#------------------------------------------------------------------------------
#$Date: 2016-03-26 12:42:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180214 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/00/7110014.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_7110014
loop_
_publ_author_name
'Jian Li'
'Shikuan Su'
'Mengyuan Huang'
'Boyi Song'
'Chunju Li'
'Xueshun Jia'
_publ_section_title
;
 Unexpected isocyanide-based cascade cycloaddition reaction with
 methyleneindolinone
;
_journal_name_full               Chem.Commun.
_journal_page_first              10694
_journal_paper_doi               10.1039/c3cc46237d
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C25 H17 Cl N2 O2'
_chemical_formula_weight         412.86
_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                 105.999(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.341(3)
_cell_length_b                   8.1615(13)
_cell_length_c                   17.193(3)
_cell_measurement_reflns_used    3271
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.33
_cell_measurement_theta_min      2.76
_cell_volume                     2069.3(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10331
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.9575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0457
_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)+(0.0404P)²+0.5959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1106
_reflns_number_gt                2939
_reflns_number_total             3663
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc46237d.txt
_cod_data_source_block           120903c_0m
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7110014
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
C1 C 0.33820(12) 0.7963(3) -0.03214(11) 0.0434(5) Uani 1 1 d .
C2 C 0.35105(14) 0.9639(3) -0.03898(13) 0.0529(5) Uani 1 1 d .
C3 C 0.34697(15) 1.0235(3) -0.11565(15) 0.0634(6) Uani 1 1 d .
H3 H 0.3550 1.1349 -0.1226 0.076 Uiso 1 1 calc R
C4 C 0.33141(16) 0.9213(4) -0.18091(15) 0.0697(7) Uani 1 1 d .
H4 H 0.3286 0.9640 -0.2317 0.084 Uiso 1 1 calc R
C5 C 0.31989(16) 0.7568(4) -0.17237(14) 0.0681(7) Uani 1 1 d .
H5 H 0.3096 0.6889 -0.2174 0.082 Uiso 1 1 calc R
C6 C 0.32326(14) 0.6895(3) -0.09719(13) 0.0532(5) Uani 1 1 d .
C7 C 0.3702(2) 1.0751(3) 0.03309(17) 0.0865(8) Uani 1 1 d .
H7A H 0.4271 1.0457 0.0702 0.130 Uiso 1 1 calc R
H7B H 0.3228 1.0646 0.0593 0.130 Uiso 1 1 calc R
H7C H 0.3729 1.1864 0.0158 0.130 Uiso 1 1 calc R
C8 C 0.31337(19) 0.5083(3) -0.08603(17) 0.0782(8) Uani 1 1 d .
H8A H 0.3661 0.4679 -0.0465 0.117 Uiso 1 1 calc R
H8B H 0.3073 0.4532 -0.1366 0.117 Uiso 1 1 calc R
H8C H 0.2605 0.4882 -0.0679 0.117 Uiso 1 1 calc R
C9 C 0.26600(12) 0.6902(2) 0.07284(11) 0.0426(5) Uani 1 1 d .
C10 C 0.30318(12) 0.6143(2) 0.15434(11) 0.0404(4) Uani 1 1 d .
C11 C 0.39558(12) 0.6220(2) 0.17394(11) 0.0432(5) Uani 1 1 d .
C12 C 0.42295(13) 0.6908(3) 0.10418(12) 0.0491(5) Uani 1 1 d .
C13 C 0.25951(12) 0.5441(2) 0.20867(11) 0.0426(5) Uani 1 1 d .
C14 C 0.40038(13) 0.5066(3) 0.30225(11) 0.0463(5) Uani 1 1 d .
C15 C 0.44912(15) 0.4522(3) 0.37997(12) 0.0588(6) Uani 1 1 d .
H15 H 0.4183 0.4100 0.4151 0.071 Uiso 1 1 calc R
C16 C 0.54095(16) 0.4613(3) 0.40347(13) 0.0680(7) Uani 1 1 d .
H16 H 0.5724 0.4261 0.4550 0.082 Uiso 1 1 calc R
C17 C 0.58940(15) 0.5226(3) 0.35171(14) 0.0671(7) Uani 1 1 d .
H17 H 0.6523 0.5279 0.3693 0.080 Uiso 1 1 calc R
C18 C 0.54520(14) 0.5745(3) 0.27584(13) 0.0585(6) Uani 1 1 d .
H18 H 0.5777 0.6139 0.2414 0.070 Uiso 1 1 calc R
C19 C 0.44943(13) 0.5682(3) 0.24980(11) 0.0452(5) Uani 1 1 d .
C20 C 0.15983(13) 0.5222(3) 0.18944(11) 0.0468(5) Uani 1 1 d .
C21 C 0.11094(14) 0.4318(3) 0.12350(13) 0.0551(6) Uani 1 1 d .
C22 C 0.01792(16) 0.4147(4) 0.10648(16) 0.0744(8) Uani 1 1 d .
H22 H -0.0141 0.3545 0.0618 0.089 Uiso 1 1 calc R
C23 C -0.02652(17) 0.4883(4) 0.1567(2) 0.0869(9) Uani 1 1 d .
H23 H -0.0892 0.4792 0.1453 0.104 Uiso 1 1 calc R
C24 C 0.02065(18) 0.5748(4) 0.22340(19) 0.0823(8) Uani 1 1 d .
H24 H -0.0099 0.6220 0.2576 0.099 Uiso 1 1 calc R
C25 C 0.11297(15) 0.5916(3) 0.23975(14) 0.0618(6) Uani 1 1 d .
H25 H 0.1446 0.6503 0.2851 0.074 Uiso 1 1 calc R
Cl1 Cl 0.16735(5) 0.32788(9) 0.06348(4) 0.0764(2) Uani 1 1 d .
N1 N 0.34241(10) 0.7300(2) 0.04613(9) 0.0459(4) Uani 1 1 d .
N2 N 0.30760(11) 0.4937(2) 0.28117(9) 0.0483(4) Uani 1 1 d .
O1 O 0.49777(9) 0.7078(2) 0.09544(9) 0.0705(5) Uani 1 1 d .
O2 O 0.18934(9) 0.71639(19) 0.03420(8) 0.0537(4) 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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 123.07(19)
C6 C1 N1 118.28(19)
C2 C1 N1 118.63(18)
C3 C2 C1 117.0(2)
C3 C2 C7 121.3(2)
C1 C2 C7 121.7(2)
C4 C3 C2 121.2(2)
C4 C3 H3 119.4
C2 C3 H3 119.4
C3 C4 C5 120.7(2)
C3 C4 H4 119.7
C5 C4 H4 119.7
C4 C5 C6 120.9(2)
C4 C5 H5 119.5
C6 C5 H5 119.5
C1 C6 C5 117.2(2)
C1 C6 C8 121.0(2)
C5 C6 C8 121.8(2)
C2 C7 H7A 109.5
C2 C7 H7B 109.5
H7A C7 H7B 109.5
C2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C6 C8 H8A 109.5
C6 C8 H8B 109.5
H8A C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O2 C9 N1 123.70(17)
O2 C9 C10 130.98(17)
N1 C9 C10 105.32(15)
C11 C10 C13 120.33(17)
C11 C10 C9 108.33(16)
C13 C10 C9 131.33(16)
C10 C11 C19 121.24(17)
C10 C11 C12 108.87(16)
C19 C11 C12 129.89(17)
O1 C12 N1 124.75(19)
O1 C12 C11 129.39(18)
N1 C12 C11 105.82(16)
N2 C13 C10 120.32(17)
N2 C13 C20 116.36(16)
C10 C13 C20 123.31(16)
N2 C14 C15 117.78(18)
N2 C14 C19 123.61(17)
C15 C14 C19 118.60(19)
C16 C15 C14 120.0(2)
C16 C15 H15 120.0
C14 C15 H15 120.0
C15 C16 C17 121.3(2)
C15 C16 H16 119.3
C17 C16 H16 119.3
C18 C17 C16 120.6(2)
C18 C17 H17 119.7
C16 C17 H17 119.7
C17 C18 C19 119.4(2)
C17 C18 H18 120.3
C19 C18 H18 120.3
C11 C19 C18 125.10(19)
C11 C19 C14 114.92(17)
C18 C19 C14 119.97(18)
C21 C20 C25 118.03(19)
C21 C20 C13 122.55(19)
C25 C20 C13 119.41(19)
C22 C21 C20 121.4(2)
C22 C21 Cl1 118.6(2)
C20 C21 Cl1 119.93(16)
C23 C22 C21 118.9(3)
C23 C22 H22 120.5
C21 C22 H22 120.5
C24 C23 C22 120.7(2)
C24 C23 H23 119.6
C22 C23 H23 119.6
C23 C24 C25 120.0(3)
C23 C24 H24 120.0
C25 C24 H24 120.0
C24 C25 C20 120.9(2)
C24 C25 H25 119.5
C20 C25 H25 119.5
C12 N1 C9 111.48(15)
C12 N1 C1 124.03(15)
C9 N1 C1 124.45(15)
C13 N2 C14 119.45(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.387(3)
C1 C2 1.391(3)
C1 N1 1.435(2)
C2 C3 1.390(3)
C2 C7 1.498(3)
C3 C4 1.365(4)
C3 H3 0.9300
C4 C5 1.368(4)
C4 H4 0.9300
C5 C6 1.392(3)
C5 H5 0.9300
C6 C8 1.504(3)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 O2 1.200(2)
C9 N1 1.410(2)
C9 C10 1.494(3)
C10 C11 1.365(2)
C10 C13 1.412(2)
C11 C19 1.408(3)
C11 C12 1.486(3)
C12 O1 1.206(2)
C12 N1 1.395(2)
C13 N2 1.327(2)
C13 C20 1.484(3)
C14 N2 1.373(2)
C14 C15 1.411(3)
C14 C19 1.416(3)
C15 C16 1.356(3)
C15 H15 0.9300
C16 C17 1.400(3)
C16 H16 0.9300
C17 C18 1.361(3)
C17 H17 0.9300
C18 C19 1.414(3)
C18 H18 0.9300
C20 C21 1.387(3)
C20 C25 1.389(3)
C21 C22 1.382(3)
C21 Cl1 1.739(2)
C22 C23 1.377(4)
C22 H22 0.9300
C23 C24 1.371(4)
C23 H23 0.9300
C24 C25 1.373(3)
C24 H24 0.9300
C25 H25 0.9300
