#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/01/7150138.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_7150138
loop_
_publ_author_name
'Norris, Timothy'
'Colon-Cruz, Roberto'
'Ripin, David H. B.'
_publ_section_title
;
 New hydroxy-pyrazoline intermediates, subtle regio-selectivity and
 relative reaction rate variations observed during acid catalyzed and
 neutral pyrazole cyclization.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1844
_journal_page_last               1849
_journal_paper_doi               10.1039/b500413f
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C16 H13 F2 N3 O2 S'
_chemical_formula_weight         349.35
_chemical_name_systematic
;
?
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.250(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.614(2)
_cell_length_b                   7.4840(10)
_cell_length_c                   20.523(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1620.6(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            1790
_diffrn_reflns_theta_full        49.98
_diffrn_reflns_theta_max         49.98
_diffrn_reflns_theta_min         4.19
_exptl_absorpt_coefficient_mu    2.108
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         1674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0419
_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)+(0.0640P)²+0.4721P] where
P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                1271
_reflns_number_total             1674
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b500413f.txt
_cod_data_source_block           f579
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7150138
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
S1X S 0.53678(10) 0.07320(14) 0.13470(5) 0.0474(4) Uani 1 1 d . . .
C1 C 0.6923(4) -0.4103(5) 0.17403(18) 0.0395(10) Uani 1 1 d . . .
H1B H 0.6923 -0.5017 0.2047 0.080 Uiso 1 1 calc R . .
C2 C 0.6245(4) -0.2552(5) 0.18015(19) 0.0425(11) Uani 1 1 d . . .
H2B H 0.5787 -0.2379 0.2158 0.080 Uiso 1 1 calc R . .
C3 C 0.6259(3) -0.1257(5) 0.13194(18) 0.0341(10) Uani 1 1 d . . .
C4 C 0.6990(4) -0.1522(5) 0.08154(18) 0.0421(11) Uani 1 1 d . . .
H4B H 0.7006 -0.0631 0.0500 0.080 Uiso 1 1 calc R . .
N5 N 0.7679(3) -0.2999(4) 0.07550(15) 0.0409(9) Uani 1 1 d . . .
C6 C 0.7603(3) -0.4249(5) 0.12067(17) 0.0320(9) Uani 1 1 d . . .
N7 N 0.8295(3) -0.5840(4) 0.11201(14) 0.0356(8) Uani 1 1 d . . .
N8 N 0.8810(3) -0.6684(4) 0.16759(15) 0.0419(9) Uani 1 1 d . . .
C9 C 0.9420(4) -0.8066(5) 0.14508(19) 0.0418(10) Uani 1 1 d . . .
C10 C 0.9306(4) -0.8132(5) 0.07702(19) 0.0428(11) Uani 1 1 d . . .
H10B H 0.9655 -0.8980 0.0512 0.080 Uiso 1 1 calc R . .
C11 C 0.8573(3) -0.6688(5) 0.05564(18) 0.0349(10) Uani 1 1 d . . .
C12 C 0.8096(3) -0.6191(5) -0.01192(17) 0.0342(10) Uani 1 1 d . . .
C13 C 0.6855(4) -0.5654(5) -0.0298(2) 0.0461(11) Uani 1 1 d . . .
H13B H 0.6295 -0.5575 0.0019 0.080 Uiso 1 1 calc R . .
C14 C 0.6446(5) -0.5239(6) -0.0938(2) 0.0576(13) Uani 1 1 d . . .
H14B H 0.5614 -0.4876 -0.1052 0.080 Uiso 1 1 calc R . .
C15 C 0.7266(6) -0.5360(6) -0.1409(2) 0.0687(15) Uani 1 1 d . . .
H15B H 0.6991 -0.5063 -0.1841 0.080 Uiso 1 1 calc R . .
C16 C 0.8497(5) -0.5922(6) -0.1244(2) 0.0650(14) Uani 1 1 d . . .
H16B H 0.9044 -0.6036 -0.1566 0.080 Uiso 1 1 calc R . .
C17 C 0.8914(4) -0.6313(5) -0.0603(2) 0.0486(11) Uani 1 1 d . . .
H17B H 0.9750 -0.6663 -0.0491 0.080 Uiso 1 1 calc R . .
C18 C 1.0086(4) -0.9308(6) 0.1940(2) 0.0521(12) Uani 1 1 d . . .
H18B H 1.0149 -0.8788 0.2380 0.080 Uiso 1 1 calc R . .
F19 F 0.9482(3) -1.0893(4) 0.19267(17) 0.1126(13) Uani 1 1 d . . .
F20 F 1.1234(3) -0.9713(5) 0.17728(15) 0.1089(13) Uani 1 1 d . . .
O21 O 0.5449(4) 0.1342(5) 0.20054(16) 0.0854(11) Uani 1 1 d . . .
O22 O 0.5756(3) 0.1905(4) 0.08583(17) 0.0782(11) Uani 1 1 d . . .
C23 C 0.3814(4) 0.0083(7) 0.1108(3) 0.0802(17) Uani 1 1 d . . .
H23A H 0.3266 0.1102 0.1112 0.080 Uiso 1 1 calc R . .
H23B H 0.3564 -0.0803 0.1407 0.080 Uiso 1 1 calc R . .
H23C H 0.3755 -0.0410 0.0674 0.080 Uiso 1 1 calc R . .
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'
F F 0.0727 0.0534 '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
O21 S1X O22 118.6(2) . . ?
O21 S1X C23 108.4(3) . . ?
O22 S1X C23 108.2(2) . . ?
O21 S1X C3 108.90(19) . . ?
O22 S1X C3 107.39(18) . . ?
C23 S1X C3 104.5(2) . . ?
C2 C1 C6 117.5(4) . . ?
C1 C2 C3 118.5(3) . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 S1X 119.6(3) . . ?
C2 C3 S1X 121.2(3) . . ?
N5 C4 C3 123.2(4) . . ?
C6 N5 C4 116.2(3) . . ?
N5 C6 C1 125.2(4) . . ?
N5 C6 N7 115.6(3) . . ?
C1 C6 N7 119.2(3) . . ?
N8 N7 C11 112.7(3) . . ?
N8 N7 C6 116.7(3) . . ?
C11 N7 C6 130.6(3) . . ?
C9 N8 N7 103.6(3) . . ?
N8 C9 C10 112.6(3) . . ?
N8 C9 C18 117.7(4) . . ?
C10 C9 C18 129.7(4) . . ?
C11 C10 C9 106.1(3) . . ?
C10 C11 N7 105.0(3) . . ?
C10 C11 C12 128.6(3) . . ?
N7 C11 C12 126.2(3) . . ?
C13 C12 C17 118.6(4) . . ?
C13 C12 C11 122.8(3) . . ?
C17 C12 C11 118.6(3) . . ?
C14 C13 C12 120.7(4) . . ?
C15 C14 C13 120.0(4) . . ?
C14 C15 C16 120.2(4) . . ?
C17 C16 C15 119.9(4) . . ?
C16 C17 C12 120.6(4) . . ?
F20 C18 F19 103.9(4) . . ?
F20 C18 C9 110.4(4) . . ?
F19 C18 C9 110.3(3) . . ?
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
S1X O21 1.420(3) . ?
S1X O22 1.427(3) . ?
S1X C23 1.737(5) . ?
S1X C3 1.768(4) . ?
C1 C2 1.379(5) . ?
C1 C6 1.380(5) . ?
C2 C3 1.386(5) . ?
C3 C4 1.373(5) . ?
C4 N5 1.339(5) . ?
N5 C6 1.326(5) . ?
C6 N7 1.420(5) . ?
N7 N8 1.365(4) . ?
N7 C11 1.379(4) . ?
N8 C9 1.329(5) . ?
C9 C10 1.390(5) . ?
C9 C18 1.489(6) . ?
C10 C11 1.375(5) . ?
C11 C12 1.471(5) . ?
C12 C13 1.387(5) . ?
C12 C17 1.391(5) . ?
C13 C14 1.374(6) . ?
C14 C15 1.372(6) . ?
C15 C16 1.379(7) . ?
C16 C17 1.372(6) . ?
C18 F20 1.337(5) . ?
C18 F19 1.347(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8143807
