#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:49:17 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178446 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/67/4026717.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_4026717
loop_
_publ_author_name
'Tryfon Zarganes-Tzitzikas'
'Michael A. Terzidis'
'Julia Stephanidou-Stephanatou'
'Constantinos A. Tsoleridis'
'George E. Kostakis'
_publ_contact_author_email       ioulia@chem.auth.gr
_publ_contact_author_name        'Julia Stephanidou-Stephanatou'
_publ_section_title
;
 One-Pot Synthesis of Functionalized Spirobenzofuranones via MCR involving
 3-Cyanochromones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9008
_journal_page_last               9014
_journal_paper_doi               10.1021/jo201732g
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C21 H18 Cl2 N2 O6'
_chemical_formula_weight         465.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                72.405(11)
_cell_angle_beta                 81.083(12)
_cell_angle_gamma                69.498(11)
_cell_formula_units_Z            2
_cell_length_a                   8.8907(13)
_cell_length_b                   9.4940(14)
_cell_length_c                   14.442(2)
_cell_measurement_reflns_used    9408
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      1.48
_cell_volume                     1086.7(3)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector                 'image plate ( 34 cm diameter )'
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8081
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.72
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_T_max  0.9604
_exptl_absorpt_correction_T_min  0.9353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'XPREP in SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4577
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0364
_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)+(0.0503P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0904
_reflns_number_gt                3262
_reflns_number_total             4577
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201732g_si_001.cif
_cod_data_source_block           452m
_cod_database_code               4026717
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cl1 Cl 0.89322(6) 1.08809(6) 0.16154(4) 0.05325(14) Uani 1 1 d .
Cl2 Cl 0.62110(7) 1.07250(7) -0.14229(4) 0.06809(19) Uani 1 1 d .
O1 O 0.97538(14) 0.73421(13) 0.21017(8) 0.0377(3) Uani 1 1 d .
O2 O 0.92978(15) 0.45506(15) 0.10839(9) 0.0448(3) Uani 1 1 d .
O3 O 1.27096(16) 0.55929(17) 0.08590(9) 0.0543(4) Uani 1 1 d .
O4 O 1.42785(14) 0.45378(15) 0.21333(8) 0.0436(3) Uani 1 1 d .
O5 O 1.30940(17) 0.15519(17) 0.44893(9) 0.0580(4) Uani 1 1 d .
O6 O 1.39624(14) 0.15535(14) 0.29476(9) 0.0440(3) Uani 1 1 d .
N2 N 0.97016(18) 0.27516(17) 0.45327(10) 0.0386(3) Uani 1 1 d D
H2N H 1.060(2) 0.208(2) 0.4803(13) 0.046 Uiso 1 1 d D
N1 N 0.59403(19) 0.6656(2) 0.32014(12) 0.0506(4) Uani 1 1 d .
C1 C 0.8467(2) 0.9833(2) 0.09747(13) 0.0417(4) Uani 1 1 d .
C2 C 0.7619(2) 1.0571(2) 0.01368(13) 0.0488(5) Uani 1 1 d .
H2A H 0.7269 1.1678 -0.0087 0.059 Uiso 1 1 calc R
C3 C 0.7275(2) 0.9707(2) -0.03805(13) 0.0498(5) Uani 1 1 d .
C4 C 0.7773(2) 0.8093(2) -0.00945(12) 0.0459(4) Uani 1 1 d .
H4A H 0.7551 0.7510 -0.0456 0.055 Uiso 1 1 calc R
C5 C 0.8618(2) 0.7365(2) 0.07503(12) 0.0389(4) Uani 1 1 d .
C6 C 0.8946(2) 0.8216(2) 0.12781(11) 0.0371(4) Uani 1 1 d .
C7 C 0.92774(19) 0.5714(2) 0.12725(12) 0.0362(4) Uani 1 1 d .
C8 C 0.9899(2) 0.57245(19) 0.22241(11) 0.0353(4) Uani 1 1 d .
C9 C 0.89413(19) 0.5110(2) 0.31111(11) 0.0358(4) Uani 1 1 d .
C10 C 0.7280(2) 0.5922(2) 0.31989(12) 0.0389(4) Uani 1 1 d .
C11 C 0.9930(2) 0.37654(19) 0.36936(11) 0.0345(4) Uani 1 1 d .
C12 C 0.8223(2) 0.2775(2) 0.51724(12) 0.0403(4) Uani 1 1 d .
C13 C 0.8746(3) 0.1347(2) 0.60440(13) 0.0538(5) Uani 1 1 d .
H13A H 0.9557 0.1456 0.6382 0.081 Uiso 1 1 calc R
H13B H 0.9205 0.0402 0.5816 0.081 Uiso 1 1 calc R
H13C H 0.7812 0.1270 0.6491 0.081 Uiso 1 1 calc R
C14 C 0.6972(2) 0.2599(2) 0.46429(14) 0.0490(5) Uani 1 1 d .
H14A H 0.6644 0.3508 0.4081 0.074 Uiso 1 1 calc R
H14B H 0.6032 0.2528 0.5086 0.074 Uiso 1 1 calc R
H14C H 0.7434 0.1650 0.4420 0.074 Uiso 1 1 calc R
C15 C 0.7610(3) 0.4245(2) 0.55294(14) 0.0501(5) Uani 1 1 d .
H15A H 0.7284 0.5165 0.4975 0.075 Uiso 1 1 calc R
H15B H 0.8467 0.4310 0.5851 0.075 Uiso 1 1 calc R
H15C H 0.6685 0.4204 0.5992 0.075 Uiso 1 1 calc R
C16 C 1.15801(19) 0.34837(19) 0.32102(11) 0.0346(4) Uani 1 1 d .
C17 C 1.2959(2) 0.2102(2) 0.36278(12) 0.0386(4) Uani 1 1 d .
C18 C 1.5397(2) 0.0256(2) 0.32876(16) 0.0544(5) Uani 1 1 d .
H18A H 1.6053 -0.0063 0.2729 0.082 Uiso 1 1 calc R
H18B H 1.5084 -0.0624 0.3723 0.082 Uiso 1 1 calc R
H18C H 1.6020 0.0579 0.3640 0.082 Uiso 1 1 calc R
C19 C 1.15850(19) 0.4653(2) 0.24076(11) 0.0347(4) Uani 1 1 d .
C20 C 1.2916(2) 0.4965(2) 0.17091(12) 0.0372(4) Uani 1 1 d .
C21 C 1.5656(2) 0.4749(3) 0.14929(15) 0.0524(5) Uani 1 1 d .
H21A H 1.6600 0.4395 0.1878 0.079 Uiso 1 1 calc R
H21B H 1.5431 0.5856 0.1148 0.079 Uiso 1 1 calc R
H21C H 1.5867 0.4138 0.1020 0.079 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'
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 O1 C8 107.57(12)
C20 O4 C21 116.00(14)
C17 O6 C18 116.01(14)
C11 N2 C12 129.79(15)
C2 C1 C6 117.70(17)
C2 C1 Cl1 121.43(15)
C6 C1 Cl1 120.87(14)
C1 C2 C3 120.74(17)
C4 C3 C2 122.02(17)
C4 C3 Cl2 120.24(17)
C2 C3 Cl2 117.73(15)
C3 C4 C5 116.71(19)
C6 C5 C4 121.71(17)
C6 C5 C7 106.81(14)
C4 C5 C7 131.47(17)
O1 C6 C5 115.05(15)
O1 C6 C1 123.83(16)
C5 C6 C1 121.11(15)
O2 C7 C5 130.68(16)
O2 C7 C8 124.46(15)
C5 C7 C8 104.74(14)
O1 C8 C19 112.11(14)
O1 C8 C9 112.05(13)
C19 C8 C9 103.44(13)
O1 C8 C7 105.15(12)
C19 C8 C7 112.89(13)
C9 C8 C7 111.41(14)
C11 C9 C10 132.08(15)
C11 C9 C8 109.60(14)
C10 C9 C8 118.30(14)
N1 C10 C9 174.83(19)
N2 C11 C9 134.35(16)
N2 C11 C16 118.65(15)
C9 C11 C16 107.00(14)
N2 C12 C14 109.81(14)
N2 C12 C15 110.35(15)
C14 C12 C15 112.94(16)
N2 C12 C13 105.03(14)
C14 C12 C13 109.44(16)
C15 C12 C13 108.96(15)
C19 C16 C17 128.17(15)
C19 C16 C11 109.96(14)
C17 C16 C11 121.84(14)
O5 C17 O6 125.19(16)
O5 C17 C16 122.58(16)
O6 C17 C16 112.21(14)
C16 C19 C20 131.10(15)
C16 C19 C8 109.55(14)
C20 C19 C8 119.29(14)
O3 C20 O4 125.62(16)
O3 C20 C19 121.68(15)
O4 C20 C19 112.65(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.727(2)
Cl2 C3 1.7367(19)
O1 C6 1.3672(19)
O1 C8 1.453(2)
O2 C7 1.208(2)
O3 C20 1.203(2)
O4 C20 1.320(2)
O4 C21 1.450(2)
O5 C17 1.202(2)
O6 C17 1.321(2)
O6 C18 1.454(2)
N2 C11 1.338(2)
N2 C12 1.483(2)
N1 C10 1.150(2)
C1 C2 1.387(3)
C1 C6 1.387(2)
C2 C3 1.393(3)
C3 C4 1.383(3)
C4 C5 1.393(2)
C5 C6 1.387(3)
C5 C7 1.466(2)
C7 C8 1.563(2)
C8 C19 1.498(2)
C8 C9 1.505(2)
C9 C11 1.380(2)
C9 C10 1.412(2)
C11 C16 1.494(2)
C12 C14 1.523(3)
C12 C15 1.525(3)
C12 C13 1.532(3)
C16 C19 1.341(2)
C16 C17 1.487(2)
C19 C20 1.484(2)
