#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:24:10 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296651 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/34/7063454.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_7063454
loop_
_publ_author_name
'Kumar, Sandeep'
'Gupta, Ashis Kumar'
'Vaishanv, Narendra Kumar'
'Kant, Ruchir'
'Mohanan, Kishor'
_publ_section_title
;
 CsF-mediated reaction of diazo compounds with 3-nitroindoles: access to
 cyano- and phosphonylpyrazolo[4,3-b]indoles
;
_journal_issue                   40
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17670
_journal_page_last               17675
_journal_paper_doi               10.1039/D4NJ03266G
_journal_volume                  48
_journal_year                    2024
_chemical_formula_sum            'C16 H9 Cl N4 O2 S'
_chemical_formula_weight         356.78
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_audit_creation_method           SHELXL-97
_audit_update_record
;
2024-02-15 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.3474(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9488(2)
_cell_length_b                   15.2489(5)
_cell_length_c                   9.43379(19)
_cell_measurement_reflns_used    7105
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      76.8940
_cell_measurement_theta_min      4.0670
_cell_volume                     1565.38(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11102
_diffrn_reflns_theta_full        77.55
_diffrn_reflns_theta_max         77.55
_diffrn_reflns_theta_min         4.06
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.566
_exptl_absorpt_correction_T_max  0.9321
_exptl_absorpt_correction_T_min  0.7884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0404
_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)+(0.0482P)²+0.4532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                2739
_reflns_number_total             3110
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4nj03266g2.cif
_cod_data_source_block           xxx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7063454--7063455.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7063454
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 0.70847(16) 1.00057(12) 0.05510(18) 0.0497(4) Uani 1 1 d . . .
C2 C 0.80424(19) 0.98288(15) -0.0256(2) 0.0620(5) Uani 1 1 d . . .
H2 H 0.8323 0.9260 -0.0363 0.074 Uiso 1 1 calc R . .
C3 C 0.8559(2) 1.05281(17) -0.0891(2) 0.0704(6) Uani 1 1 d . . .
H3 H 0.9213 1.0429 -0.1421 0.085 Uiso 1 1 calc R . .
C4 C 0.8132(2) 1.13759(17) -0.0762(2) 0.0722(6) Uani 1 1 d . . .
H4 H 0.8493 1.1831 -0.1224 0.087 Uiso 1 1 calc R . .
C5 C 0.7186(2) 1.15594(14) 0.0034(2) 0.0632(5) Uani 1 1 d . . .
H5 H 0.6906 1.2131 0.0117 0.076 Uiso 1 1 calc R . .
C6 C 0.66582(16) 1.08671(12) 0.07145(19) 0.0500(4) Uani 1 1 d . . .
C7 C 0.57019(16) 1.07872(12) 0.16324(19) 0.0506(4) Uani 1 1 d . . .
C8 C 0.45976(17) 0.99158(13) 0.2871(2) 0.0557(4) Uani 1 1 d . . .
C9 C 0.55534(15) 0.99267(12) 0.19929(19) 0.0483(4) Uani 1 1 d . . .
C10 C 0.4031(2) 0.92300(16) 0.3594(2) 0.0671(5) Uani 1 1 d . . .
C11 C 0.79781(16) 0.85552(11) 0.32046(19) 0.0483(4) Uani 1 1 d . . .
C12 C 0.76759(18) 0.88642(13) 0.4494(2) 0.0576(5) Uani 1 1 d . . .
H12 H 0.6863 0.8991 0.4613 0.069 Uiso 1 1 calc R . .
C13 C 0.8583(2) 0.89836(15) 0.5598(2) 0.0655(5) Uani 1 1 d . . .
H13 H 0.8392 0.9192 0.6473 0.079 Uiso 1 1 calc R . .
C14 C 0.97792(19) 0.87919(15) 0.5396(2) 0.0632(5) Uani 1 1 d . . .
C15 C 1.00904(19) 0.84771(18) 0.4120(3) 0.0742(6) Uani 1 1 d . . .
H15 H 1.0904 0.8346 0.4008 0.089 Uiso 1 1 calc R . .
C16 C 0.91807(19) 0.83581(16) 0.3011(2) 0.0659(5) Uani 1 1 d . . .
H16 H 0.9373 0.8147 0.2138 0.079 Uiso 1 1 calc R . .
Cl1 Cl 1.09188(6) 0.89244(6) 0.68104(8) 0.1003(3) Uani 1 1 d . . .
N1 N 0.63717(13) 0.94090(10) 0.12921(16) 0.0502(4) Uani 1 1 d . . .
N2 N 0.48644(15) 1.12481(11) 0.22672(19) 0.0596(4) Uani 1 1 d . . .
H2A H 0.4773 1.1807 0.2191 0.071 Uiso 1 1 calc R . .
N3 N 0.41926(15) 1.07376(12) 0.30281(19) 0.0624(4) Uani 1 1 d . . .
N4 N 0.3555(2) 0.87094(17) 0.4198(3) 0.0995(7) Uani 1 1 d . . .
O1 O 0.72985(15) 0.80146(10) 0.06330(17) 0.0772(5) Uani 1 1 d . . .
O2 O 0.57471(13) 0.80599(9) 0.2363(2) 0.0743(5) Uani 1 1 d . . .
S1 S 0.68046(4) 0.84112(3) 0.18061(5) 0.05503(17) 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 0.0181 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'
Cl Cl 0.3639 0.7018 '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'
S S 0.3331 0.5567 '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
_geom_angle_publ_flag
C2 C1 C6 121.38(18) . . ?
C2 C1 N1 129.07(17) . . ?
C6 C1 N1 109.53(16) . . ?
C3 C2 C1 117.4(2) . . ?
C2 C3 C4 121.8(2) . . ?
C5 C4 C3 121.4(2) . . ?
C4 C5 C6 118.3(2) . . ?
C5 C6 C1 119.77(18) . . ?
C5 C6 C7 135.18(18) . . ?
C1 C6 C7 105.05(16) . . ?
N2 C7 C9 106.51(17) . . ?
N2 C7 C6 143.27(18) . . ?
C9 C7 C6 110.22(16) . . ?
N3 C8 C9 109.31(17) . . ?
N3 C8 C10 117.70(19) . . ?
C9 C8 C10 132.98(19) . . ?
C7 C9 C8 105.93(16) . . ?
C7 C9 N1 108.69(16) . . ?
C8 C9 N1 145.29(17) . . ?
N4 C10 C8 177.1(3) . . ?
C12 C11 C16 121.06(18) . . ?
C12 C11 S1 118.69(14) . . ?
C16 C11 S1 120.26(16) . . ?
C13 C12 C11 119.47(19) . . ?
C12 C13 C14 119.2(2) . . ?
C15 C14 C13 121.84(19) . . ?
C15 C14 Cl1 119.19(17) . . ?
C13 C14 Cl1 118.95(18) . . ?
C14 C15 C16 119.0(2) . . ?
C15 C16 C11 119.5(2) . . ?
C9 N1 C1 106.38(14) . . ?
C9 N1 S1 123.66(13) . . ?
C1 N1 S1 125.13(12) . . ?
N3 N2 C7 112.19(16) . . ?
N2 N3 C8 106.06(16) . . ?
O1 S1 O2 121.44(10) . . ?
O1 S1 N1 106.59(9) . . ?
O2 S1 N1 103.64(8) . . ?
O1 S1 C11 109.26(9) . . ?
O2 S1 C11 109.09(10) . . ?
N1 S1 C11 105.59(8) . . ?
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 C2 1.389(3) . ?
C1 C6 1.408(3) . ?
C1 N1 1.431(2) . ?
C2 C3 1.375(3) . ?
C3 C4 1.385(4) . ?
C4 C5 1.373(3) . ?
C5 C6 1.394(3) . ?
C6 C7 1.436(3) . ?
C7 N2 1.347(2) . ?
C7 C9 1.370(3) . ?
C8 N3 1.343(3) . ?
C8 C9 1.405(3) . ?
C8 C10 1.427(3) . ?
C9 N1 1.412(2) . ?
C10 N4 1.137(3) . ?
C11 C12 1.378(3) . ?
C11 C16 1.382(3) . ?
C11 S1 1.7507(18) . ?
C12 C13 1.369(3) . ?
C13 C14 1.376(3) . ?
C14 C15 1.373(3) . ?
C14 Cl1 1.735(2) . ?
C15 C16 1.374(3) . ?
N1 S1 1.6505(15) . ?
N2 N3 1.334(2) . ?
O1 S1 1.4196(16) . ?
O2 S1 1.4278(16) . ?
