#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/20/1502028.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_1502028
loop_
_publ_author_name
'Chen, Jinshui'
'Captain, Burjor'
'Takenaka, Norito'
_publ_section_title
;
 Helical chiral 2,2'-bipyridine N-monoxides as catalysts in the
 enantioselective propargylation of aldehydes with allenyltrichlorosilane.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1654
_journal_page_last               1657
_journal_paper_doi               10.1021/ol200102c
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C34 H20 N2 O'
_chemical_formula_weight         472.52
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3737(3)
_cell_length_b                   12.6257(5)
_cell_length_c                   21.4999(8)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.40
_cell_measurement_theta_min      2.49
_cell_volume                     2273.05(15)
_computing_cell_refinement       'SAINT+  V7.46A (Bruker, 2007)'
_computing_data_collection       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_data_reduction        'SAINT+  V7.46A (Bruker, 2007)'
_computing_molecular_graphics    'XSHELL v4.02 (Bruker, 2000)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       '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  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            24872
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9975
_exptl_absorpt_correction_T_min  0.9625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS 2007/4 Bruker)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         6036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0391
_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)+(0.0686P)²+0.1995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                5402
_reflns_number_total             6036
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200102c_si_001.cif
_cod_data_source_block           collect_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1502028
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
O1 O 0.98353(11) 0.53475(7) 0.78821(4) 0.0433(2) Uani 1 1 d .
N1 N 0.92567(13) 0.62658(8) 0.80321(5) 0.0391(2) Uani 1 1 d .
N2 N 1.1235(2) 0.69475(10) 0.94815(6) 0.0613(4) Uani 1 1 d .
C2 C 0.98328(16) 0.68153(10) 0.85295(6) 0.0413(3) Uani 1 1 d .
C3 C 0.9458(2) 0.79014(11) 0.85730(8) 0.0556(4) Uani 1 1 d .
H3 H 0.9823 0.8288 0.8912 0.067 Uiso 1 1 calc R
C4 C 0.8577(2) 0.83921(12) 0.81310(9) 0.0631(4) Uani 1 1 d .
H4 H 0.8459 0.9124 0.8138 0.076 Uiso 1 1 calc R
C5 C 0.6929(2) 0.82613(16) 0.71688(9) 0.0688(5) Uani 1 1 d .
H5 H 0.6776 0.8991 0.7160 0.083 Uiso 1 1 calc R
C6 C 0.6293(2) 0.76488(19) 0.67190(8) 0.0724(6) Uani 1 1 d .
H6 H 0.5815 0.7970 0.6377 0.087 Uiso 1 1 calc R
C7 C 0.5608(3) 0.5893(2) 0.62774(8) 0.0794(6) Uani 1 1 d .
H7 H 0.5049 0.6222 0.5957 0.095 Uiso 1 1 calc R
C8 C 0.5722(3) 0.4833(2) 0.62865(8) 0.0796(6) Uani 1 1 d .
H8 H 0.5371 0.4446 0.5945 0.095 Uiso 1 1 calc R
C9 C 0.6500(2) 0.31713(17) 0.68226(8) 0.0705(5) Uani 1 1 d .
H9 H 0.6144 0.2780 0.6483 0.085 Uiso 1 1 calc R
C10 C 0.7125(2) 0.26631(15) 0.73124(8) 0.0631(5) Uani 1 1 d .
H10 H 0.7335 0.1941 0.7286 0.076 Uiso 1 1 calc R
C11 C 0.81778(18) 0.26912(11) 0.84098(7) 0.0468(3) Uani 1 1 d .
C12 C 0.83284(18) 0.32355(10) 0.89779(7) 0.0445(3) Uani 1 1 d .
C13 C 0.74433(19) 0.47781(11) 0.96255(6) 0.0453(3) Uani 1 1 d .
H13 H 0.7928 0.4472 0.9971 0.054 Uiso 1 1 calc R
C14 C 0.6622(2) 0.57017(11) 0.96977(6) 0.0501(3) Uani 1 1 d .
H14 H 0.6575 0.6029 1.0085 0.060 Uiso 1 1 calc R
C15 C 0.5856(2) 0.61514(11) 0.91891(6) 0.0491(3) Uani 1 1 d .
H15 H 0.5239 0.6758 0.9240 0.059 Uiso 1 1 calc R
C16 C 0.60077(17) 0.56997(10) 0.86097(6) 0.0420(3) Uani 1 1 d .
H16 H 0.5488 0.6006 0.8272 0.050 Uiso 1 1 calc R
C17 C 0.78400(19) 0.77913(13) 0.76598(7) 0.0540(4) Uani 1 1 d .
C18 C 0.80396(16) 0.66857(11) 0.76578(6) 0.0438(3) Uani 1 1 d .
C19 C 0.6332(2) 0.65260(17) 0.67530(7) 0.0619(4) Uani 1 1 d .
C20 C 0.71006(16) 0.60147(13) 0.72596(6) 0.0475(3) Uani 1 1 d .
C21 C 0.6367(2) 0.42918(17) 0.68082(7) 0.0627(4) Uani 1 1 d .
C22 C 0.68715(17) 0.48825(13) 0.73351(6) 0.0478(3) Uani 1 1 d .
C23 C 0.74722(17) 0.32169(11) 0.78743(7) 0.0464(3) Uani 1 1 d .
C24 C 0.71325(15) 0.43039(11) 0.79026(6) 0.0408(3) Uani 1 1 d .
C25 C 0.75796(17) 0.42750(9) 0.90444(6) 0.0384(2) Uani 1 1 d .
C26 C 0.69342(15) 0.47822(9) 0.85173(5) 0.0363(2) Uani 1 1 d .
C27 C 0.8861(2) 0.16614(12) 0.83677(9) 0.0619(5) Uani 1 1 d .
H27 H 0.8753 0.1280 0.8000 0.074 Uiso 1 1 calc R
C28 C 0.9667(3) 0.12216(13) 0.88524(11) 0.0750(6) Uani 1 1 d .
H28 H 1.0119 0.0553 0.8809 0.090 Uiso 1 1 calc R
C29 C 0.9817(3) 0.17568(14) 0.94055(11) 0.0760(6) Uani 1 1 d .
H29 H 1.0371 0.1452 0.9735 0.091 Uiso 1 1 calc R
C30 C 0.9144(2) 0.27472(12) 0.94714(8) 0.0622(4) Uani 1 1 d .
H30 H 0.9231 0.3099 0.9850 0.075 Uiso 1 1 calc R
C31 C 1.08424(16) 0.62977(10) 0.90077(6) 0.0408(3) Uani 1 1 d .
C32 C 1.13024(19) 0.52384(11) 0.90132(7) 0.0507(3) Uani 1 1 d .
H32 H 1.1079 0.4801 0.8676 0.061 Uiso 1 1 calc R
C33 C 1.2097(2) 0.48477(13) 0.95285(8) 0.0591(4) Uani 1 1 d .
H33 H 1.2390 0.4138 0.9544 0.071 Uiso 1 1 calc R
C34 C 1.2452(2) 0.55032(14) 1.00128(7) 0.0614(4) Uani 1 1 d .
H34 H 1.2965 0.5251 1.0367 0.074 Uiso 1 1 calc R
C35 C 1.2025(3) 0.65458(15) 0.99600(8) 0.0710(5) Uani 1 1 d .
H35 H 1.2309 0.7002 1.0281 0.085 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 N1 C2 121.19(11)
O1 N1 C18 117.82(11)
C2 N1 C18 120.99(11)
C35 N2 C31 118.40(14)
N1 C2 C3 117.92(13)
N1 C2 C31 121.42(11)
C3 C2 C31 120.65(13)
C4 C3 C2 121.35(16)
C3 C4 C17 119.84(14)
C6 C5 C17 120.13(18)
C5 C6 C19 121.78(15)
C8 C7 C19 121.05(18)
C7 C8 C21 121.24(18)
C10 C9 C21 121.68(15)
C9 C10 C23 120.72(17)
C12 C11 C27 117.74(15)
C12 C11 C23 120.04(12)
C27 C11 C23 121.99(14)
C30 C12 C11 119.01(13)
C30 C12 C25 121.93(13)
C11 C12 C25 119.02(13)
C14 C13 C25 121.92(13)
C13 C14 C15 119.56(12)
C16 C15 C14 120.03(13)
C15 C16 C26 121.31(12)
C18 C17 C4 119.00(14)
C18 C17 C5 118.22(18)
C4 C17 C5 122.76(16)
N1 C18 C17 117.39(14)
N1 C18 C20 121.06(13)
C17 C18 C20 121.44(14)
C6 C19 C20 120.25(17)
C6 C19 C7 120.68(17)
C20 C19 C7 119.07(19)
C19 C20 C18 115.88(15)
C19 C20 C22 118.26(15)
C18 C20 C22 125.86(12)
C9 C21 C22 118.86(16)
C9 C21 C8 121.78(17)
C22 C21 C8 119.35(19)
C21 C22 C24 117.05(15)
C21 C22 C20 117.85(14)
C24 C22 C20 125.09(12)
C24 C23 C10 118.37(15)
C24 C23 C11 119.64(12)
C10 C23 C11 121.99(14)
C23 C24 C22 119.39(12)
C23 C24 C26 117.79(12)
C22 C24 C26 122.64(12)
C13 C25 C26 118.56(11)
C13 C25 C12 121.83(12)
C26 C25 C12 119.59(11)
C16 C26 C25 118.13(11)
C16 C26 C24 121.99(11)
C25 C26 C24 119.70(11)
C28 C27 C11 121.57(16)
C27 C28 C29 120.53(15)
C28 C29 C30 119.84(19)
C29 C30 C12 121.29(18)
N2 C31 C32 120.70(13)
N2 C31 C2 113.24(12)
C32 C31 C2 125.97(12)
C33 C32 C31 118.86(14)
C34 C33 C32 120.01(15)
C33 C34 C35 117.64(15)
N2 C35 C34 124.28(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.2972(14)
N1 C2 1.3631(17)
N1 C18 1.4025(17)
N2 C35 1.324(2)
N2 C31 1.3489(18)
C2 C3 1.4099(19)
C2 C31 1.483(2)
C3 C4 1.353(2)
C4 C17 1.408(3)
C5 C6 1.348(3)
C5 C17 1.431(2)
C6 C19 1.420(3)
C7 C8 1.342(3)
C7 C19 1.432(3)
C8 C21 1.421(3)
C9 C10 1.340(3)
C9 C21 1.419(3)
C10 C23 1.4258(19)
C11 C12 1.407(2)
C11 C27 1.423(2)
C11 C23 1.454(2)
C12 C30 1.404(2)
C12 C25 1.4615(17)
C13 C14 1.363(2)
C13 C25 1.4062(17)
C14 C15 1.389(2)
C15 C16 1.3759(18)
C16 C26 1.4084(18)
C17 C18 1.406(2)
C18 C20 1.438(2)
C19 C20 1.420(2)
C20 C22 1.451(2)
C21 C22 1.420(2)
C22 C24 1.4388(19)
C23 C24 1.403(2)
C24 C26 1.4624(16)
C25 C26 1.4095(17)
C27 C28 1.360(3)
C28 C29 1.374(3)
C29 C30 1.379(2)
C31 C32 1.3918(19)
C32 C33 1.383(2)
C33 C34 1.363(2)
C34 C35 1.369(3)
