#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:09:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178423 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/44/4024406.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_4024406
loop_
_publ_author_name
'Ying Cheng'
'Bo Wang'
'Xiao-Rong Wang'
'Jian-Hong Zhang'
'De-Cai Fang'
_publ_section_title
;
An Experimental and Theoretical Study on the Interaction of N-Heterocyclic
Carbene-Derived 1,3-Dipoles with Methoxycarbonylallenes: Highly Regio- and
Stereoselective [3+2]-Cycloadditions Controlled by the Structures
of N-Heterocycles of 1,3-Dipoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2357
_journal_page_last               2367
_journal_paper_doi               10.1021/jo802687m
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C38 H38 N4 O3 S'
_chemical_formula_weight         630.78
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 109.745(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7265(3)
_cell_length_b                   27.9714(8)
_cell_length_c                   12.3434(4)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.16
_cell_measurement_theta_min      2.28
_cell_volume                     3485.71(18)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            38014
_diffrn_reflns_theta_full        27.60
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         8056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0466
_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)+(0.0455P)²+1.0361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1188
_reflns_number_gt                5811
_reflns_number_total             8056
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802687m_si_005.cif
_cod_data_source_block           080103b_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
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
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4024406
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.92816(16) 0.12235(6) 0.54063(15) 0.0487(4) Uani 1 1 d . . .
C2 C 0.91229(18) 0.07935(7) 0.48235(17) 0.0633(5) Uani 1 1 d . . .
H2 H 0.8493 0.0576 0.4880 0.076 Uiso 1 1 calc R . .
C3 C 0.9892(2) 0.06850(10) 0.4159(2) 0.0830(7) Uani 1 1 d . . .
H3 H 0.9764 0.0398 0.3755 0.100 Uiso 1 1 calc R . .
C4 C 1.0852(2) 0.10017(11) 0.4095(2) 0.0878(8) Uani 1 1 d . . .
H4 H 1.1371 0.0929 0.3648 0.105 Uiso 1 1 calc R . .
C5 C 1.1035(2) 0.14226(9) 0.4690(2) 0.0864(8) Uani 1 1 d . . .
H5 H 1.1690 0.1634 0.4655 0.104 Uiso 1 1 calc R . .
C6 C 1.02498(19) 0.15368(7) 0.5348(2) 0.0708(6) Uani 1 1 d . . .
H6 H 1.0377 0.1824 0.5749 0.085 Uiso 1 1 calc R . .
C7 C 0.78638(14) 0.16873(5) 0.60845(13) 0.0399(3) Uani 1 1 d . . .
C8 C 0.70483(14) 0.17327(5) 0.69017(12) 0.0365(3) Uani 1 1 d . . .
C9 C 0.66032(15) 0.22672(5) 0.68965(13) 0.0377(3) Uani 1 1 d . . .
H9 H 0.7157 0.2412 0.7623 0.045 Uiso 1 1 calc R . .
C10 C 0.51830(16) 0.22890(5) 0.68666(13) 0.0415(4) Uani 1 1 d . . .
C11 C 0.3837(2) 0.21941(9) 0.80255(19) 0.0779(6) Uani 1 1 d . . .
H11A H 0.3374 0.2486 0.7730 0.117 Uiso 1 1 calc R . .
H11B H 0.3924 0.2160 0.8821 0.117 Uiso 1 1 calc R . .
H11C H 0.3349 0.1928 0.7596 0.117 Uiso 1 1 calc R . .
C12 C 0.68536(15) 0.25390(5) 0.59306(13) 0.0405(3) Uani 1 1 d . . .
C13 C 0.66263(17) 0.29987(6) 0.56959(14) 0.0474(4) Uani 1 1 d . . .
H13 H 0.6813 0.3115 0.5062 0.057 Uiso 1 1 calc R . .
C14 C 0.60956(19) 0.33524(6) 0.63512(15) 0.0551(4) Uani 1 1 d . . .
H14 H 0.5826 0.3177 0.6922 0.066 Uiso 1 1 calc R . .
C15 C 0.7183(3) 0.37006(9) 0.6983(3) 0.1074(9) Uani 1 1 d . . .
H15A H 0.7936 0.3526 0.7467 0.161 Uiso 1 1 calc R . .
H15B H 0.6865 0.3911 0.7448 0.161 Uiso 1 1 calc R . .
H15C H 0.7435 0.3885 0.6435 0.161 Uiso 1 1 calc R . .
C16 C 0.4897(3) 0.36177(8) 0.5562(2) 0.0875(7) Uani 1 1 d . . .
H16A H 0.5126 0.3773 0.4962 0.131 Uiso 1 1 calc R . .
H16B H 0.4616 0.3853 0.5998 0.131 Uiso 1 1 calc R . .
H16C H 0.4190 0.3395 0.5228 0.131 Uiso 1 1 calc R . .
C17 C 0.89491(14) 0.17263(6) 0.88252(13) 0.0430(4) Uani 1 1 d . . .
C18 C 0.96924(17) 0.20709(7) 0.84997(17) 0.0557(4) Uani 1 1 d . . .
H18 H 0.9390 0.2197 0.7760 0.067 Uiso 1 1 calc R . .
C19 C 1.0886(2) 0.22242(8) 0.9285(2) 0.0755(6) Uani 1 1 d . . .
H19 H 1.1388 0.2450 0.9061 0.091 Uiso 1 1 calc R . .
C20 C 1.1334(2) 0.20497(10) 1.0383(2) 0.0942(8) Uani 1 1 d . . .
H20 H 1.2134 0.2156 1.0904 0.113 Uiso 1 1 calc R . .
C21 C 1.0592(2) 0.17165(10) 1.07064(19) 0.0888(7) Uani 1 1 d . . .
H21 H 1.0889 0.1601 1.1457 0.107 Uiso 1 1 calc R . .
C22 C 0.94124(17) 0.15482(7) 0.99414(15) 0.0596(5) Uani 1 1 d . . .
H22 H 0.8931 0.1317 1.0172 0.072 Uiso 1 1 calc R . .
C23 C 0.60522(14) 0.11037(5) 0.75223(12) 0.0366(3) Uani 1 1 d . . .
C24 C 0.50593(15) 0.07497(5) 0.75714(13) 0.0401(3) Uani 1 1 d . . .
C25 C 0.54331(18) 0.03829(6) 0.83783(14) 0.0493(4) Uani 1 1 d . . .
H25 H 0.6305 0.0362 0.8874 0.059 Uiso 1 1 calc R . .
C26 C 0.4507(2) 0.00492(6) 0.84439(16) 0.0596(5) Uani 1 1 d . . .
H26 H 0.4761 -0.0196 0.8983 0.072 Uiso 1 1 calc R . .
C27 C 0.3223(2) 0.00779(8) 0.77200(19) 0.0690(6) Uani 1 1 d . . .
H27 H 0.2608 -0.0149 0.7764 0.083 Uiso 1 1 calc R . .
C28 C 0.28390(19) 0.04411(8) 0.69298(19) 0.0712(6) Uani 1 1 d . . .
H28 H 0.1963 0.0462 0.6446 0.085 Uiso 1 1 calc R . .
C29 C 0.37517(16) 0.07759(7) 0.68518(16) 0.0551(4) Uani 1 1 d . . .
H29 H 0.3486 0.1021 0.6312 0.066 Uiso 1 1 calc R . .
C30 C 0.54075(14) 0.12005(5) 0.54050(12) 0.0388(3) Uani 1 1 d . . .
C31 C 0.46539(17) 0.14859(7) 0.45109(14) 0.0521(4) Uani 1 1 d . . .
H31 H 0.4508 0.1805 0.4642 0.063 Uiso 1 1 calc R . .
C32 C 0.4115(2) 0.12933(8) 0.34139(15) 0.0653(5) Uani 1 1 d . . .
H32 H 0.3612 0.1486 0.2809 0.078 Uiso 1 1 calc R . .
C33 C 0.4316(2) 0.08236(8) 0.32166(16) 0.0686(6) Uani 1 1 d . . .
H33 H 0.3929 0.0695 0.2485 0.082 Uiso 1 1 calc R . .
C34 C 0.5090(2) 0.05420(7) 0.40976(17) 0.0652(5) Uani 1 1 d . . .
H34 H 0.5239 0.0224 0.3958 0.078 Uiso 1 1 calc R . .
C35 C 0.56477(18) 0.07292(6) 0.51931(15) 0.0515(4) Uani 1 1 d . . .
H35 H 0.6183 0.0539 0.5786 0.062 Uiso 1 1 calc R . .
C36 C 0.1448(6) 0.0577(2) 0.9439(6) 0.244(3) Uani 1 1 d . . .
H36A H 0.1111 0.0725 0.9984 0.366 Uiso 1 1 calc R . .
H36B H 0.1465 0.0806 0.8865 0.366 Uiso 1 1 calc R . .
H36C H 0.2329 0.0461 0.9830 0.366 Uiso 1 1 calc R . .
C37 C 0.0588(6) 0.01739(18) 0.8884(4) 0.161(2) Uani 1 1 d . . .
C38 C -0.0704(5) 0.02760(17) 0.8074(4) 0.201(3) Uani 1 1 d . . .
H38A H -0.1148 -0.0018 0.7777 0.302 Uiso 1 1 calc R . .
H38B H -0.0616 0.0463 0.7452 0.302 Uiso 1 1 calc R . .
H38C H -0.1209 0.0451 0.8452 0.302 Uiso 1 1 calc R . .
N1 N 0.85029(13) 0.13052(5) 0.61163(12) 0.0457(3) Uani 1 1 d . . .
N2 N 0.77570(12) 0.15573(5) 0.80602(11) 0.0435(3) Uani 1 1 d . . .
N3 N 0.59209(11) 0.13911(4) 0.65558(10) 0.0361(3) Uani 1 1 d . . .
N4 N 0.70691(12) 0.12015(4) 0.84035(10) 0.0409(3) Uani 1 1 d . . .
O1 O 0.42272(11) 0.23639(5) 0.60333(10) 0.0551(3) Uani 1 1 d . . .
O2 O 0.51375(12) 0.22081(5) 0.79184(10) 0.0561(3) Uani 1 1 d . . .
O3 O 0.0953(3) -0.02371(11) 0.9078(3) 0.1875(14) Uani 1 1 d . . .
S1 S 0.76586(5) 0.218436(16) 0.51747(4) 0.05336(14) 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'
S S 0.1246 0.1234 '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
C6 C1 C2 119.24(17) . . ?
C6 C1 N1 122.72(17) . . ?
C2 C1 N1 117.85(16) . . ?
C3 C2 C1 120.5(2) . . ?
C4 C3 C2 120.0(2) . . ?
C5 C4 C3 119.8(2) . . ?
C4 C5 C6 120.4(2) . . ?
C1 C6 C5 120.0(2) . . ?
N1 C7 C8 117.99(13) . . ?
N1 C7 S1 129.80(12) . . ?
C8 C7 S1 112.09(10) . . ?
N2 C8 N3 99.75(11) . . ?
N2 C8 C7 112.90(12) . . ?
N3 C8 C7 110.14(11) . . ?
N2 C8 C9 112.42(12) . . ?
N3 C8 C9 113.24(11) . . ?
C7 C8 C9 108.28(11) . . ?
C12 C9 C10 113.96(12) . . ?
C12 C9 C8 110.33(12) . . ?
C10 C9 C8 109.95(12) . . ?
O1 C10 O2 124.18(15) . . ?
O1 C10 C9 126.13(14) . . ?
O2 C10 C9 109.68(13) . . ?
C13 C12 C9 126.34(14) . . ?
C13 C12 S1 121.00(12) . . ?
C9 C12 S1 112.42(11) . . ?
C12 C13 C14 126.60(15) . . ?
C13 C14 C16 111.62(15) . . ?
C13 C14 C15 109.48(17) . . ?
C16 C14 C15 110.70(19) . . ?
C22 C17 N2 119.36(15) . . ?
C22 C17 C18 119.07(15) . . ?
N2 C17 C18 121.57(15) . . ?
C19 C18 C17 119.66(19) . . ?
C20 C19 C18 121.0(2) . . ?
C19 C20 C21 119.2(2) . . ?
C20 C21 C22 121.4(2) . . ?
C21 C22 C17 119.6(2) . . ?
N4 C23 N3 114.23(13) . . ?
N4 C23 C24 121.92(13) . . ?
N3 C23 C24 123.63(13) . . ?
C29 C24 C25 118.85(15) . . ?
C29 C24 C23 121.89(14) . . ?
C25 C24 C23 119.25(14) . . ?
C26 C25 C24 119.99(17) . . ?
C27 C26 C25 120.41(18) . . ?
C26 C27 C28 120.12(18) . . ?
C27 C28 C29 120.15(19) . . ?
C28 C29 C24 120.47(17) . . ?
C31 C30 C35 119.70(15) . . ?
C31 C30 N3 119.98(14) . . ?
C35 C30 N3 120.31(14) . . ?
C30 C31 C32 119.59(18) . . ?
C33 C32 C31 120.50(18) . . ?
C32 C33 C34 120.03(17) . . ?
C33 C34 C35 120.25(19) . . ?
C34 C35 C30 119.87(17) . . ?
O3 C37 C38 119.8(6) . . ?
O3 C37 C36 121.6(6) . . ?
C38 C37 C36 118.5(4) . . ?
C7 N1 C1 122.94(14) . . ?
N4 N2 C17 119.87(12) . . ?
N4 N2 C8 112.69(11) . . ?
C17 N2 C8 127.32(13) . . ?
C23 N3 C30 121.36(12) . . ?
C23 N3 C8 106.58(11) . . ?
C30 N3 C8 121.59(11) . . ?
C23 N4 N2 106.34(12) . . ?
C10 O2 C11 116.55(14) . . ?
C7 S1 C12 94.85(7) . . ?
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 C6 1.379(3) . ?
C1 C2 1.382(3) . ?
C1 N1 1.419(2) . ?
C2 C3 1.379(3) . ?
C3 C4 1.380(3) . ?
C4 C5 1.366(4) . ?
C5 C6 1.391(3) . ?
C7 N1 1.2632(19) . ?
C7 C8 1.548(2) . ?
C7 S1 1.7537(16) . ?
C8 N2 1.4591(18) . ?
C8 N3 1.4862(18) . ?
C8 C9 1.569(2) . ?
C9 C12 1.512(2) . ?
C9 C10 1.513(2) . ?
C10 O1 1.2002(18) . ?
C10 O2 1.3349(18) . ?
C11 O2 1.446(2) . ?
C12 C13 1.323(2) . ?
C12 S1 1.7733(16) . ?
C13 C14 1.506(2) . ?
C14 C16 1.519(3) . ?
C14 C15 1.518(3) . ?
C17 C22 1.390(2) . ?
C17 N2 1.3908(19) . ?
C17 C18 1.394(2) . ?
C18 C19 1.387(3) . ?
C19 C20 1.365(3) . ?
C20 C21 1.370(4) . ?
C21 C22 1.381(3) . ?
C23 N4 1.2830(18) . ?
C23 N3 1.4055(18) . ?
C23 C24 1.470(2) . ?
C24 C29 1.386(2) . ?
C24 C25 1.391(2) . ?
C25 C26 1.385(2) . ?
C26 C27 1.368(3) . ?
C27 C28 1.372(3) . ?
C28 C29 1.381(2) . ?
C30 C31 1.380(2) . ?
C30 C35 1.385(2) . ?
C30 N3 1.4412(18) . ?
C31 C32 1.389(2) . ?
C32 C33 1.367(3) . ?
C33 C34 1.372(3) . ?
C34 C35 1.383(2) . ?
C36 C37 1.470(7) . ?
C37 O3 1.212(4) . ?
C37 C38 1.437(6) . ?
N2 N4 1.3878(17) . ?
