#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:41:52 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178477 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/98/4029869.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_4029869
loop_
_publ_author_name
'Vijay Kumar, S.'
'Saraiah, B.'
'Parameshwarappa, G.'
'Ila, H.'
'Verma, Girijesh K.'
_publ_section_title
;
 Synthesis of N-Functionalized/NH-Multisubstituted Indoles,
 Thienopyrroles, Pyrroloindoles, and Pyrazolopyrroles via Sequential
 One-Pot Base-Mediated and Copper-Catalyzed Inter- and Intramolecular
 Amination of
 2-[2-Bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitriles.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7961
_journal_page_last               7978
_journal_paper_doi               10.1021/jo501114a
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C19 H10 Cl F N2 O'
_chemical_formula_sum            'C19 H10 Cl F N2 O'
_chemical_formula_weight         336.74
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-25
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.875(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1675(3)
_cell_length_b                   12.4426(3)
_cell_length_c                   12.6642(3)
_cell_measurement_reflns_used    4156
_cell_measurement_temperature    105.00(10)
_cell_measurement_theta_max      27.4600
_cell_measurement_theta_min      3.2720
_cell_volume                     1573.38(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      105.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0419
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -25.00   16.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.2100   37.0000  120.0000 41

  2 omega  -45.00   48.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       24.5538  -57.0000 -150.0000 93

  3 omega    3.00   94.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       24.5538   57.0000    0.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0646811000
_diffrn_orient_matrix_UB_12      0.0201263000
_diffrn_orient_matrix_UB_13      -0.0219224000
_diffrn_orient_matrix_UB_21      0.0105563000
_diffrn_orient_matrix_UB_22      0.0437299000
_diffrn_orient_matrix_UB_23      0.0365689000
_diffrn_orient_matrix_UB_31      0.0274328000
_diffrn_orient_matrix_UB_32      0.0305405000
_diffrn_orient_matrix_UB_33      -0.0378650000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6542
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.615
_diffrn_source                   'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description
;
;
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.5749
_exptl_crystal_size_mid          0.3061
_exptl_crystal_size_min          0.3011
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0387P)²+0.5973P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3196
_reflns_number_total             3594
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo501114a_si_003.cif
_cod_data_source_block           6d
_cod_depositor_comments
'Adding full bibliography for 4029867--4029869.cif.'
_cod_original_cell_volume        1573.39(7)
_cod_database_code               4029869
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'c18 h10 n2 cl1 f1 o1'
_chemical_oxdiff_usercomment     105K
_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.
;
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C10(H10), C2(H2), C6(H6), C7(H7), C18(H18), C20(H20),
 C19(H19), C9(H9)
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Cl1 Cl 0.16661(4) 0.54947(3) 0.56710(3) 0.02794(12) Uani 1 1 d .
C14 C 0.37558(14) 0.39674(11) 0.10361(11) 0.0157(3) Uani 1 1 d .
N1 N 0.50305(13) 0.31152(10) -0.13165(10) 0.0235(3) Uani 1 1 d .
C4 C 0.20344(15) 0.52274(12) 0.44103(11) 0.0192(3) Uani 1 1 d .
O1 O 0.52315(11) 0.24811(9) 0.13158(8) 0.0257(3) Uani 1 1 d .
F1 F 0.00022(11) 0.73504(9) -0.07120(8) 0.0438(3) Uani 1 1 d .
N2 N 0.28552(12) 0.46771(9) 0.13469(10) 0.0176(3) Uani 1 1 d .
C16 C 0.44759(14) 0.35326(11) -0.07192(11) 0.0173(3) Uani 1 1 d .
C3 C 0.26747(16) 0.60151(12) 0.39246(12) 0.0217(3) Uani 1 1 d .
H3 H 0.2906 0.6667 0.4269 0.026 Uiso 1 1 calc R
C5 C 0.16759(15) 0.42476(12) 0.39204(12) 0.0211(3) Uani 1 1 d .
H5 H 0.1265 0.3723 0.4269 0.025 Uiso 1 1 calc R
C10 C 0.23789(15) 0.54452(12) -0.14286(12) 0.0204(3) Uani 1 1 d .
H10 H 0.2733 0.5238 -0.2023 0.024 Uiso 1 1 calc R
C11 C 0.27811(14) 0.49354(11) -0.04341(11) 0.0168(3) Uani 1 1 d .
C13 C 0.37185(14) 0.40928(11) -0.00570(11) 0.0164(3) Uani 1 1 d .
C2 C 0.29667(15) 0.58167(12) 0.29148(12) 0.0215(3) Uani 1 1 d .
H2 H 0.3412 0.6331 0.2581 0.026 Uiso 1 1 calc R
C6 C 0.19421(14) 0.40632(12) 0.28999(12) 0.0190(3) Uani 1 1 d .
H6 H 0.1688 0.3419 0.2548 0.023 Uiso 1 1 calc R
C1 C 0.25900(14) 0.48479(11) 0.24085(11) 0.0172(3) Uani 1 1 d .
C7 C 0.13076(16) 0.60899(13) 0.03975(12) 0.0252(3) Uani 1 1 d .
H7 H 0.0950 0.6307 0.0987 0.030 Uiso 1 1 calc R
C8 C 0.09394(17) 0.65482(13) -0.06009(14) 0.0282(4) Uani 1 1 d .
C15 C 0.46192(14) 0.32820(11) 0.17889(11) 0.0173(3) Uani 1 1 d .
C12 C 0.22583(15) 0.52747(11) 0.04589(11) 0.0184(3) Uani 1 1 d .
C18 C 0.60574(17) 0.19608(13) 0.21331(13) 0.0295(4) Uani 1 1 d .
H18 H 0.6598 0.1379 0.2040 0.035 Uiso 1 1 calc R
C20 C 0.50527(15) 0.32596(12) 0.28740(12) 0.0211(3) Uani 1 1 d .
H20 H 0.4790 0.3717 0.3377 0.025 Uiso 1 1 calc R
C19 C 0.59862(15) 0.23994(13) 0.30865(13) 0.0239(3) Uani 1 1 d .
H19 H 0.6455 0.2184 0.3756 0.029 Uiso 1 1 calc R
C9 C 0.14446(16) 0.62638(13) -0.15081(12) 0.0257(3) Uani 1 1 d .
H9 H 0.1159 0.6618 -0.2158 0.031 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 0.0033 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6 15 -8 0.1769 5.8195 14.5020 -8.2155 0.0956 0.3952 0.9136
-2 15 9 0.1346 -2.1587 14.8856 9.3910 0.2333 0.9716 0.0398
-6 -15 8 0.2092 -5.8126 -14.5143 8.1965 -0.0958 -0.3963 -0.9131
3 -14 -10 0.1590 2.5243 -14.4380 -10.0521 -0.2335 -0.9723 0.0089
-12 3 -7 0.1405 -12.0000 3.0000 -7.0000 0.9900 -0.2515 0.0275
12 -3 7 0.1655 12.0000 -3.0000 7.0000 -0.9900 0.2515 -0.0275
-2 -10 15 0.2331 -2.0000 -10.0000 15.0000 -0.4007 0.0901 -0.9282
-14 -1 -1 0.2073 -14.0000 -1.0000 -1.0000 0.9073 -0.2281 -0.3767
-3 9 -14 0.1978 -3.0000 9.0000 -14.0000 0.6821 -0.1501 0.7227
14 1 0 0.2002 14.0000 1.0000 0.0000 -0.8854 0.1915 0.4146
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 C14 C13 108.52(12)
N2 C14 C15 122.80(12)
C13 C14 C15 128.57(13)
C3 C4 Cl1 118.26(11)
C3 C4 C5 122.04(13)
C5 C4 Cl1 119.69(11)
C18 O1 C15 106.14(12)
C14 N2 C1 127.80(12)
C14 N2 C12 108.87(12)
C12 N2 C1 123.25(12)
N1 C16 C13 175.07(16)
C4 C3 C2 118.94(14)
C4 C5 C6 118.77(13)
C9 C10 C11 118.61(14)
C10 C11 C13 133.81(13)
C10 C11 C12 119.88(13)
C12 C11 C13 106.28(12)
C14 C13 C16 128.11(13)
C14 C13 C11 107.79(12)
C16 C13 C11 124.08(13)
C1 C2 C3 119.52(13)
C5 C6 C1 119.54(13)
C2 C1 N2 118.55(12)
C2 C1 C6 121.16(13)
C6 C1 N2 120.27(13)
C8 C7 C12 114.81(14)
F1 C8 C7 117.46(15)
F1 C8 C9 117.35(14)
C7 C8 C9 125.20(15)
O1 C15 C14 114.19(12)
C20 C15 C14 135.88(13)
C20 C15 O1 109.81(12)
N2 C12 C11 108.52(12)
N2 C12 C7 128.88(13)
C7 C12 C11 122.60(13)
C19 C18 O1 111.08(14)
C15 C20 C19 106.48(13)
C18 C19 C20 106.49(14)
C10 C9 C8 118.89(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.7394(14)
C14 N2 1.3817(18)
C14 C13 1.3865(19)
C14 C15 1.446(2)
N1 C16 1.1493(19)
C4 C3 1.383(2)
C4 C5 1.385(2)
O1 C15 1.3712(17)
O1 C18 1.3667(19)
F1 C8 1.3688(18)
N2 C1 1.4360(18)
N2 C12 1.3886(18)
C16 C13 1.423(2)
C3 C2 1.388(2)
C5 C6 1.389(2)
C10 C11 1.401(2)
C10 C9 1.384(2)
C11 C13 1.437(2)
C11 C12 1.402(2)
C2 C1 1.385(2)
C6 C1 1.389(2)
C7 C8 1.373(2)
C7 C12 1.393(2)
C8 C9 1.390(2)
C15 C20 1.362(2)
C18 C19 1.339(2)
C20 C19 1.422(2)
