#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:55:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178411 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/32/4023294.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_4023294
loop_
_publ_author_name
'Rui Ramalho'
'Peter J. Jervis'
'Benson M. Kariuki'
'Alexander C. Humphries'
'Liam R. Cox'
_publ_section_title
;
 A Brønsted Acid Mediated Cascade Enone Synthesis from Aldehydes
 Containing a Tethered Propargylsilane
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1631
_journal_page_last               1634
_journal_paper_doi               10.1021/jo702351s
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C21 H29 N O5 Si'
_chemical_formula_sum            'C21 H29 N O5 Si'
_chemical_formula_weight         403.54
_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                 90.322(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.8890(5)
_cell_length_b                   8.0262(3)
_cell_length_c                   18.0566(6)
_cell_measurement_reflns_used    2829
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      70.6
_cell_measurement_theta_min      2.78
_cell_volume                     2302.69(14)
_computing_cell_refinement       SAINTPLUS
_computing_data_collection       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_measurement_method       'CCD slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0887
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13619
_diffrn_reflns_theta_full        70.60
_diffrn_reflns_theta_max         70.60
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    1.141
_exptl_absorpt_correction_T_max  0.8209
_exptl_absorpt_correction_T_min  0.8039
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4197
_refine_ls_number_restraints     234
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0702
_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)+(0.0800P)²+1.0974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2109
_refine_ls_wR_factor_ref         0.2323
_reflns_number_gt                2829
_reflns_number_total             4197
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702351s-File004.cif
_cod_data_source_block           rr5144
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023294
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 0.45418(19) 0.5092(4) 0.38739(17) 0.0681(8) Uani 1 1 d U . .
C2 C 0.4064(2) 0.5548(4) 0.44801(17) 0.0711(8) Uani 1 1 d U . .
H2 H 0.3945 0.6660 0.4580 0.085 Uiso 1 1 calc R . .
C3 C 0.37694(19) 0.4280(4) 0.49335(17) 0.0705(8) Uani 1 1 d U . .
H3 H 0.3442 0.4542 0.5343 0.085 Uiso 1 1 calc R . .
C4 C 0.39561(19) 0.2637(4) 0.47849(16) 0.0655(7) Uani 1 1 d U . .
C5 C 0.4439(2) 0.2230(4) 0.41730(18) 0.0749(9) Uani 1 1 d U . .
H5 H 0.4568 0.1122 0.4075 0.090 Uiso 1 1 calc R . .
C6 C 0.4725(2) 0.3471(4) 0.37102(18) 0.0754(9) Uani 1 1 d U . .
H6 H 0.5039 0.3208 0.3293 0.090 Uiso 1 1 calc R . .
C7 C 0.3670(2) 0.1239(4) 0.52732(19) 0.0736(8) Uani 1 1 d U . .
C8 C 0.2954(2) 0.0614(4) 0.64118(19) 0.0790(9) Uani 1 1 d U . .
H8 H 0.3328 -0.0356 0.6434 0.095 Uiso 1 1 calc R . .
C9 C 0.2076(2) 0.0088(4) 0.61810(19) 0.0809(9) Uani 1 1 d U . .
C10 C 0.2507(2) 0.3160(4) 0.7137(2) 0.0816(10) Uani 1 1 d U . .
H10 H 0.2830 0.3920 0.6823 0.098 Uiso 1 1 calc R . .
C11 C 0.2958(3) 0.1519(4) 0.7142(2) 0.0860(10) Uani 1 1 d U . .
H11A H 0.2702 0.0807 0.7511 0.103 Uiso 1 1 calc R . .
H11B H 0.3538 0.1706 0.7292 0.103 Uiso 1 1 calc R . .
C12 C 0.1939(3) -0.1426(5) 0.5945(2) 0.0931(11) Uani 1 1 d U . .
C13 C 0.1757(5) -0.2891(6) 0.5717(3) 0.1334(19) Uani 1 1 d DU . .
H13A H 0.175(4) -0.309(6) 0.5199(7) 0.160 Uiso 1 1 d D . .
H13B H 0.165(4) -0.391(3) 0.597(2) 0.160 Uiso 1 1 d D . .
C14 C 0.0729(10) 0.240(2) 0.5487(10) 0.139(6) Uani 0.589(14) 1 d PDU . .
H14A H 0.0363 0.1530 0.5296 0.167 Uiso 0.589(14) 1 calc PR . .
H14B H 0.0375 0.3343 0.5612 0.167 Uiso 0.589(14) 1 calc PR . .
C15 C 0.1311(8) 0.2923(13) 0.4879(7) 0.147(5) Uani 0.589(14) 1 d PDU . .
H15A H 0.0987 0.3328 0.4466 0.221 Uiso 0.589(14) 1 calc PR . .
H15B H 0.1642 0.1985 0.4725 0.221 Uiso 0.589(14) 1 calc PR . .
H15C H 0.1676 0.3790 0.5056 0.221 Uiso 0.589(14) 1 calc PR . .
C16 C 0.0330(3) 0.0693(8) 0.6850(5) 0.155(2) Uani 1 1 d U . .
H16A H -0.0134 0.1480 0.6846 0.186 Uiso 1 1 calc R . .
H16B H 0.0146 -0.0292 0.6583 0.186 Uiso 1 1 calc R . .
C17 C 0.0507(6) 0.0220(12) 0.7624(6) 0.223(4) Uani 1 1 d U . .
H17A H 0.0012 -0.0257 0.7839 0.335 Uiso 1 1 calc R . .
H17B H 0.0671 0.1190 0.7900 0.335 Uiso 1 1 calc R . .
H17C H 0.0956 -0.0582 0.7637 0.335 Uiso 1 1 calc R . .
C18 C 0.2479(3) 0.3928(5) 0.7914(2) 0.0968(12) Uani 1 1 d U . .
H18A H 0.2073 0.3312 0.8205 0.116 Uiso 1 1 calc R . .
H18B H 0.3026 0.3772 0.8146 0.116 Uiso 1 1 calc R . .
C19 C 0.2263(3) 0.5715(6) 0.7955(2) 0.1027(12) Uani 1 1 d U . .
H19 H 0.1744 0.5894 0.7671 0.123 Uiso 1 1 calc R . .
C20 C 0.2108(5) 0.6256(8) 0.8752(3) 0.149(2) Uani 1 1 d U . .
H20A H 0.1618 0.5701 0.8938 0.223 Uiso 1 1 calc R . .
H20B H 0.2022 0.7440 0.8768 0.223 Uiso 1 1 calc R . .
H20C H 0.2587 0.5969 0.9053 0.223 Uiso 1 1 calc R . .
C21 C 0.2953(4) 0.6794(6) 0.7618(3) 0.142(2) Uani 1 1 d U . .
H21A H 0.3471 0.6618 0.7883 0.213 Uiso 1 1 calc R . .
H21B H 0.2795 0.7946 0.7653 0.213 Uiso 1 1 calc R . .
H21C H 0.3026 0.6498 0.7108 0.213 Uiso 1 1 calc R . .
N1 N 0.48667(19) 0.6413(5) 0.33961(17) 0.0855(9) Uani 1 1 d U . .
O1 O 0.5143(3) 0.6011(4) 0.28008(18) 0.1361(13) Uani 1 1 d U . .
O2 O 0.48476(19) 0.7843(4) 0.36129(17) 0.1042(9) Uani 1 1 d U . .
O3 O 0.37883(18) -0.0203(3) 0.51536(16) 0.0977(8) Uani 1 1 d U . .
O4 O 0.32682(14) 0.1830(3) 0.58718(12) 0.0767(6) Uani 1 1 d U . .
O5 O 0.16699(18) 0.3088(3) 0.68433(16) 0.0988(8) Uani 1 1 d U . .
Si1 Si 0.12256(7) 0.16332(14) 0.63438(7) 0.0946(4) Uani 1 1 d U . .
C15A C 0.0537(18) 0.176(3) 0.4910(17) 0.164(10) Uani 0.246(9) 1 d PDU . .
H15D H 0.0497 0.2333 0.4443 0.245 Uiso 0.246(9) 1 calc PR . .
H15E H -0.0017 0.1614 0.5109 0.245 Uiso 0.246(9) 1 calc PR . .
H15F H 0.0796 0.0696 0.4838 0.245 Uiso 0.246(9) 1 calc PR . .
C14A C 0.1057(13) 0.277(3) 0.5437(14) 0.129(6) Uani 0.246(9) 1 d PDU . .
H14C H 0.0778 0.3827 0.5531 0.155 Uiso 0.246(9) 1 calc PR . .
H14D H 0.1599 0.3013 0.5214 0.155 Uiso 0.246(9) 1 calc PR . .
C14B C 0.1057(13) 0.277(3) 0.5437(14) 0.129(6) Uani 0.164(6) 1 d PDU . .
H14E H 0.1484 0.3634 0.5395 0.155 Uiso 0.164(6) 1 calc PR . .
H14F H 0.1144 0.1993 0.5034 0.155 Uiso 0.164(6) 1 calc PR . .
C15B C 0.0212(18) 0.357(4) 0.534(2) 0.168(14) Uani 0.164(6) 1 d PDU . .
H15G H 0.0187 0.4107 0.4861 0.251 Uiso 0.164(6) 1 calc PR . .
H15H H 0.0124 0.4376 0.5719 0.251 Uiso 0.164(6) 1 calc PR . .
H15I H -0.0218 0.2728 0.5361 0.251 Uiso 0.164(6) 1 calc PR . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 '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 122.8(3) . . ?
C6 C1 N1 119.1(3) . . ?
C2 C1 N1 118.2(3) . . ?
C1 C2 C3 117.4(3) . . ?
C4 C3 C2 120.8(3) . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 C7 122.3(3) . . ?
C5 C4 C7 117.5(3) . . ?
C6 C5 C4 119.9(3) . . ?
C1 C6 C5 119.0(3) . . ?
O3 C7 O4 124.3(3) . . ?
O3 C7 C4 124.8(3) . . ?
O4 C7 C4 110.9(3) . . ?
O4 C8 C11 105.1(3) . . ?
O4 C8 C9 108.6(3) . . ?
C11 C8 C9 112.0(3) . . ?
C12 C9 C8 120.1(4) . . ?
C12 C9 Si1 123.5(3) . . ?
C8 C9 Si1 116.1(2) . . ?
O5 C10 C11 114.2(3) . . ?
O5 C10 C18 108.9(3) . . ?
C11 C10 C18 111.4(3) . . ?
C10 C11 C8 114.8(3) . . ?
C13 C12 C9 176.5(6) . . ?
C15 C14 Si1 116.5(12) . . ?
C17 C16 Si1 115.4(5) . . ?
C19 C18 C10 116.3(3) . . ?
C18 C19 C21 111.4(4) . . ?
C18 C19 C20 111.2(4) . . ?
C21 C19 C20 109.5(4) . . ?
O1 N1 O2 123.4(3) . . ?
O1 N1 C1 117.5(4) . . ?
O2 N1 C1 119.1(3) . . ?
C7 O4 C8 117.6(2) . . ?
C10 O5 Si1 129.2(2) . . ?
O5 Si1 C14 114.1(5) . . ?
O5 Si1 C16 110.4(3) . . ?
C14 Si1 C16 102.9(5) . . ?
O5 Si1 C9 104.60(16) . . ?
C14 Si1 C9 113.5(6) . . ?
C16 Si1 C9 111.5(2) . . ?
O5 Si1 C14A 101.0(7) . . ?
C14 Si1 C14A 18.7(7) . . ?
C16 Si1 C14A 121.2(7) . . ?
C9 Si1 C14A 106.6(7) . . ?
C15A C14A Si1 111(2) . . ?
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 1.366(5) . ?
C1 C2 1.385(4) . ?
C1 N1 1.463(4) . ?
C2 C3 1.389(4) . ?
C3 C4 1.378(4) . ?
C4 C5 1.387(4) . ?
C4 C7 1.499(4) . ?
C5 C6 1.380(5) . ?
C7 O3 1.193(4) . ?
C7 O4 1.345(4) . ?
C8 O4 1.469(4) . ?
C8 C11 1.505(5) . ?
C8 C9 1.514(5) . ?
C9 C12 1.306(5) . ?
C9 Si1 1.859(4) . ?
C10 O5 1.431(5) . ?
C10 C11 1.500(5) . ?
C10 C18 1.534(5) . ?
C12 C13 1.278(6) . ?
C14 C15 1.499(6) . ?
C14 Si1 1.84(2) . ?
C16 C17 1.474(10) . ?
C16 Si1 1.856(6) . ?
C18 C19 1.476(6) . ?
C19 C21 1.525(7) . ?
C19 C20 1.525(6) . ?
N1 O1 1.207(4) . ?
N1 O2 1.213(4) . ?
O5 Si1 1.634(3) . ?
Si1 C14A 1.89(3) . ?
C15A C14A 1.496(6) . ?
