#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:55:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180323 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/37/7153755.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_7153755
loop_
_publ_author_name
'Zhang, Yu'
'Lu, Yingyan'
'Tang, Weifang'
'Lu, Tao'
'Du, Ding'
_publ_section_title
;
 Cooperative N-heterocyclic carbene (NHC)-Lewis acid-mediated
 regioselective umpolung formal [3 + 2] annulations of alkynyl aldehydes
 with isatins.
;
_journal_issue                   19
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3009
_journal_page_last               3015
_journal_paper_doi               10.1039/c4ob00145a
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_sum            'C18 H13 N O3'
_chemical_formula_weight         291.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9540(18)
_cell_length_b                   9.4550(19)
_cell_length_c                   17.176(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1454.1(5)
_computing_cell_refinement       'CAD4 EXPRESS'
_computing_data_collection       'CAD4 EXPRESS(Enraf-Nonius,1994)'
_computing_data_reduction        'XCAD4(Harms & Wocadlo,1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius cad4'
_diffrn_measurement_method       ω/2θ
_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  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3006
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         2.37
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.4(19)
_refine_ls_extinction_coef       0.102(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0474
_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)+(0.0700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1259
_reflns_number_gt                2015
_reflns_number_total             2668
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00145a2.cif
_cod_data_source_block           x
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7153755
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
N N 0.2340(3) 0.8104(3) 0.08229(14) 0.0450(6) Uani 1 1 d .
O1 O -0.0175(2) 0.7609(2) 0.07536(13) 0.0554(6) Uani 1 1 d .
C1 C 0.1539(3) 0.6061(3) 0.14737(14) 0.0354(6) Uani 1 1 d .
O2 O 0.0771(2) 0.6181(2) 0.22097(10) 0.0444(5) Uani 1 1 d .
C2 C 0.1082(3) 0.7347(3) 0.09702(16) 0.0397(7) Uani 1 1 d .
O3 O -0.0886(3) 0.4913(3) 0.28885(12) 0.0674(7) Uani 1 1 d .
C3 C 0.3593(3) 0.7512(3) 0.11948(18) 0.0443(7) Uani 1 1 d .
C4 C 0.5046(4) 0.7987(4) 0.1198(2) 0.0620(10) Uani 1 1 d .
H4A H 0.5316 0.8814 0.0942 0.074 Uiso 1 1 calc R
C5 C 0.6091(4) 0.7188(5) 0.1597(2) 0.0770(12) Uani 1 1 d .
H5A H 0.7082 0.7482 0.1601 0.092 Uiso 1 1 calc R
C6 C 0.5705(4) 0.5977(5) 0.1987(2) 0.0701(11) Uani 1 1 d .
H6A H 0.6429 0.5472 0.2258 0.084 Uiso 1 1 calc R
C7 C 0.4233(3) 0.5499(4) 0.19798(18) 0.0527(8) Uani 1 1 d .
H7A H 0.3966 0.4673 0.2238 0.063 Uiso 1 1 calc R
C8 C 0.3196(3) 0.6271(3) 0.15854(15) 0.0386(7) Uani 1 1 d .
C9 C 0.1025(3) 0.4666(3) 0.11437(15) 0.0374(6) Uani 1 1 d .
C10 C 0.0112(3) 0.4080(4) 0.16594(15) 0.0515(8) Uani 1 1 d .
H10A H -0.0321 0.3191 0.1606 0.062 Uiso 1 1 calc R
C11 C -0.0118(3) 0.5015(4) 0.23185(16) 0.0485(8) Uani 1 1 d .
C12 C 0.1405(3) 0.4155(3) 0.03619(16) 0.0359(6) Uani 1 1 d .
C13 C 0.2522(3) 0.4759(3) -0.00938(15) 0.0406(7) Uani 1 1 d .
H13A H 0.3106 0.5482 0.0111 0.049 Uiso 1 1 calc R
C14 C 0.2775(3) 0.4303(3) -0.08413(17) 0.0460(7) Uani 1 1 d .
H14A H 0.3517 0.4729 -0.1139 0.055 Uiso 1 1 calc R
C15 C 0.1936(4) 0.3220(3) -0.11543(18) 0.0521(8) Uani 1 1 d .
H15A H 0.2106 0.2914 -0.1661 0.063 Uiso 1 1 calc R
C16 C 0.0855(4) 0.2607(4) -0.0710(2) 0.0639(9) Uani 1 1 d .
H16A H 0.0289 0.1871 -0.0915 0.077 Uiso 1 1 calc R
C17 C 0.0591(4) 0.3064(3) 0.00391(18) 0.0576(9) Uani 1 1 d .
H17A H -0.0151 0.2630 0.0333 0.069 Uiso 1 1 calc R
C18 C 0.2332(5) 0.9425(4) 0.0390(2) 0.0707(11) Uani 1 1 d .
H18A H 0.1347 0.9598 0.0191 0.106 Uiso 1 1 calc R
H18B H 0.3025 0.9363 -0.0035 0.106 Uiso 1 1 calc R
H18C H 0.2619 1.0186 0.0728 0.106 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'
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N C3 111.5(2)
C2 N C18 123.0(3)
C3 N C18 125.3(3)
O2 C1 C9 104.7(2)
O2 C1 C8 110.3(2)
C9 C1 C8 117.6(2)
O2 C1 C2 107.6(2)
C9 C1 C2 113.4(2)
C8 C1 C2 103.2(2)
C11 O2 C1 109.4(2)
O1 C2 N 127.3(3)
O1 C2 C1 125.3(2)
N C2 C1 107.4(2)
C4 C3 C8 120.8(3)
C4 C3 N 128.8(3)
C8 C3 N 110.4(2)
C3 C4 C5 117.6(3)
C3 C4 H4A 121.2
C5 C4 H4A 121.2
C6 C5 C4 121.8(3)
C6 C5 H5A 119.1
C4 C5 H5A 119.1
C5 C6 C7 120.3(3)
C5 C6 H6A 119.8
C7 C6 H6A 119.8
C8 C7 C6 118.4(3)
C8 C7 H7A 120.8
C6 C7 H7A 120.8
C7 C8 C3 121.0(3)
C7 C8 C1 131.6(3)
C3 C8 C1 107.4(2)
C10 C9 C12 128.1(3)
C10 C9 C1 107.6(2)
C12 C9 C1 124.2(2)
C9 C10 C11 110.7(3)
C9 C10 H10A 124.6
C11 C10 H10A 124.6
O3 C11 O2 120.5(3)
O3 C11 C10 132.0(3)
O2 C11 C10 107.5(2)
C17 C12 C13 117.4(3)
C17 C12 C9 119.4(2)
C13 C12 C9 123.1(2)
C14 C13 C12 121.0(3)
C14 C13 H13A 119.5
C12 C13 H13A 119.5
C13 C14 C15 120.5(3)
C13 C14 H14A 119.7
C15 C14 H14A 119.7
C16 C15 C14 119.0(3)
C16 C15 H15A 120.5
C14 C15 H15A 120.5
C15 C16 C17 120.7(3)
C15 C16 H16A 119.6
C17 C16 H16A 119.6
C16 C17 C12 121.3(3)
C16 C17 H17A 119.4
C12 C17 H17A 119.4
N C18 H18A 109.5
N C18 H18B 109.5
H18A C18 H18B 109.5
N C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N C2 1.358(4)
N C3 1.408(4)
N C18 1.454(4)
O1 C2 1.211(3)
C1 O2 1.443(3)
C1 C9 1.508(4)
C1 C8 1.509(4)
C1 C2 1.547(4)
O2 C11 1.373(4)
O3 C11 1.200(3)
C3 C4 1.376(4)
C3 C8 1.398(4)
C4 C5 1.384(6)
C4 H4A 0.9300
C5 C6 1.371(6)
C5 H5A 0.9300
C6 C7 1.393(5)
C6 H6A 0.9300
C7 C8 1.362(4)
C7 H7A 0.9300
C9 C10 1.327(4)
C9 C12 1.467(4)
C10 C11 1.451(4)
C10 H10A 0.9300
C12 C17 1.379(4)
C12 C13 1.392(4)
C13 C14 1.373(4)
C13 H13A 0.9300
C14 C15 1.379(4)
C14 H14A 0.9300
C15 C16 1.363(5)
C15 H15A 0.9300
C16 C17 1.378(4)
C16 H16A 0.9300
C17 H17A 0.9300
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C9 C1 O2 C11 -0.6(3)
C8 C1 O2 C11 -127.9(2)
C2 C1 O2 C11 120.3(2)
C3 N C2 O1 177.7(3)
C18 N C2 O1 2.7(4)
C3 N C2 C1 -2.4(3)
C18 N C2 C1 -177.4(3)
O2 C1 C2 O1 -62.1(3)
C9 C1 C2 O1 53.1(4)
C8 C1 C2 O1 -178.7(3)
O2 C1 C2 N 117.9(2)
C9 C1 C2 N -126.8(2)
C8 C1 C2 N 1.4(3)
C2 N C3 C4 -178.5(3)
C18 N C3 C4 -3.7(5)
C2 N C3 C8 2.5(3)
C18 N C3 C8 177.4(3)
C8 C3 C4 C5 0.3(5)
N C3 C4 C5 -178.5(3)
C3 C4 C5 C6 -0.9(5)
C4 C5 C6 C7 1.1(6)
C5 C6 C7 C8 -0.7(5)
C6 C7 C8 C3 0.2(4)
C6 C7 C8 C1 -179.2(3)
C4 C3 C8 C7 0.0(4)
N C3 C8 C7 179.1(3)
C4 C3 C8 C1 179.5(3)
N C3 C8 C1 -1.5(3)
O2 C1 C8 C7 64.8(4)
C9 C1 C8 C7 -55.0(4)
C2 C1 C8 C7 179.5(3)
O2 C1 C8 C3 -114.6(2)
C9 C1 C8 C3 125.6(3)
C2 C1 C8 C3 0.1(3)
O2 C1 C9 C10 -1.6(3)
C8 C1 C9 C10 121.1(3)
C2 C1 C9 C10 -118.6(3)
O2 C1 C9 C12 173.9(2)
C8 C1 C9 C12 -63.4(3)
C2 C1 C9 C12 56.9(3)
C12 C9 C10 C11 -172.1(3)
C1 C9 C10 C11 3.2(3)
C1 O2 C11 O3 -178.3(3)
C1 O2 C11 C10 2.4(3)
C9 C10 C11 O3 177.2(3)
C9 C10 C11 O2 -3.6(3)
C10 C9 C12 C17 11.2(4)
C1 C9 C12 C17 -163.4(3)
C10 C9 C12 C13 -171.6(3)
C1 C9 C12 C13 13.8(4)
C17 C12 C13 C14 1.5(4)
C9 C12 C13 C14 -175.8(3)
C12 C13 C14 C15 -0.9(4)
C13 C14 C15 C16 -0.1(4)
C14 C15 C16 C17 0.5(5)
C15 C16 C17 C12 0.1(5)
C13 C12 C17 C16 -1.1(4)
C9 C12 C17 C16 176.3(3)
