#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/95/2239567.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_2239567
loop_
_publ_author_name
'Chicha, Hakima'
'Rakib, El Mostapha'
'Hannioui, Abdellah'
'Saadi, Mohamed'
'El Ammari, Lahcen'
_publ_section_title
;
 N-(3-Chloro-4-ethoxy-1-methyl-1H-indazol-5-yl)-4-methoxybenzenesulfonamide
;
_journal_coeditor_code           RZ5125
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o679
_journal_paper_doi               10.1107/S1600536814010800
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C17 H18 Cl N3 O4 S'
_chemical_formula_moiety         'C17 H18 Cl N3 O4 S'
_chemical_formula_sum            'C17 H18 Cl N3 O4 S'
_chemical_formula_weight         395.85
_chemical_melting_point          382
_chemical_name_systematic
N-(3-Chloro-4-ethoxy-1-methyl-1H-indazol-5-yl)-4-methoxybenzenesulfonamide
_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                91.810(6)
_cell_angle_beta                 102.566(5)
_cell_angle_gamma                100.514(5)
_cell_formula_units_Z            2
_cell_length_a                   8.5296(9)
_cell_length_b                   8.6165(9)
_cell_length_c                   12.9821(14)
_cell_measurement_reflns_used    4353
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.49
_cell_volume                     913.10(17)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'PLATON (Spek, 2009) and 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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 APEX Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20149
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.6934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.620
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0649P)²+0.4317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1282
_reflns_number_gt                3825
_reflns_number_total             4353
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            rz5125sup1.cif
_cod_data_source_block           I
_cod_database_code               2239567
_cod_database_fobs_code          2239567
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
C C1 0.5956(2) 1.2540(2) 0.53435(14) 0.0465(4) Uani d . 1 1
C C2 0.6304(2) 1.16538(19) 0.62328(12) 0.0362(3) Uani d . 1 1
C C3 0.4744(2) 1.0918(2) 0.63444(13) 0.0398(4) Uani d . 1 1
C C4 0.4514(2) 0.9921(2) 0.71502(15) 0.0442(4) Uani d . 1 1
H H4 0.3477 0.9433 0.7215 0.053 Uiso calc R 1 1
C C5 0.5905(2) 0.9706(2) 0.78353(14) 0.0415(4) Uani d . 1 1
H H5 0.5805 0.9040 0.8377 0.050 Uiso calc R 1 1
C C6 0.7494(2) 1.04510(19) 0.77578(12) 0.0360(3) Uani d . 1 1
C C7 0.77174(19) 1.14377(19) 0.69596(12) 0.0345(3) Uani d . 1 1
C C8 0.1867(2) 1.0920(3) 0.53266(18) 0.0650(6) Uani d . 1 1
H H8A 0.1396 1.1448 0.4730 0.098 Uiso calc R 1 1
H H8B 0.1465 1.1199 0.5929 0.098 Uiso calc R 1 1
H H8C 0.1567 0.9795 0.5164 0.098 Uiso calc R 1 1
C C9 1.0146(4) 1.3349(4) 0.7609(3) 0.1024(13) Uani d . 1 1
H H9A 1.0714 1.2835 0.8190 0.123 Uiso calc R 1 1
H H9B 0.9409 1.3902 0.7881 0.123 Uiso calc R 1 1
C C10 1.1304(4) 1.4471(4) 0.7272(3) 0.0911(10) Uani d . 1 1
H H10A 1.1881 1.5222 0.7854 0.137 Uiso calc R 1 1
H H10B 1.0757 1.5013 0.6710 0.137 Uiso calc R 1 1
H H10C 1.2066 1.3947 0.7023 0.137 Uiso calc R 1 1
C C11 0.8443(2) 0.6987(2) 0.84226(13) 0.0404(4) Uani d . 1 1
C C12 0.7169(2) 0.6368(2) 0.75581(14) 0.0463(4) Uani d . 1 1
H H12 0.7098 0.6828 0.6915 0.056 Uiso calc R 1 1
C C13 0.6019(3) 0.5074(2) 0.76605(16) 0.0497(4) Uani d . 1 1
H H13 0.5163 0.4665 0.7087 0.060 Uiso calc R 1 1
C C14 0.6129(2) 0.4373(2) 0.86199(16) 0.0468(4) Uani d . 1 1
C C15 0.7421(3) 0.4963(2) 0.94719(15) 0.0517(5) Uani d . 1 1
H H15 0.7518 0.4475 1.0106 0.062 Uiso calc R 1 1
C C16 0.8564(2) 0.6281(2) 0.93729(14) 0.0477(4) Uani d . 1 1
H H16 0.9417 0.6694 0.9947 0.057 Uiso calc R 1 1
C C17 0.4980(3) 0.2324(3) 0.9591(2) 0.0686(6) Uani d . 1 1
H H17A 0.4045 0.1478 0.9498 0.103 Uiso calc R 1 1
H H17B 0.4982 0.3051 1.0167 0.103 Uiso calc R 1 1
H H17C 0.5963 0.1898 0.9744 0.103 Uiso calc R 1 1
N N1 0.36396(19) 1.1398(2) 0.55635(13) 0.0501(4) Uani d . 1 1
N N2 0.4375(2) 1.2384(2) 0.49460(13) 0.0539(4) Uani d . 1 1
N N3 0.89007(18) 1.02121(17) 0.85304(11) 0.0404(3) Uani d . 1 1
H H3N 0.8863 1.0326 0.9184 0.048 Uiso d R 1 1
O O1 0.92080(15) 1.21799(16) 0.68322(10) 0.0452(3) Uani d . 1 1
O O2 1.01006(18) 0.87771(18) 0.73054(11) 0.0539(3) Uani d . 1 1
O O3 1.11721(16) 0.89209(18) 0.92468(11) 0.0527(3) Uani d . 1 1
O O4 0.4905(2) 0.31318(18) 0.86454(14) 0.0643(4) Uani d . 1 1
S S1 0.98089(5) 0.87464(5) 0.83452(3) 0.04091(13) Uani d . 1 1
Cl Cl1 0.73113(8) 1.37072(8) 0.47676(5) 0.0764(2) Uani d . 1 1
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'
Cl Cl 0.1484 0.1585 '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
N2 C1 C2 112.46(17)
N2 C1 Cl1 119.64(14)
C2 C1 Cl1 127.89(15)
C3 C2 C7 120.42(15)
C3 C2 C1 103.30(15)
C7 C2 C1 136.23(16)
N1 C3 C4 130.62(17)
N1 C3 C2 106.77(16)
C4 C3 C2 122.60(16)
C5 C4 C3 115.92(16)
C5 C4 H4 122.0
C3 C4 H4 122.0
C4 C5 C6 122.96(16)
C4 C5 H5 118.5
C6 C5 H5 118.5
C7 C6 C5 120.98(15)
C7 C6 N3 119.18(15)
C5 C6 N3 119.83(14)
O1 C7 C6 124.09(15)
O1 C7 C2 118.80(14)
C6 C7 C2 117.09(14)
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 C10 115.4(3)
O1 C9 H9A 108.4
C10 C9 H9A 108.4
O1 C9 H9B 108.4
C10 C9 H9B 108.4
H9A C9 H9B 107.5
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C16 C11 C12 120.00(18)
C16 C11 S1 119.51(14)
C12 C11 S1 120.31(13)
C13 C12 C11 119.71(17)
C13 C12 H12 120.1
C11 C12 H12 120.1
C12 C13 C14 120.31(18)
C12 C13 H13 119.8
C14 C13 H13 119.8
O4 C14 C15 124.41(18)
O4 C14 C13 115.58(18)
C15 C14 C13 120.01(18)
C16 C15 C14 119.60(17)
C16 C15 H15 120.2
C14 C15 H15 120.2
C15 C16 C11 120.33(18)
C15 C16 H16 119.8
C11 C16 H16 119.8
O4 C17 H17A 109.5
O4 C17 H17B 109.5
H17A C17 H17B 109.5
O4 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
N2 N1 C3 111.91(15)
N2 N1 C8 120.44(17)
C3 N1 C8 127.59(19)
C1 N2 N1 105.56(15)
C6 N3 S1 120.30(12)
C6 N3 H3N 116.8
S1 N3 H3N 110.2
C7 O1 C9 118.21(16)
C14 O4 C17 118.35(19)
O2 S1 O3 119.64(9)
O2 S1 N3 108.12(8)
O3 S1 N3 104.44(8)
O2 S1 C11 108.74(9)
O3 S1 C11 108.06(8)
N3 S1 C11 107.20(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.315(3)
C1 C2 1.412(2)
C1 Cl1 1.705(2)
C2 C3 1.406(2)
C2 C7 1.406(2)
C3 N1 1.356(2)
C3 C4 1.399(3)
C4 C5 1.366(3)
C4 H4 0.9300
C5 C6 1.416(2)
C5 H5 0.9300
C6 C7 1.384(2)
C6 N3 1.438(2)
C7 O1 1.3618(19)
C8 N1 1.454(3)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 O1 1.401(3)
C9 C10 1.403(3)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 C16 1.385(2)
C11 C12 1.395(3)
C11 S1 1.7552(19)
C12 C13 1.374(3)
C12 H12 0.9300
C13 C14 1.394(3)
C13 H13 0.9300
C14 O4 1.358(3)
C14 C15 1.388(3)
C15 C16 1.384(3)
C15 H15 0.9300
C16 H16 0.9300
C17 O4 1.425(3)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
N1 N2 1.351(2)
N3 S1 1.6346(15)
N3 H3N 0.8599
O2 S1 1.4249(14)
O3 S1 1.4414(13)
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
N3 H3N O3 2_777 0.86 2.13 2.974(2) 169.0
