#------------------------------------------------------------------------------
#$Date: 2016-04-04 13:57:20 +0300 (Mon, 04 Apr 2016) $
#$Revision: 181385 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/29/1542995.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_1542995
loop_
_publ_author_name
'Li, Ren-Hao'
'Ding, Cheng-Ke'
'Jiang, Ya-Nan'
'Ding, Zong-Cang'
'An, Xiao-Ming'
'Tang, Hai-Tao'
'Jing, Qi-Wei'
'Zhan, Zhuang-Ping'
_publ_section_title
;
 Synthesis of 5,6-Dihydropyrazolo[5,1-a]isoquinolines through
 Indium(III)-Promoted Halocyclizations of N-Propargylic
 Sulfonylhydrazones.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1666
_journal_page_last               1669
_journal_paper_doi               10.1021/acs.orglett.6b00534
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C24 H17 Br I N2'
_chemical_formula_weight         540.21
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.488(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.496(3)
_cell_length_b                   11.563(3)
_cell_length_c                   13.831(3)
_cell_measurement_reflns_used    5223
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.30
_cell_volume                     1996.6(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(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  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13143
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    3.617
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.357202
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1052
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.613
_refine_diff_density_min         -2.048
_refine_diff_density_rms         0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0829P)²+1.8398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1256
_reflns_number_gt                3557
_reflns_number_total             3884
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b00534_si_003.cif
_cod_data_source_block           li704
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1542995
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C21 C 0.4608(4) 0.5716(4) 0.8903(3) 0.0325(10) Uani 1 1 d .
H21A H 0.4140 0.5261 0.8526 0.039 Uiso 1 1 calc R
C20 C 0.5699(3) 0.5634(4) 0.8782(3) 0.0298(9) Uani 1 1 d .
H20A H 0.5959 0.5134 0.8321 0.036 Uiso 1 1 calc R
C9 C 0.7551(3) 0.6714(3) 0.7479(3) 0.0240(8) Uani 1 1 d .
C1 C 1.0284(4) 0.4373(4) 0.6628(3) 0.0326(10) Uani 1 1 d .
H1A H 1.0772 0.3845 0.6397 0.039 Uiso 1 1 calc R
N2 N 0.9496(3) 0.5524(3) 0.7534(2) 0.0239(7) Uani 1 1 d .
C6 C 0.6590(4) 0.7247(4) 0.5681(3) 0.0337(9) Uani 1 1 d .
H6A H 0.6258 0.7416 0.5083 0.040 Uiso 1 1 calc R
C19 C 0.6398(3) 0.6295(3) 0.9346(3) 0.0236(8) Uani 1 1 d .
C3 C 0.8889(3) 0.5513(3) 0.6711(3) 0.0240(8) Uani 1 1 d .
C23 C 0.4898(3) 0.7109(4) 1.0149(3) 0.0341(9) Uani 1 1 d .
H23A H 0.4632 0.7602 1.0613 0.041 Uiso 1 1 calc R
C24 C 0.5992(3) 0.7028(3) 1.0038(3) 0.0276(8) Uani 1 1 d .
H24A H 0.6459 0.7467 1.0430 0.033 Uiso 1 1 calc R
C5 C 0.7449(3) 0.6493(4) 0.5739(3) 0.0295(8) Uani 1 1 d .
H5A H 0.7694 0.6153 0.5180 0.035 Uiso 1 1 calc R
C7 C 0.6223(3) 0.7751(4) 0.6512(3) 0.0331(9) Uani 1 1 d .
H7A H 0.5650 0.8265 0.6472 0.040 Uiso 1 1 calc R
C10 C 0.8090(3) 0.6375(3) 0.8419(3) 0.0224(7) Uani 1 1 d .
C4 C 0.7945(3) 0.6242(3) 0.6633(3) 0.0238(8) Uani 1 1 d .
C8 C 0.6711(3) 0.7489(3) 0.7402(3) 0.0291(8) Uani 1 1 d .
H8A H 0.6469 0.7839 0.7957 0.035 Uiso 1 1 calc R
C11 C 0.9296(3) 0.6245(3) 0.8372(3) 0.0231(7) Uani 1 1 d .
H11A H 0.9558 0.5831 0.8953 0.028 Uiso 1 1 calc R
N1 N 1.0358(3) 0.4834(3) 0.7497(2) 0.0288(7) Uani 1 1 d .
H1B H 1.0848 0.4719 0.7942 0.035 Uiso 1 1 calc R
C18 C 0.7569(3) 0.6209(3) 0.9234(3) 0.0233(7) Uani 1 1 d .
C2 C 0.9395(3) 0.4766(3) 0.6099(3) 0.0299(9) Uani 1 1 d .
H2A H 0.9183 0.4570 0.5467 0.036 Uiso 1 1 calc R
C13 C 1.0896(3) 0.7477(4) 0.7995(3) 0.0324(10) Uani 1 1 d .
H13A H 1.1207 0.6829 0.7724 0.039 Uiso 1 1 calc R
C17 C 0.9414(3) 0.8391(4) 0.8717(3) 0.0316(9) Uani 1 1 d .
H17A H 0.8720 0.8360 0.8932 0.038 Uiso 1 1 calc R
C12 C 0.9868(3) 0.7401(3) 0.8342(3) 0.0259(8) Uani 1 1 d .
I1 I 0.839773(19) 0.57669(2) 1.055433(17) 0.02650(14) Uani 1 1 d .
C16 C 0.9972(4) 0.9417(4) 0.8775(4) 0.0386(11) Uani 1 1 d .
H16A H 0.9660 1.0073 0.9030 0.046 Uiso 1 1 calc R
C14 C 1.1461(4) 0.8511(4) 0.8048(3) 0.0366(10) Uani 1 1 d .
H14A H 1.2146 0.8559 0.7814 0.044 Uiso 1 1 calc R
C15 C 1.0992(4) 0.9460(4) 0.8451(3) 0.0356(10) Uani 1 1 d .
C22 C 0.4206(3) 0.6456(4) 0.9570(3) 0.0373(10) Uani 1 1 d .
H22A H 0.3470 0.6518 0.9632 0.045 Uiso 1 1 calc R
Br1 Br 1.17761(5) 1.08625(4) 0.85793(5) 0.05488(19) 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 0.0033 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'
Br Br -0.2901 2.4595 '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
C22 C21 C20 121.1(4)
C19 C20 C21 119.8(4)
C8 C9 C4 118.8(3)
C8 C9 C10 123.5(3)
C4 C9 C10 117.7(3)
N1 C1 C2 112.0(4)
C3 N2 N1 112.8(3)
C3 N2 C11 124.8(3)
N1 N2 C11 122.4(3)
C5 C6 C7 120.2(4)
C20 C19 C24 119.1(4)
C20 C19 C18 120.6(4)
C24 C19 C18 120.3(4)
N2 C3 C2 105.6(4)
N2 C3 C4 119.0(4)
C2 C3 C4 135.3(4)
C22 C23 C24 119.7(4)
C23 C24 C19 120.6(4)
C6 C5 C4 119.8(4)
C8 C7 C6 119.8(4)
C18 C10 C9 123.6(3)
C18 C10 C11 122.7(3)
C9 C10 C11 113.6(3)
C5 C4 C9 120.2(4)
C5 C4 C3 121.1(4)
C9 C4 C3 118.7(3)
C9 C8 C7 121.0(4)
N2 C11 C12 112.6(3)
N2 C11 C10 107.2(3)
C12 C11 C10 112.5(3)
C1 N1 N2 104.5(3)
C10 C18 C19 126.6(3)
C10 C18 I1 121.5(3)
C19 C18 I1 111.9(3)
C1 C2 C3 105.1(4)
C14 C13 C12 120.7(4)
C16 C17 C12 121.2(4)
C17 C12 C13 118.3(4)
C17 C12 C11 121.0(4)
C13 C12 C11 120.5(3)
C15 C16 C17 119.2(4)
C15 C14 C13 119.0(4)
C16 C15 C14 121.5(4)
C16 C15 Br1 118.9(4)
C14 C15 Br1 119.6(4)
C21 C22 C23 119.7(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C21 C22 1.370(7)
C21 C20 1.383(6)
C20 C19 1.378(6)
C9 C8 1.381(5)
C9 C4 1.399(5)
C9 C10 1.490(5)
C1 N1 1.314(6)
C1 C2 1.380(6)
N2 C3 1.341(5)
N2 N1 1.343(5)
N2 C11 1.458(5)
C6 C5 1.382(6)
C6 C7 1.384(6)
C19 C24 1.391(6)
C19 C18 1.482(5)
C3 C2 1.382(6)
C3 C4 1.450(5)
C23 C22 1.378(7)
C23 C24 1.386(6)
C5 C4 1.390(5)
C7 C8 1.383(6)
C10 C18 1.340(5)
C10 C11 1.518(5)
C11 C12 1.518(5)
C18 I1 2.122(4)
C13 C14 1.388(6)
C13 C12 1.393(5)
C17 C16 1.377(6)
C17 C12 1.388(6)
C16 C15 1.371(7)
C14 C15 1.374(7)
C15 Br1 1.899(4)
