#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/57/4025718.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_4025718
loop_
_publ_author_name
'Huan-Rui Pan'
'Yong-Jia Li'
'Cai-Xia Yan'
'Juan Xing'
'Ying Cheng'
_publ_section_title
;
 Multicomponent Reaction of Imidazo[1,5-a]pyridine Carbenes with Aldehydes
 and Dimethyl Acetylenedicarboxylate or Allenoates: A Straightforward
 Approach to Fully Substituted Furans
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6644
_journal_page_last               6652
_journal_paper_doi               10.1021/jo1014933
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C32 H27 Cl N2 O3'
_chemical_formula_weight         523.01
_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                75.6810(10)
_cell_angle_beta                 78.9090(10)
_cell_angle_gamma                84.9410(10)
_cell_formula_units_Z            2
_cell_length_a                   8.3127(3)
_cell_length_b                   11.2189(4)
_cell_length_c                   15.1578(6)
_cell_measurement_reflns_used    6438
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      2.60
_cell_volume                     1342.88(9)
_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  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11759
_diffrn_reflns_theta_full        27.62
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.9484
_exptl_absorpt_correction_T_min  0.9287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0080(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         6189
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0464
_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)+(0.0571P)²+0.3145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                5016
_reflns_number_total             6189
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1014933_si_002.cif
_cod_data_source_block           080816a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025718
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.67419(17) 0.43376(13) 0.77286(9) 0.0438(3) Uani 1 1 d . . .
C2 C 0.57789(19) 0.34806(16) 0.75710(11) 0.0567(4) Uani 1 1 d . . .
H2 H 0.6103 0.2650 0.7700 0.068 Uiso 1 1 calc R . .
C3 C 0.4350(2) 0.3854(2) 0.72256(13) 0.0745(5) Uani 1 1 d . . .
H3 H 0.3724 0.3270 0.7124 0.089 Uiso 1 1 calc R . .
C4 C 0.3835(2) 0.5072(2) 0.70299(13) 0.0799(6) Uani 1 1 d . . .
H4 H 0.2871 0.5314 0.6796 0.096 Uiso 1 1 calc R . .
C5 C 0.4765(2) 0.5927(2) 0.71841(13) 0.0735(5) Uani 1 1 d . . .
H5 H 0.4423 0.6754 0.7053 0.088 Uiso 1 1 calc R . .
C6 C 0.6208(2) 0.55781(15) 0.75329(11) 0.0565(4) Uani 1 1 d . . .
H6 H 0.6820 0.6169 0.7636 0.068 Uiso 1 1 calc R . .
C7 C 0.93164(18) 0.48751(13) 0.80876(10) 0.0482(3) Uani 1 1 d . . .
H7A H 0.9430 0.5467 0.7494 0.058 Uiso 1 1 calc R . .
H7B H 1.0384 0.4469 0.8143 0.058 Uiso 1 1 calc R . .
C8 C 0.88273(19) 0.55708(13) 0.88471(10) 0.0490(3) Uani 1 1 d . . .
C9 C 0.9714(2) 0.65730(18) 0.87991(16) 0.0744(5) Uani 1 1 d . . .
H9 H 1.0551 0.6835 0.8301 0.089 Uiso 1 1 calc R . .
C10 C 0.9336(3) 0.7179(2) 0.9505(2) 0.0907(7) Uani 1 1 d . . .
H10 H 0.9929 0.7849 0.9494 0.109 Uiso 1 1 calc R . .
C11 C 0.8091(3) 0.6789(2) 1.02160(15) 0.0854(7) Uani 1 1 d . . .
H11 H 0.7815 0.7189 1.0697 0.102 Uiso 1 1 calc R . .
C12 C 0.7255(3) 0.58005(18) 1.02109(14) 0.0834(6) Uani 1 1 d . . .
H12 H 0.6401 0.5538 1.0699 0.100 Uiso 1 1 calc R . .
C13 C 0.88772(16) 0.27667(12) 0.80542(9) 0.0401(3) Uani 1 1 d . . .
C14 C 0.85598(17) 0.17113(12) 0.87170(9) 0.0433(3) Uani 1 1 d . . .
C15 C 0.74899(17) 0.13826(13) 0.96185(9) 0.0452(3) Uani 1 1 d . . .
C16 C 0.6579(2) 0.22696(16) 1.00085(12) 0.0685(5) Uani 1 1 d . . .
H16 H 0.6651 0.3094 0.9698 0.082 Uiso 1 1 calc R . .
C17 C 0.5557(3) 0.19445(18) 1.08589(13) 0.0741(5) Uani 1 1 d . . .
H17 H 0.4946 0.2549 1.1117 0.089 Uiso 1 1 calc R . .
C18 C 0.5450(2) 0.07365(18) 1.13173(11) 0.0640(4) Uani 1 1 d . . .
C19 C 0.6341(3) -0.01526(19) 1.09504(15) 0.0863(6) Uani 1 1 d . . .
H19 H 0.6266 -0.0975 1.1268 0.104 Uiso 1 1 calc R . .
C20 C 0.7359(3) 0.01702(16) 1.01026(13) 0.0752(5) Uani 1 1 d . . .
H20 H 0.7969 -0.0442 0.9853 0.090 Uiso 1 1 calc R . .
C21 C 1.00361(16) 0.24320(12) 0.73008(9) 0.0428(3) Uani 1 1 d . . .
C22 C 1.06640(17) 0.32819(13) 0.64206(9) 0.0454(3) Uani 1 1 d . . .
C23 C 1.2603(2) 0.3550(2) 0.50303(12) 0.0752(5) Uani 1 1 d . . .
H23A H 1.1747 0.3951 0.4705 0.113 Uiso 1 1 calc R . .
H23B H 1.3305 0.3058 0.4665 0.113 Uiso 1 1 calc R . .
H23C H 1.3233 0.4158 0.5141 0.113 Uiso 1 1 calc R . .
C24 C 1.03408(17) 0.11958(13) 0.75609(9) 0.0455(3) Uani 1 1 d . . .
C25 C 1.12769(19) 0.02557(14) 0.70960(11) 0.0522(3) Uani 1 1 d . . .
H25A H 1.1462 -0.0489 0.7557 0.063 Uiso 1 1 calc R . .
H25B H 1.2337 0.0564 0.6772 0.063 Uiso 1 1 calc R . .
C26 C 1.0336(2) -0.00417(18) 0.64102(13) 0.0647(4) Uani 1 1 d . . .
H26A H 0.9316 -0.0409 0.6749 0.078 Uiso 1 1 calc R . .
H26B H 1.0060 0.0721 0.5991 0.078 Uiso 1 1 calc R . .
C27 C 1.12666(19) -0.09032(14) 0.58498(10) 0.0500(3) Uani 1 1 d . . .
C28 C 1.0675(2) -0.20423(15) 0.59117(12) 0.0610(4) Uani 1 1 d . . .
H28 H 0.9718 -0.2292 0.6325 0.073 Uiso 1 1 calc R . .
C29 C 1.1479(3) -0.28146(16) 0.53704(15) 0.0740(5) Uani 1 1 d . . .
H29 H 1.1053 -0.3571 0.5416 0.089 Uiso 1 1 calc R . .
C30 C 1.2887(3) -0.2473(2) 0.47725(14) 0.0787(6) Uani 1 1 d . . .
H30 H 1.3431 -0.2996 0.4411 0.094 Uiso 1 1 calc R . .
C31 C 1.3504(2) -0.1359(2) 0.47032(13) 0.0795(6) Uani 1 1 d . . .
H31 H 1.4474 -0.1127 0.4296 0.095 Uiso 1 1 calc R . .
C32 C 1.2695(2) -0.05702(18) 0.52355(13) 0.0667(4) Uani 1 1 d . . .
H32 H 1.3122 0.0190 0.5177 0.080 Uiso 1 1 calc R . .
Cl1 Cl 0.41545(8) 0.03199(7) 1.23805(4) 0.1042(2) Uani 1 1 d . . .
N1 N 0.81804(14) 0.39577(10) 0.80905(8) 0.0416(3) Uani 1 1 d . . .
N2 N 0.7606(2) 0.51831(13) 0.95312(10) 0.0687(4) Uani 1 1 d . . .
O1 O 0.94492(12) 0.07444(8) 0.84149(7) 0.0480(2) Uani 1 1 d . . .
O2 O 1.18866(14) 0.27707(11) 0.59025(7) 0.0604(3) Uani 1 1 d . . .
O3 O 1.01572(16) 0.43241(10) 0.61876(8) 0.0651(3) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 120.62(13) . . ?
C2 C1 C6 118.05(14) . . ?
N1 C1 C6 121.32(14) . . ?
C3 C2 C1 120.58(17) . . ?
C4 C3 C2 121.21(19) . . ?
C3 C4 C5 118.99(17) . . ?
C4 C5 C6 121.09(18) . . ?
C5 C6 C1 120.09(17) . . ?
N1 C7 C8 115.27(12) . . ?
N2 C8 C9 122.75(15) . . ?
N2 C8 C7 119.33(13) . . ?
C9 C8 C7 117.90(15) . . ?
C8 C9 C10 118.6(2) . . ?
C11 C10 C9 119.4(2) . . ?
C10 C11 C12 118.68(18) . . ?
N2 C12 C11 123.2(2) . . ?
C14 C13 N1 126.40(12) . . ?
C14 C13 C21 106.64(11) . . ?
N1 C13 C21 126.95(12) . . ?
C13 C14 O1 108.91(11) . . ?
C13 C14 C15 135.37(12) . . ?
O1 C14 C15 115.68(12) . . ?
C16 C15 C20 118.04(15) . . ?
C16 C15 C14 121.20(13) . . ?
C20 C15 C14 120.77(14) . . ?
C15 C16 C17 120.61(16) . . ?
C18 C17 C16 119.86(17) . . ?
C19 C18 C17 120.64(16) . . ?
C19 C18 Cl1 119.24(15) . . ?
C17 C18 Cl1 120.12(15) . . ?
C18 C19 C20 119.56(17) . . ?
C15 C20 C19 121.29(17) . . ?
C24 C21 C13 106.54(12) . . ?
C24 C21 C22 128.20(12) . . ?
C13 C21 C22 125.20(12) . . ?
O3 C22 O2 123.17(13) . . ?
O3 C22 C21 124.21(13) . . ?
O2 C22 C21 112.61(12) . . ?
C21 C24 O1 109.49(11) . . ?
C21 C24 C25 134.68(13) . . ?
O1 C24 C25 115.53(12) . . ?
C24 C25 C26 110.68(12) . . ?
C27 C26 C25 113.94(13) . . ?
C32 C27 C28 117.69(15) . . ?
C32 C27 C26 121.46(15) . . ?
C28 C27 C26 120.80(15) . . ?
C29 C28 C27 121.24(17) . . ?
C30 C29 C28 120.21(18) . . ?
C29 C30 C31 119.73(17) . . ?
C30 C31 C32 120.53(18) . . ?
C27 C32 C31 120.59(17) . . ?
C1 N1 C13 118.34(11) . . ?
C1 N1 C7 119.39(11) . . ?
C13 N1 C7 116.15(11) . . ?
C8 N2 C12 117.33(17) . . ?
C24 O1 C14 108.42(10) . . ?
C22 O2 C23 116.44(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.395(2) . ?
C1 N1 1.3997(18) . ?
C1 C6 1.400(2) . ?
C2 C3 1.380(2) . ?
C3 C4 1.372(3) . ?
C4 C5 1.373(3) . ?
C5 C6 1.389(3) . ?
C7 N1 1.4557(17) . ?
C7 C8 1.5192(19) . ?
C8 N2 1.321(2) . ?
C8 C9 1.378(2) . ?
C9 C10 1.378(3) . ?
C10 C11 1.357(3) . ?
C11 C12 1.362(3) . ?
C12 N2 1.352(2) . ?
C13 C14 1.3585(19) . ?
C13 N1 1.4183(16) . ?
C13 C21 1.4485(17) . ?
C14 O1 1.3810(16) . ?
C14 C15 1.4612(19) . ?
C15 C16 1.378(2) . ?
C15 C20 1.379(2) . ?
C16 C17 1.384(2) . ?
C17 C18 1.363(3) . ?
C18 C19 1.356(3) . ?
C18 Cl1 1.7388(16) . ?
C19 C20 1.380(3) . ?
C21 C24 1.3598(19) . ?
C21 C22 1.4670(19) . ?
C22 O3 1.1981(18) . ?
C22 O2 1.3385(17) . ?
C23 O2 1.443(2) . ?
C24 O1 1.3616(17) . ?
C24 C25 1.4922(19) . ?
C25 C26 1.528(2) . ?
C26 C27 1.509(2) . ?
C27 C32 1.378(2) . ?
C27 C28 1.385(2) . ?
C28 C29 1.382(3) . ?
C29 C30 1.356(3) . ?
C30 C31 1.365(3) . ?
C31 C32 1.388(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659281
