#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:43:23 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178478 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/99/4029995.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_4029995
loop_
_publ_author_name
'Zhou, Xiaoli'
'Liu, Meiling'
'Luo, Puying'
'Lai, Yingjun'
'Yang, Tangtao'
'Ding, Qiuping'
_publ_section_title
;
 Synthesis of 2-trifluoromethylpyrazolo[5,1-a]isoquinolines via silver
 triflate-catalyzed or electrophile-mediated one-pot tandem reaction.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              2286
_journal_page_last               2292
_journal_paper_doi               10.3762/bjoc.10.238
_journal_volume                  10
_journal_year                    2014
_chemical_formula_sum            'C18 H13 F3 I N2 O2'
_chemical_formula_weight         473.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 95.239(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.222(8)
_cell_length_b                   13.042(5)
_cell_length_c                   14.091(6)
_cell_measurement_reflns_used    8250
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.32
_cell_volume                     3518(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16599
_diffrn_reflns_theta_full        27.71
_diffrn_reflns_theta_max         27.71
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    1.866
_exptl_absorpt_correction_T_max  0.6843
_exptl_absorpt_correction_T_min  0.6426
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1848
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.834
_refine_diff_density_min         -1.260
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0409
_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)+(0.0521P)²+8.9192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                3446
_reflns_number_total             4086
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-10-238-S3.cif
_cod_data_source_block           140825dqp_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/Beilstein/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 4029994--4029995.cif.
;
_cod_original_cell_volume        3518(3)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4029995
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.015818(18) 0.11102(2) 0.08827(2) 0.08308(15) Uani 1 1 d . . .
N1 N 0.89564(12) 0.38791(16) 0.09666(16) 0.0370(5) Uani 1 1 d . . .
N2 N 0.82763(13) 0.41717(18) 0.08445(17) 0.0414(5) Uani 1 1 d . . .
F1 F 0.74212(14) 0.6016(2) 0.17320(18) 0.0829(7) Uani 1 1 d . . .
C17 C 0.82990(16) 0.5178(2) 0.09619(19) 0.0412(6) Uani 1 1 d . . .
C6 C 1.01500(15) 0.4460(2) 0.12549(18) 0.0436(6) Uani 1 1 d . . .
C4 C 0.89818(16) 0.5565(2) 0.11367(18) 0.0410(6) Uani 1 1 d . C .
C5 C 0.94103(15) 0.4689(2) 0.11257(17) 0.0379(5) Uani 1 1 d . . .
C13 C 0.91456(16) 0.2838(2) 0.09279(18) 0.0410(6) Uani 1 1 d . . .
F3 F 0.70939(12) 0.5096(2) 0.0535(2) 0.0959(9) Uani 1 1 d . . .
C3 C 0.9184(2) 0.6643(2) 0.1309(2) 0.0527(7) Uani 1 1 d . . .
F2 F 0.75846(17) 0.6531(2) 0.0341(2) 0.0981(9) Uani 1 1 d . . .
C12 C 0.98379(18) 0.2637(2) 0.1053(2) 0.0490(7) Uani 1 1 d . . .
C14 C 0.85761(18) 0.2079(2) 0.0715(2) 0.0503(7) Uani 1 1 d . . .
H14 H 0.8493 0.1892 0.0041 0.060 Uiso 1 1 calc R . .
C15 C 0.8469(2) 0.1219(3) 0.1394(3) 0.0694(11) Uani 1 1 d . . .
H15A H 0.8352 0.0550 0.1127 0.083 Uiso 1 1 calc R . .
H15B H 0.8760 0.1208 0.1994 0.083 Uiso 1 1 calc R . .
C18 C 0.76022(19) 0.5712(3) 0.0894(2) 0.0563(8) Uani 1 1 d . . .
C11 C 1.03643(17) 0.3424(3) 0.1230(2) 0.0500(7) Uani 1 1 d . . .
C7 C 1.06616(18) 0.5234(3) 0.1399(2) 0.0591(8) Uani 1 1 d . . .
H7 H 1.0526 0.5918 0.1405 0.071 Uiso 1 1 calc R . .
O2 O 0.8691(2) 0.7160(2) 0.1673(3) 0.0976(11) Uani 1 1 d . B .
C16 C 0.7941(2) 0.2037(3) 0.1251(3) 0.0681(10) Uani 1 1 d . . .
H16A H 0.7907 0.2526 0.1763 0.082 Uiso 1 1 calc R . .
H16B H 0.7499 0.1867 0.0896 0.082 Uiso 1 1 calc R . .
C10 C 1.1084(2) 0.3209(4) 0.1372(3) 0.0703(11) Uani 1 1 d . . .
H10 H 1.1235 0.2532 0.1358 0.084 Uiso 1 1 calc R . .
C8 C 1.1358(2) 0.4986(4) 0.1530(3) 0.0739(12) Uani 1 1 d . . .
H8 H 1.1692 0.5501 0.1621 0.089 Uiso 1 1 calc R . .
C9 C 1.1562(2) 0.3970(5) 0.1528(3) 0.0823(14) Uani 1 1 d . . .
H9 H 1.2034 0.3806 0.1634 0.099 Uiso 1 1 calc R . .
C2 C 0.8786(4) 0.8268(3) 0.1794(4) 0.1067(19) Uani 1 1 d . . .
H2A H 0.9235 0.8473 0.1594 0.128 Uiso 1 1 calc R A 2
H2B H 0.8422 0.8632 0.1408 0.128 Uiso 1 1 calc R A 2
C1 C 0.8751(4) 0.8511(4) 0.2787(5) 0.112(2) Uani 1 1 d . B 2
H1A H 0.8314 0.8276 0.2987 0.168 Uiso 1 1 calc R B 2
H1B H 0.8787 0.9240 0.2875 0.168 Uiso 1 1 calc R B 2
H1C H 0.9128 0.8179 0.3161 0.168 Uiso 1 1 calc R B 2
O1 O 0.97195(19) 0.7032(2) 0.1112(3) 0.0992(11) Uani 1 1 d . C 2
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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 N1 C5 113.2(2)
N2 N1 C13 121.0(2)
C5 N1 C13 125.8(2)
C17 N2 N1 104.0(2)
N2 C17 C4 113.4(3)
N2 C17 C18 115.6(3)
C4 C17 C18 131.0(3)
C7 C6 C11 119.1(3)
C7 C6 C5 122.3(3)
C11 C6 C5 118.6(3)
C17 C4 C5 104.2(2)
C17 C4 C3 126.8(3)
C5 C4 C3 129.1(3)
N1 C5 C4 105.2(2)
N1 C5 C6 117.6(2)
C4 C5 C6 137.2(3)
C12 C13 N1 115.9(3)
C12 C13 C14 126.5(3)
N1 C13 C14 117.5(3)
O1 C3 O2 122.7(3)
O1 C3 C4 125.7(3)
O2 C3 C4 111.6(3)
C13 C12 C11 123.3(3)
C13 C12 I1 117.6(2)
C11 C12 I1 118.9(2)
C13 C14 C16 122.9(3)
C13 C14 C15 120.7(3)
C16 C14 C15 59.0(3)
C13 C14 H14 114.4
C16 C14 H14 114.4
C15 C14 H14 114.4
C16 C15 C14 60.3(2)
C16 C15 H15A 117.7
C14 C15 H15A 117.7
C16 C15 H15B 117.7
C14 C15 H15B 117.7
H15A C15 H15B 114.9
F1 C18 F2 106.9(3)
F1 C18 F3 106.1(3)
F2 C18 F3 106.6(3)
F1 C18 C17 112.8(3)
F2 C18 C17 112.7(3)
F3 C18 C17 111.3(3)
C10 C11 C6 118.1(4)
C10 C11 C12 123.1(3)
C6 C11 C12 118.8(3)
C8 C7 C6 120.6(4)
C8 C7 H7 119.7
C6 C7 H7 119.7
C3 O2 C2 118.0(4)
C15 C16 C14 60.7(3)
C15 C16 H16A 117.7
C14 C16 H16A 117.7
C15 C16 H16B 117.7
C14 C16 H16B 117.7
H16A C16 H16B 114.8
C9 C10 C11 121.4(4)
C9 C10 H10 119.3
C11 C10 H10 119.3
C7 C8 C9 120.0(4)
C7 C8 H8 120.0
C9 C8 H8 120.0
C10 C9 C8 120.9(4)
C10 C9 H9 119.6
C8 C9 H9 119.6
C1 C2 O2 108.3(5)
C1 C2 H2A 110.0
O2 C2 H2A 110.0
C1 C2 H2B 110.0
O2 C2 H2B 110.0
H2A C2 H2B 108.4
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C12 2.104(3)
N1 N2 1.358(3)
N1 C5 1.375(3)
N1 C13 1.408(3)
N2 C17 1.323(4)
F1 C18 1.322(4)
C17 C4 1.406(4)
C17 C18 1.505(4)
C6 C7 1.411(5)
C6 C11 1.415(5)
C6 C5 1.448(4)
C4 C5 1.409(4)
C4 C3 1.473(4)
C13 C12 1.352(4)
C13 C14 1.486(4)
F3 C18 1.329(4)
C3 O1 1.203(5)
C3 O2 1.305(5)
F2 C18 1.321(4)
C12 C11 1.447(5)
C14 C16 1.494(5)
C14 C15 1.501(5)
C14 H14 0.9800
C15 C16 1.475(6)
C15 H15A 0.9700
C15 H15B 0.9700
C11 C10 1.408(5)
C7 C8 1.374(6)
C7 H7 0.9300
O2 C2 1.464(4)
C16 H16A 0.9700
C16 H16B 0.9700
C10 C9 1.357(7)
C10 H10 0.9300
C8 C9 1.381(7)
C8 H8 0.9300
C9 H9 0.9300
C2 C1 1.443(8)
C2 H2A 0.9700
C2 H2B 0.9700
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
