#------------------------------------------------------------------------------
#$Date: 2019-11-17 04:48:16 +0100 (dom 17 de nov de 2019) $
#$Revision: 228213 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/20/7122074.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_7122074
loop_
_publ_author_name
'Su, Shikuan'
'Li, Jianxiong'
'Sun, Mingming'
'Zhao, Hongbin'
'Chen, Yali'
'Li, Jian'
_publ_section_title
;
 A domino reaction of 2-isocyanophenyloxyacrylate and aryne to synthesize
 arenes with vicinal olefin and benzoxazole.
;
_journal_issue                   69
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9611
_journal_page_last               9614
_journal_paper_doi               10.1039/c8cc05735d
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C17 H13 N O3'
_chemical_formula_weight         279.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-07-09 deposited with the CCDC.
2018-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.119(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.914(5)
_cell_length_b                   21.762(10)
_cell_length_c                   5.713(3)
_cell_measurement_reflns_used    1334
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      3.37
_cell_volume                     1356.6(11)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3878
_diffrn_reflns_point_group_measured_fraction_full 0.761
_diffrn_reflns_point_group_measured_fraction_max 0.733
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_min         1.872
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       sheet
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
; 
 Flack x determined using 527 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2306
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0533
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0904P)²+0.2932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1538
_reflns_Friedel_coverage         0.488
_reflns_Friedel_fraction_full    0.525
_reflns_Friedel_fraction_max     0.483
_reflns_number_gt                1912
_reflns_number_total             2306
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc05735d2.cif
_cod_data_source_block           mo_70627b
_cod_depositor_comments
'Adding full bibliography for 7122074--7122075.cif.'
_cod_original_cell_volume        1356.7(11)
_cod_database_code               7122074
_shelx_shelxl_version_number     2014/7
_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. 
;
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_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'
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
_atom_site_refinement_flags_adp
N1 N 0.0798(3) 0.32829(15) 0.1629(6) 0.0212(7) Uani 1 1 d . .
O1 O -0.2419(3) 0.43729(14) -0.0522(6) 0.0332(8) Uani 1 1 d . .
O2 O -0.3133(3) 0.40646(18) -0.4051(6) 0.0418(9) Uani 1 1 d . .
O3 O 0.2817(3) 0.30560(13) 0.1621(5) 0.0241(7) Uani 1 1 d . .
C1 C -0.2273(5) 0.4190(2) -0.2763(7) 0.0295(10) Uani 1 1 d . .
C2 C -0.0990(5) 0.4155(2) -0.3445(9) 0.0310(10) Uani 1 1 d . .
H2 H -0.0818 0.4143 -0.5068 0.037 Uiso 1 1 calc R U
C3 C -0.0059(4) 0.41387(18) -0.1940(8) 0.0256(9) Uani 1 1 d . .
H3 H -0.0230 0.4156 -0.0317 0.031 Uiso 1 1 calc R U
C4 C 0.1244(4) 0.40956(18) -0.2638(8) 0.0247(9) Uani 1 1 d . .
C5 C 0.1620(4) 0.4426(2) -0.4632(8) 0.0270(10) Uani 1 1 d . .
H5 H 0.1030 0.4658 -0.5499 0.032 Uiso 1 1 calc R U
C6 C 0.2816(5) 0.44220(19) -0.5354(8) 0.0322(11) Uani 1 1 d . .
H6 H 0.3044 0.4647 -0.6702 0.039 Uiso 1 1 calc R U
C7 C 0.3677(4) 0.4090(2) -0.4112(8) 0.0308(10) Uani 1 1 d . .
H7 H 0.4505 0.4090 -0.4599 0.037 Uiso 1 1 calc R U
C8 C 0.3352(4) 0.37537(19) -0.2145(8) 0.0267(10) Uani 1 1 d . .
H8 H 0.3956 0.3523 -0.1308 0.032 Uiso 1 1 calc R U
C9 C 0.2123(4) 0.37540(17) -0.1389(7) 0.0201(8) Uani 1 1 d . .
C10 C 0.1836(4) 0.33735(17) 0.0632(6) 0.0200(8) Uani 1 1 d . .
C11 C 0.1071(4) 0.28732(17) 0.3471(7) 0.0211(8) Uani 1 1 d . .
C12 C 0.0338(4) 0.26202(19) 0.5189(8) 0.0274(10) Uani 1 1 d . .
H12 H -0.0512 0.2711 0.5253 0.033 Uiso 1 1 calc R U
C13 C 0.0895(4) 0.2233(2) 0.6792(8) 0.0281(10) Uani 1 1 d . .
H13 H 0.0416 0.2057 0.7991 0.034 Uiso 1 1 calc R U
C14 C 0.2131(4) 0.2094(2) 0.6710(8) 0.0274(10) Uani 1 1 d . .
H14 H 0.2467 0.1817 0.7835 0.033 Uiso 1 1 calc R U
C15 C 0.2911(4) 0.2347(2) 0.5019(8) 0.0286(10) Uani 1 1 d . .
H15 H 0.3764 0.2264 0.4960 0.034 Uiso 1 1 calc R U
C16 C 0.2292(4) 0.27348(18) 0.3437(7) 0.0228(9) Uani 1 1 d . .
C17 C -0.3651(5) 0.4388(2) 0.0284(9) 0.0351(11) Uani 1 1 d . .
H17A H -0.4075 0.4746 -0.0380 0.053 Uiso 1 1 calc R U
H17B H -0.3644 0.4414 0.1996 0.053 Uiso 1 1 calc R U
H17C H -0.4078 0.4012 -0.0213 0.053 Uiso 1 1 calc R U
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
C10 N1 C11 104.6(3)
C1 O1 C17 116.1(4)
C16 O3 C10 103.2(3)
O2 C1 O1 122.5(5)
O2 C1 C2 124.1(4)
O1 C1 C2 113.5(4)
C3 C2 C1 123.9(4)
C2 C3 C4 123.7(4)
C9 C4 C5 118.3(4)
C9 C4 C3 123.1(4)
C5 C4 C3 118.6(4)
C6 C5 C4 122.0(4)
C7 C6 C5 119.5(4)
C6 C7 C8 120.8(4)
C7 C8 C9 120.2(4)
C4 C9 C8 119.3(4)
C4 C9 C10 123.3(4)
C8 C9 C10 117.3(3)
N1 C10 O3 114.9(3)
N1 C10 C9 129.6(3)
O3 C10 C9 115.4(3)
C16 C11 C12 119.8(4)
C16 C11 N1 108.7(3)
C12 C11 N1 131.5(4)
C13 C12 C11 117.4(4)
C12 C13 C14 121.9(4)
C13 C14 C15 122.6(4)
C16 C15 C14 112.8(4)
C11 C16 O3 108.5(3)
C11 C16 C15 125.6(4)
O3 C16 C15 125.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C10 1.293(5)
N1 C11 1.407(6)
O1 C1 1.353(5)
O1 C17 1.430(6)
O2 C1 1.212(6)
O3 C16 1.385(5)
O3 C10 1.386(5)
C1 C2 1.463(7)
C2 C3 1.319(6)
C3 C4 1.487(6)
C4 C9 1.398(6)
C4 C5 1.415(7)
C5 C6 1.377(7)
C6 C7 1.372(7)
C7 C8 1.393(6)
C8 C9 1.418(5)
C9 C10 1.460(6)
C11 C16 1.367(6)
C11 C12 1.391(6)
C12 C13 1.376(7)
C13 C14 1.385(7)
C14 C15 1.412(7)
C15 C16 1.400(6)
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
C17 O1 C1 O2 2.5(6)
C17 O1 C1 C2 -177.1(4)
O2 C1 C2 C3 -162.3(5)
O1 C1 C2 C3 17.3(6)
C1 C2 C3 C4 179.2(4)
C2 C3 C4 C9 -142.9(4)
C2 C3 C4 C5 38.5(6)
C9 C4 C5 C6 -0.4(6)
C3 C4 C5 C6 178.3(4)
C4 C5 C6 C7 -0.1(7)
C5 C6 C7 C8 0.6(7)
C6 C7 C8 C9 -0.5(6)
C5 C4 C9 C8 0.5(6)
C3 C4 C9 C8 -178.2(4)
C5 C4 C9 C10 -177.2(4)
C3 C4 C9 C10 4.1(6)
C7 C8 C9 C4 0.0(6)
C7 C8 C9 C10 177.8(4)
C11 N1 C10 O3 0.4(4)
C11 N1 C10 C9 179.6(4)
C16 O3 C10 N1 0.1(4)
C16 O3 C10 C9 -179.2(3)
C4 C9 C10 N1 -0.6(6)
C8 C9 C10 N1 -178.4(4)
C4 C9 C10 O3 178.6(3)
C8 C9 C10 O3 0.8(5)
C10 N1 C11 C16 -0.8(4)
C10 N1 C11 C12 178.1(4)
C16 C11 C12 C13 -0.3(6)
N1 C11 C12 C13 -179.1(4)
C11 C12 C13 C14 -0.5(6)
C12 C13 C14 C15 1.4(7)
C13 C14 C15 C16 -1.5(6)
C12 C11 C16 O3 -178.2(4)
N1 C11 C16 O3 0.9(4)
C12 C11 C16 C15 0.1(6)
N1 C11 C16 C15 179.2(4)
C10 O3 C16 C11 -0.6(4)
C10 O3 C16 C15 -178.9(4)
C14 C15 C16 C11 0.8(6)
C14 C15 C16 O3 178.8(4)
