#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:48:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180277 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/63/7116388.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_7116388
loop_
_publ_author_name
'Zhao-Lin He'
'Chun-Jiang Wang'
_publ_section_title
;
 Ag(I)-catalyzed tandem [6+3] annulation/isomerization of isocyanoacetates
 with fulvenes: an expedient approach to synthesize fused dihydropyridines
;
_journal_name_full               Chem.Commun.
_journal_page_first              534
_journal_paper_doi               10.1039/C4cc08382B
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C17 H17 N O3'
_chemical_formula_weight         283.32
_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                   10.2469(9)
_cell_length_b                   10.4606(9)
_cell_length_c                   13.5437(12)
_cell_measurement_temperature    296(2)
_cell_volume                     1451.7(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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9608
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9764
_exptl_absorpt_correction_T_min  0.9738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_coef       0.0178(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0293
_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)+(0.0214P)²+0.2728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0660
_reflns_number_gt                2805
_reflns_number_total             3002
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc08382b2.cif
_cod_data_source_block           130427hzl_0m
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7116388
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
C1 C 0.28977(13) 1.07836(13) 1.01751(11) 0.0399(3) Uani 1 1 d .
C2 C 0.20589(15) 1.04265(14) 1.09266(11) 0.0455(3) Uani 1 1 d .
H2 H 0.2300 1.0553 1.1581 0.055 Uiso 1 1 calc R
C3 C 0.08713(14) 0.98849(14) 1.07088(10) 0.0408(3) Uani 1 1 d .
H3 H 0.0316 0.9654 1.1222 0.049 Uiso 1 1 calc R
C4 C 0.04792(12) 0.96735(11) 0.97394(9) 0.0320(3) Uani 1 1 d .
C5 C 0.13350(14) 1.00222(14) 0.90013(10) 0.0402(3) Uani 1 1 d .
H5 H 0.1102 0.9881 0.8347 0.048 Uiso 1 1 calc R
C6 C 0.25337(14) 1.05773(15) 0.92079(11) 0.0442(3) Uani 1 1 d .
H6 H 0.3090 1.0810 0.8696 0.053 Uiso 1 1 calc R
C7 C 0.48597(17) 1.18574(18) 0.97323(15) 0.0662(5) Uani 1 1 d .
H7A H 0.5202 1.1180 0.9331 0.099 Uiso 1 1 calc R
H7B H 0.5567 1.2311 1.0037 0.099 Uiso 1 1 calc R
H7C H 0.4365 1.2434 0.9327 0.099 Uiso 1 1 calc R
C8 C -0.08486(12) 0.90787(12) 0.95207(9) 0.0310(3) Uani 1 1 d .
H8 H -0.1432 0.9274 1.0074 0.037 Uiso 1 1 calc R
C9 C -0.14712(12) 0.95755(12) 0.85898(10) 0.0335(3) Uani 1 1 d .
C10 C -0.13167(13) 0.88934(13) 0.76768(10) 0.0380(3) Uani 1 1 d .
C11 C -0.05956(14) 0.77963(14) 0.76430(10) 0.0417(3) Uani 1 1 d .
H11 H -0.0356 0.7456 0.7035 0.050 Uiso 1 1 calc R
C12 C -0.07713(13) 0.75966(12) 0.94121(9) 0.0331(3) Uani 1 1 d .
H12 H -0.1662 0.7259 0.9455 0.040 Uiso 1 1 calc R
C13 C -0.18843(14) 0.96625(16) 0.69084(11) 0.0471(4) Uani 1 1 d .
H13 H -0.1919 0.9461 0.6240 0.057 Uiso 1 1 calc R
C14 C -0.23576(14) 1.07337(15) 0.73394(12) 0.0485(4) Uani 1 1 d .
H14 H -0.2795 1.1389 0.7014 0.058 Uiso 1 1 calc R
C15 C -0.20790(13) 1.07013(14) 0.83821(11) 0.0412(3) Uani 1 1 d .
H15 H -0.2280 1.1340 0.8835 0.049 Uiso 1 1 calc R
C16 C 0.00221(13) 0.69796(12) 1.02168(11) 0.0362(3) Uani 1 1 d .
C17 C 0.01987(19) 0.6694(2) 1.19335(11) 0.0641(5) Uani 1 1 d .
H17A H 0.0304 0.5787 1.1868 0.096 Uiso 1 1 calc R
H17B H -0.0274 0.6879 1.2528 0.096 Uiso 1 1 calc R
H17C H 0.1041 0.7094 1.1961 0.096 Uiso 1 1 calc R
N1 N -0.02322(12) 0.72088(11) 0.84688(8) 0.0410(3) Uani 1 1 d .
H1 H 0.0326 0.6595 0.8443 0.049 Uiso 1 1 calc R
O1 O 0.40445(10) 1.13391(11) 1.04687(8) 0.0576(3) Uani 1 1 d .
O2 O 0.10077(12) 0.64020(12) 1.00842(8) 0.0631(3) Uani 1 1 d .
O3 O -0.05141(10) 0.71802(10) 1.10966(7) 0.0446(2) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 C6 125.04(14)
O1 C1 C2 115.71(13)
C6 C1 C2 119.24(13)
C3 C2 C1 120.23(13)
C2 C3 C4 121.60(13)
C5 C4 C3 117.29(12)
C5 C4 C8 122.31(11)
C3 C4 C8 120.39(11)
C4 C5 C6 121.85(13)
C1 C6 C5 119.78(13)
C9 C8 C4 113.57(10)
C9 C8 C12 106.60(10)
C4 C8 C12 112.25(10)
C15 C9 C10 107.59(12)
C15 C9 C8 131.71(13)
C10 C9 C8 120.19(11)
C11 C10 C9 120.39(12)
C11 C10 C13 131.65(14)
C9 C10 C13 107.49(12)
N1 C11 C10 120.78(13)
N1 C12 C16 108.20(11)
N1 C12 C8 112.38(10)
C16 C12 C8 112.67(11)
C14 C13 C10 107.21(14)
C13 C14 C15 109.40(13)
C9 C15 C14 108.26(14)
O2 C16 O3 124.49(13)
O2 C16 C12 124.51(13)
O3 C16 C12 110.99(11)
C11 N1 C12 120.35(11)
C1 O1 C7 117.79(13)
C16 O3 C17 116.11(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.3699(16)
C1 C6 1.379(2)
C1 C2 1.384(2)
C2 C3 1.374(2)
C3 C4 1.3908(18)
C4 C5 1.3788(18)
C4 C8 1.5251(17)
C5 C6 1.387(2)
C7 O1 1.409(2)
C8 C9 1.5056(17)
C8 C12 1.5594(17)
C9 C15 1.3616(19)
C9 C10 1.4363(19)
C10 C11 1.366(2)
C10 C13 1.4382(19)
C11 N1 1.3294(18)
C12 N1 1.4498(17)
C12 C16 1.5052(18)
C13 C14 1.353(2)
C14 C15 1.441(2)
C16 O2 1.1906(16)
C16 O3 1.3287(16)
C17 O3 1.4410(18)
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
O1 C1 C2 C3 178.67(13)
C6 C1 C2 C3 -0.7(2)
C1 C2 C3 C4 0.3(2)
C2 C3 C4 C5 0.4(2)
C2 C3 C4 C8 -179.59(12)
C3 C4 C5 C6 -0.8(2)
C8 C4 C5 C6 179.17(13)
O1 C1 C6 C5 -179.02(14)
C2 C1 C6 C5 0.3(2)
C4 C5 C6 C1 0.5(2)
C5 C4 C8 C9 -33.95(17)
C3 C4 C8 C9 146.05(12)
C5 C4 C8 C12 87.06(15)
C3 C4 C8 C12 -92.94(14)
C4 C8 C9 C15 -75.55(17)
C12 C8 C9 C15 160.32(13)
C4 C8 C9 C10 95.10(14)
C12 C8 C9 C10 -29.03(15)
C15 C9 C10 C11 172.12(13)
C8 C9 C10 C11 -0.57(19)
C15 C9 C10 C13 -0.90(15)
C8 C9 C10 C13 -173.58(11)
C9 C10 C11 N1 12.8(2)
C13 C10 C11 N1 -176.16(15)
C9 C8 C12 N1 48.37(14)
C4 C8 C12 N1 -76.57(14)
C9 C8 C12 C16 170.92(10)
C4 C8 C12 C16 45.98(14)
C11 C10 C13 C14 -172.38(15)
C9 C10 C13 C14 -0.45(16)
C10 C13 C14 C15 1.57(17)
C10 C9 C15 C14 1.83(15)
C8 C9 C15 C14 173.35(13)
C13 C14 C15 C9 -2.18(17)
N1 C12 C16 O2 8.01(19)
C8 C12 C16 O2 -116.86(15)
N1 C12 C16 O3 -172.86(11)
C8 C12 C16 O3 62.28(14)
C10 C11 N1 C12 10.3(2)
C16 C12 N1 C11 -167.70(12)
C8 C12 N1 C11 -42.66(17)
C6 C1 O1 C7 6.8(2)
C2 C1 O1 C7 -172.55(14)
O2 C16 O3 C17 2.5(2)
C12 C16 O3 C17 -176.66(13)
