#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/35/1503596.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_1503596
loop_
_publ_author_name
'Boyce, Gregory R.'
'Liu, Shubin'
'Johnson, Jeffrey S.'
_publ_section_title
;
 Construction of cyclopentanol derivatives via three-component coupling of
 silyl glyoxylates, acetylides, and nitroalkenes.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              652
_journal_page_last               655
_journal_paper_doi               10.1021/ol2033527
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C17 H21 N O5'
_chemical_formula_sum            'C17 H21 N O5'
_chemical_formula_weight         319.35
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_date             2011-04-27
_audit_creation_method
;
  Olex2 1.1-beta
  (compiled Feb 15 2011 20:38:53, GUI svn.r3494)
;
_cell_angle_alpha                100.0550(10)
_cell_angle_beta                 102.351(2)
_cell_angle_gamma                115.5310(10)
_cell_formula_units_Z            2
_cell_length_a                   8.7703(2)
_cell_length_b                   9.2477(2)
_cell_length_c                   12.0469(3)
_cell_measurement_reflns_used    6295
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      65.86
_cell_measurement_theta_min      3.94
_cell_volume                     820.86(4)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'smtbx-flip (Bourhis, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9007
_diffrn_reflns_theta_full        66.29
_diffrn_reflns_theta_max         66.29
_diffrn_reflns_theta_min         3.94
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  0.9521
_exptl_absorpt_correction_T_min  0.8062
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
 SADABS-2008/1 (Bruker,2008) was used for absorption correction.
 R(int) was 0.0463 before and 0.0383 after correction.
 The Ratio of minimum to maximum transmission is 0.846759794139.
 The λ/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.253
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         2789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0381
_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)+(0.0690P)²+0.2070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                2539
_reflns_number_total             2789
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2033527_si_001.cif
_cod_data_source_block           x1104027
_cod_original_cell_volume        820.86(3)
_cod_database_code               1503596
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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
C1 C -0.23955(19) 0.71763(17) 0.14430(12) 0.0254(3) Uani 1 1 d
C2 C -0.40706(19) 0.66267(18) 0.15687(14) 0.0287(3) Uani 1 1 d
C3 C -0.4244(2) 0.69130(18) 0.26940(14) 0.0289(3) Uani 1 1 d
C4 C -0.2724(2) 0.77451(17) 0.36926(13) 0.0262(3) Uani 1 1 d
C5 C -0.10445(19) 0.83010(17) 0.35655(12) 0.0224(3) Uani 1 1 d
C6 C -0.08516(18) 0.80362(16) 0.24436(12) 0.0213(3) Uani 1 1 d
C7 C 0.09813(18) 0.86817(16) 0.23074(11) 0.0209(3) Uani 1 1 d
C8 C 0.13197(18) 0.73742(17) 0.16055(12) 0.0226(3) Uani 1 1 d
C9 C 0.22023(18) 0.79528(18) 0.08771(12) 0.0235(3) Uani 1 1 d
C10 C 0.25828(18) 0.97098(17) 0.08906(12) 0.0228(3) Uani 1 1 d
C11 C 0.13624(18) 0.99367(17) 0.15856(11) 0.0218(3) Uani 1 1 d
C12 C 0.0735(2) 0.56937(18) 0.18059(13) 0.0270(3) Uani 1 1 d
O13 O 0.20770(15) 0.98332(14) -0.02694(8) 0.0281(3) Uani 1 1 d
C14 C 0.45703(18) 1.10170(17) 0.15222(12) 0.0222(3) Uani 1 1 d
O15 O 0.54843(13) 1.18368(13) 0.10073(9) 0.0282(3) Uani 1 1 d
O16 O 0.50444(12) 1.10731(11) 0.26556(8) 0.0223(2) Uani 1 1 d
C17 C 0.68782(18) 1.22901(17) 0.34968(12) 0.0231(3) Uani 1 1 d
C18 C 0.6766(2) 1.18485(19) 0.46450(13) 0.0285(3) Uani 1 1 d
C19 C 0.82453(19) 1.19680(19) 0.30754(13) 0.0263(3) Uani 1 1 d
C20 C 0.7180(2) 1.40617(19) 0.36193(14) 0.0301(3) Uani 1 1 d
N21 N 0.20798(16) 1.17306(15) 0.23013(11) 0.0252(3) Uani 1 1 d
O22 O 0.25604(16) 1.27848(14) 0.17737(11) 0.0371(3) Uani 1 1 d
O23 O 0.21303(15) 1.20507(13) 0.33385(9) 0.0332(3) Uani 1 1 d
H1 H -0.229(2) 0.697(2) 0.0667(17) 0.031(4) Uiso 1 1 d
H2 H -0.512(3) 0.602(2) 0.0875(17) 0.033(4) Uiso 1 1 d
H3 H -0.539(3) 0.651(2) 0.2787(16) 0.037(5) Uiso 1 1 d
H4 H -0.285(2) 0.788(2) 0.4468(16) 0.026(4) Uiso 1 1 d
H5 H 0.001(2) 0.890(2) 0.4250(14) 0.020(4) Uiso 1 1 d
H7 H 0.187(2) 0.920(2) 0.3073(15) 0.021(4) Uiso 1 1 d
H9 H 0.264(2) 0.739(2) 0.0390(16) 0.029(4) Uiso 1 1 d
H11 H 0.026(2) 0.9667(19) 0.0999(14) 0.021(4) Uiso 1 1 d
H13 H 0.299(3) 1.051(3) -0.037(2) 0.053(6) Uiso 1 1 d
H12A H 0.129(2) 0.581(2) 0.2640(17) 0.032(4) Uiso 1 1 d
H18A H 0.795(3) 1.259(2) 0.5257(17) 0.036(5) Uiso 1 1 d
H19A H 0.793(2) 1.079(2) 0.2943(15) 0.026(4) Uiso 1 1 d
H20A H 0.831(3) 1.487(2) 0.4261(17) 0.034(5) Uiso 1 1 d
H12B H -0.053(3) 0.512(2) 0.1657(16) 0.033(4) Uiso 1 1 d
H18B H 0.586(3) 1.203(2) 0.4904(16) 0.036(5) Uiso 1 1 d
H19B H 0.835(2) 1.221(2) 0.2340(16) 0.030(4) Uiso 1 1 d
H20B H 0.620(3) 1.420(2) 0.3865(17) 0.038(5) Uiso 1 1 d
H12C H 0.106(2) 0.501(2) 0.1307(17) 0.037(5) Uiso 1 1 d
H18C H 0.645(2) 1.066(2) 0.4518(15) 0.029(4) Uiso 1 1 d
H19C H 0.940(3) 1.261(2) 0.3677(18) 0.040(5) Uiso 1 1 d
H20C H 0.718(2) 1.435(2) 0.2878(17) 0.034(5) Uiso 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 0.0181 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 120.72(13)
C2 C1 H1 119.7(11)
C6 C1 H1 119.6(11)
C1 C2 C3 120.37(14)
C1 C2 H2 119.9(11)
C3 C2 H2 119.7(11)
C2 C3 H3 120.7(11)
C4 C3 C2 119.42(14)
C4 C3 H3 119.8(11)
C3 C4 C5 120.17(13)
C3 C4 H4 119.1(10)
C5 C4 H4 120.7(10)
C4 C5 C6 120.99(13)
C4 C5 H5 120.5(9)
C6 C5 H5 118.5(10)
C1 C6 C7 120.83(12)
C5 C6 C1 118.32(13)
C5 C6 C7 120.85(12)
C6 C7 C8 115.98(11)
C6 C7 C11 113.27(11)
C6 C7 H7 109.8(9)
C8 C7 C11 100.82(10)
C8 C7 H7 107.4(9)
C11 C7 H7 109.0(10)
C9 C8 C7 111.78(12)
C9 C8 C12 127.36(13)
C12 C8 C7 120.82(12)
C8 C9 C10 113.68(12)
C8 C9 H9 126.9(11)
C10 C9 H9 119.4(11)
C9 C10 C11 100.41(11)
C9 C10 C14 112.38(11)
O13 C10 C9 112.24(11)
O13 C10 C11 110.97(11)
O13 C10 C14 108.20(11)
C14 C10 C11 112.58(11)
C7 C11 C10 107.95(11)
C7 C11 H11 109.5(9)
C10 C11 H11 107.0(9)
N21 C11 C7 114.70(11)
N21 C11 C10 113.12(11)
N21 C11 H11 104.2(9)
C8 C12 H12A 111.1(10)
C8 C12 H12B 110.6(11)
C8 C12 H12C 111.2(11)
H12A C12 H12B 106.0(15)
H12A C12 H12C 108.0(15)
H12B C12 H12C 109.8(15)
C10 O13 H13 107.3(16)
O15 C14 C10 122.03(12)
O15 C14 O16 127.94(13)
O16 C14 C10 110.03(11)
C14 O16 C17 121.63(10)
O16 C17 C18 101.73(11)
O16 C17 C19 109.93(11)
O16 C17 C20 108.77(11)
C19 C17 C18 111.09(12)
C19 C17 C20 113.43(12)
C20 C17 C18 111.24(12)
C17 C18 H18A 107.3(11)
C17 C18 H18B 111.0(11)
C17 C18 H18C 109.6(10)
H18A C18 H18B 109.7(15)
H18A C18 H18C 110.4(15)
H18B C18 H18C 108.8(15)
C17 C19 H19A 110.2(10)
C17 C19 H19B 113.9(11)
C17 C19 H19C 110.3(12)
H19A C19 H19B 106.9(14)
H19A C19 H19C 106.4(15)
H19B C19 H19C 108.9(15)
C17 C20 H20A 109.7(11)
C17 C20 H20B 110.5(11)
C17 C20 H20C 112.9(11)
H20A C20 H20B 106.2(15)
H20A C20 H20C 110.3(15)
H20B C20 H20C 107.0(15)
O22 N21 C11 116.15(11)
O23 N21 C11 119.46(11)
O23 N21 O22 124.38(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.385(2)
C1 C6 1.399(2)
C1 H1 0.953(19)
C2 C3 1.389(2)
C2 H2 0.961(19)
C3 C4 1.386(2)
C3 H3 0.95(2)
C4 C5 1.389(2)
C4 H4 0.958(18)
C5 C6 1.3904(19)
C5 H5 0.955(17)
C6 C7 1.5123(19)
C7 C8 1.5247(18)
C7 C11 1.5354(18)
C7 H7 0.952(17)
C8 C9 1.324(2)
C8 C12 1.494(2)
C9 C10 1.507(2)
C9 H9 0.960(19)
C10 C11 1.5512(18)
C10 O13 1.4132(16)
C10 C14 1.5407(19)
C11 N21 1.5033(18)
C11 H11 0.969(17)
C12 H12A 0.982(19)
C12 H12B 0.96(2)
C12 H12C 0.97(2)
O13 H13 0.83(2)
C14 O15 1.2063(17)
C14 O16 1.3242(16)
O16 C17 1.4914(16)
C17 C18 1.520(2)
C17 C19 1.516(2)
C17 C20 1.517(2)
C18 H18A 0.99(2)
C18 H18B 0.98(2)
C18 H18C 0.986(18)
C19 H19A 0.971(18)
C19 H19B 0.965(19)
C19 H19C 0.96(2)
C20 H20A 0.984(19)
C20 H20B 1.02(2)
C20 H20C 0.977(19)
N21 O22 1.2283(16)
N21 O23 1.2194(16)
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
C1 C2 C3 C4 -0.4(2)
C1 C6 C7 C8 -56.30(16)
C1 C6 C7 C11 59.60(16)
C2 C1 C6 C5 1.0(2)
C2 C1 C6 C7 -178.22(13)
C2 C3 C4 C5 0.6(2)
C3 C4 C5 C6 0.0(2)
C4 C5 C6 C1 -0.75(19)
C4 C5 C6 C7 178.44(12)
C5 C6 C7 C8 124.53(13)
C5 C6 C7 C11 -119.56(13)
C6 C1 C2 C3 -0.4(2)
C6 C7 C8 C9 138.30(12)
C6 C7 C8 C12 -43.70(17)
C6 C7 C11 C10 -147.22(11)
C6 C7 C11 N21 85.68(14)
C7 C8 C9 C10 -2.18(16)
C7 C11 N21 O22 173.17(12)
C7 C11 N21 O23 -7.78(17)
C8 C7 C11 C10 -22.63(13)
C8 C7 C11 N21 -149.74(11)
C8 C9 C10 C11 -12.11(15)
C8 C9 C10 O13 -130.02(13)
C8 C9 C10 C14 107.75(13)
C9 C10 C11 C7 21.48(13)
C9 C10 C11 N21 149.50(10)
C9 C10 C14 O15 117.90(14)
C9 C10 C14 O16 -62.53(14)
C10 C11 N21 O22 48.76(16)
C10 C11 N21 O23 -132.19(13)
C10 C14 O16 C17 -177.05(10)
C11 C7 C8 C9 15.58(14)
C11 C7 C8 C12 -166.43(12)
C11 C10 C14 O15 -129.59(13)
C11 C10 C14 O16 49.98(15)
C12 C8 C9 C10 179.98(13)
O13 C10 C11 C7 140.33(11)
O13 C10 C11 N21 -91.65(13)
O13 C10 C14 O15 -6.59(18)
O13 C10 C14 O16 172.98(10)
C14 C10 C11 C7 -98.23(13)
C14 C10 C11 N21 29.79(15)
C14 O16 C17 C18 -179.09(12)
C14 O16 C17 C19 -61.31(15)
C14 O16 C17 C20 63.43(15)
O15 C14 O16 C17 2.5(2)
