C17A . . 27.3(3) ?
N2 C14 C17A . . 105.1(3) ?
N2 C14 C17B . . 127.8(5) ?
H15A C15 H15B . . 107.9 ?
C16 C15 H15B . . 109.2 ?
O1 C15 H15B . . 109.2 ?
C16 C15 H15A . . 109.2 ?
O1 C15 H15A . . 109.2 ?
O1 C15 C16 . . 112.1(3) ?
H16B C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16B . . 109.5 ?
C15 C16 H16A . . 109.5 ?
C14 C17A H17A . . 118.9 ?
C18A C17A H17A . . 118.9 ?
C18A C17A C14 . . 122.3(7) ?
C14 C17B H17B . . 122.8 ?
C18B C17B H17B . . 122.8 ?
C18B C17B C14 . . 114.3(9) ?
H18A C18A H18B . . 120.0 ?
C17A C18A H18B . . 120.0 ?
C17A C18A H18A . . 120.0 ?
H18C C18B H18D . . 120.0 ?
C17B C18B H18D . . 120.0 ?
C17B C18B H18C . . 120.0 ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C1 C2 C3 . . 121.1(3) ?
C2 C3 C19 . . 120.9(3) ?
C4 C3 C19 . . 120.9(3) ?
C4 C3 C2 . . 118.2(3) ?
C5 C4 H4 . . 119.1 ?
C3 C4 H4 . . 119.1 ?
C3 C4 C5 . . 121.7(3) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C4 C5 C6 . . 119.4(3) ?
C1 C6 S1 . . 120.01(17) ?
C5 C6 S1 . . 119.80(19) ?
C5 C6 C1 . . 120.2(2) ?
C12 C7 N3 . . 120.09(18) ?
C8 C7 N3 . . 121.55(18) ?
C8 C7 C12 . . 118.23(19) ?
C9 C8 H8 . . 119.3 ?
C7 C8 H8 . . 119.3 ?
C7 C8 C9 . . 121.47(19) ?
C8 C9 H9 . . 119.1 ?
C10 C9 H9 . . 119.1 ?
C10 C9 C8 . . 121.89(19) ?
C13 N1 N2 . . 106.45(17) ?
C11 N2 C14 . . 129.6(2) ?
N1 N2 C14 . . 119.12(19) ?
N1 N2 C11 . . 111.18(18) ?
S1 N3 H3 . . 110.4(19) ?
C7 N3 H3 . . 116.7(18) ?
C7 N3 S1 . . 120.46(15) ?
C10 O1 C15 . . 118.87(19) ?
N3 S1 C6 . . 107.93(10) ?
O3 S1 C6 . . 108.09(11) ?
O2 S1 C6 . . 107.73(11) ?
O3 S1 N3 . . 104.80(10) ?
O2 S1 N3 . . 108.66(11) ?
O2 S1 O3 . . 119.18(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 H1 . 0.9300 ?
C1 C2 . 1.382(4) ?
C10 O1 . 1.376(3) ?
C10 C9 . 1.372(3) ?
C11 C10 . 1.412(3) ?
C11 C12 . 1.401(3) ?
C11 N2 . 1.366(3) ?
C12 C13 . 1.417(3) ?
C13 H13 . 0.9300 ?
C13 N1 . 1.317(3) ?
C14 H14B . 0.9700 ?
C14 H14A . 0.9700 ?
C14 C17A . 1.546(7) ?
C14 C17B . 1.453(8) ?
C15 H15B . 0.9700 ?
C15 H15A . 0.9700 ?
C15 C16 . 1.483(4) ?
C16 H16C . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16A . 0.9600 ?
C17A H17A . 0.9300 ?
C17A C18A . 1.335(8) ?
C17B H17B . 0.9300 ?
C18A H18B . 0.9300 ?
C18A H18A . 0.9300 ?
C18B H18D . 0.9300 ?
C18B H18C . 0.9300 ?
C18B C17B . 1.345(12) ?
C19 H19C . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19A . 0.9600 ?
C2 H2 . 0.9300 ?
C2 C3 . 1.388(4) ?
C3 C19 . 1.506(4) ?
C3 C4 . 1.374(4) ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C5 C4 . 1.378(4) ?
C6 C1 . 1.381(3) ?
C6 C5 . 1.380(3) ?
C7 N3 . 1.436(3) ?
C7 C12 . 1.410(3) ?
C7 C8 . 1.370(3) ?
C8 H8 . 0.9300 ?
C8 C9 . 1.408(3) ?
C9 H9 . 0.9300 ?
N2 C14 . 1.443(3) ?
N2 N1 . 1.358(3) ?
N3 H3 . 0.84(3) ?
O1 C15 . 1.403(3) ?
S1 C6 . 1.767(2) ?
S1 N3 . 1.6280(19) ?
S1 O3 . 1.4369(17) ?
S1 O2 . 1.4260(18) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_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
N3 H3 O3 2_566 0.86(2) 2.15(2) 3.002(2) 171(2) yes
C5 H5 O2 . 0.93 2.53 2.908(3) 104 ?
C14 H14B O1 . 0.97 2.35 2.974(2) 121 yes
C19 H19C Cg1 2_565 0.96 2.87 3.622(2) 136 yes
