#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/27/4022712.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_4022712
loop_
_publ_author_name
'François Couty'
'Olivier David'
'Bénédicte Larmanjat'
'Jérôme Marrot'
_publ_contact_author
;
      Dr O. David 
      Institut Lavoisier de Versailles, UMR 8180
      Université de Versailles 
      45 Avenue des Etats Unis
      78035 Versailles cedex
      France
;
_publ_contact_author_email       odavid@chimie.uvsq.fr
_publ_contact_author_fax         '(33) 01 39 25 44 52'
_publ_contact_author_phone       '(33) 01 39 25 44 55'
_publ_section_title
;
 Strained Azetidinium Ylides: New Reagents for Cyclopropanation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1058
_journal_page_last               1061
_journal_paper_doi               10.1021/jo062221e
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C18 H24 N2 O2'
_chemical_formula_weight         300.39
_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                   8.5497(3)
_cell_length_b                   13.0555(5)
_cell_length_c                   15.7323(7)
_cell_measurement_reflns_used    2889
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.75
_cell_measurement_theta_min      2.59
_cell_volume                     1756.05(12)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 512x512
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17574
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_correction_T_min  0.9882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2.10)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0445
_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)+(0.0612P)²+0.0243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1235
_reflns_number_gt                1630
_reflns_number_total             2888
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062221esi20061106_071339_3.cif
_cod_data_source_block           33b
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4022712
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
C1 C 0.7777(3) 0.07829(19) 0.91976(16) 0.0611(7) Uani 1 1 d .
H1 H 0.7946 0.0117 0.9010 0.073 Uiso 1 1 calc R
C2 C 0.7870(4) 0.0994(2) 1.00564(18) 0.0744(8) Uani 1 1 d .
H2 H 0.8106 0.0472 1.0438 0.089 Uiso 1 1 calc R
C3 C 0.7620(4) 0.1959(3) 1.0345(2) 0.0846(9) Uani 1 1 d .
H3 H 0.7689 0.2104 1.0923 0.102 Uiso 1 1 calc R
C4 C 0.7268(6) 0.2709(3) 0.9782(2) 0.1058(14) Uani 1 1 d .
H4 H 0.7093 0.3371 0.9978 0.127 Uiso 1 1 calc R
C5 C 0.7163(4) 0.25082(19) 0.89193(18) 0.0772(9) Uani 1 1 d .
H5 H 0.6906 0.3033 0.8545 0.093 Uiso 1 1 calc R
C6 C 0.7438(2) 0.15379(16) 0.86113(14) 0.0461(5) Uani 1 1 d .
C7 C 0.7393(2) 0.13294(14) 0.76657(14) 0.0420(5) Uani 1 1 d .
H7 H 0.7106 0.1972 0.7384 0.050 Uiso 1 1 calc R
C8 C 0.6136(2) 0.05350(14) 0.74396(13) 0.0412(5) Uani 1 1 d .
C9 C 0.4866(3) 0.07130(17) 0.67846(14) 0.0470(5) Uani 1 1 d .
H9 H 0.4507 0.0085 0.6504 0.056 Uiso 1 1 calc R
C10 C 0.4450(2) 0.07678(16) 0.77083(14) 0.0446(5) Uani 1 1 d .
H10 H 0.4272 0.1459 0.7931 0.053 Uiso 1 1 calc R
C11 C 0.6623(3) -0.05222(17) 0.75281(16) 0.0525(6) Uani 1 1 d .
N12 N 0.7026(3) -0.13478(16) 0.76048(19) 0.0850(8) Uani 1 1 d .
C13 C 0.9032(3) 0.10214(18) 0.73370(15) 0.0512(6) Uani 1 1 d .
H13 H 0.9337 0.0405 0.7651 0.061 Uiso 1 1 calc R
C14 C 1.0244(3) 0.1847(2) 0.7552(2) 0.0805(9) Uani 1 1 d .
H14A H 0.9890 0.2498 0.7342 0.121 Uiso 1 1 calc R
H14B H 1.1225 0.1677 0.7291 0.121 Uiso 1 1 calc R
H14C H 1.0374 0.1885 0.8157 0.121 Uiso 1 1 calc R
N15 N 0.8979(2) 0.07350(16) 0.64308(13) 0.0584(5) Uani 1 1 d .
C16 C 1.0211(3) 0.0000(3) 0.6223(2) 0.0854(9) Uani 1 1 d .
H16A H 1.1214 0.0303 0.6332 0.128 Uiso 1 1 calc R
H16B H 1.0138 -0.0183 0.5633 0.128 Uiso 1 1 calc R
H16C H 1.0089 -0.0602 0.6566 0.128 Uiso 1 1 calc R
C17 C 0.8997(4) 0.1594(3) 0.5849(2) 0.0839(9) Uani 1 1 d .
H17A H 1.0033 0.1877 0.5825 0.126 Uiso 1 1 calc R
H17B H 0.8279 0.2108 0.6044 0.126 Uiso 1 1 calc R
H17C H 0.8693 0.1366 0.5293 0.126 Uiso 1 1 calc R
C18 C 0.4798(3) 0.16455(19) 0.62267(18) 0.0643(7) Uani 1 1 d .
H18A H 0.5122 0.2235 0.6546 0.096 Uiso 1 1 calc R
H18B H 0.3746 0.1743 0.6029 0.096 Uiso 1 1 calc R
H18C H 0.5482 0.1554 0.5749 0.096 Uiso 1 1 calc R
C19 C 0.3487(3) -0.00487(18) 0.81000(15) 0.0480(5) Uani 1 1 d .
O20 O 0.3303(2) -0.08909(13) 0.78224(13) 0.0782(6) Uani 1 1 d .
O21 O 0.2847(2) 0.02675(12) 0.88215(12) 0.0696(5) Uani 1 1 d .
C22 C 0.1891(4) -0.0479(2) 0.9255(2) 0.0903(11) Uani 1 1 d .
H22A H 0.2534 -0.1041 0.9437 0.135 Uiso 1 1 calc R
H22B H 0.1097 -0.0726 0.8875 0.135 Uiso 1 1 calc R
H22C H 0.1408 -0.0166 0.9741 0.135 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C6 C1 C2 121.6(3)
C6 C1 H1 119.2
C2 C1 H1 119.2
C3 C2 C1 120.2(3)
C3 C2 H2 119.9
C1 C2 H2 119.9
C4 C3 C2 119.2(3)
C4 C3 H3 120.4
C2 C3 H3 120.4
C3 C4 C5 121.2(3)
C3 C4 H4 119.4
C5 C4 H4 119.4
C6 C5 C4 120.5(3)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C1 117.2(2)
C5 C6 C7 120.5(2)
C1 C6 C7 122.3(2)
C6 C7 C8 111.54(17)
C6 C7 C13 110.64(18)
C8 C7 C13 112.40(17)
C6 C7 H7 107.3
C8 C7 H7 107.3
C13 C7 H7 107.3
C11 C8 C9 114.68(18)
C11 C8 C10 115.64(18)
C9 C8 C10 58.87(15)
C11 C8 C7 114.85(19)
C9 C8 C7 123.76(18)
C10 C8 C7 117.42(16)
C10 C9 C18 121.3(2)
C10 C9 C8 61.15(14)
C18 C9 C8 123.33(19)
C10 C9 H9 113.7
C18 C9 H9 113.7
C8 C9 H9 113.7
C19 C10 C9 120.08(19)
C19 C10 C8 119.67(18)
C9 C10 C8 59.98(14)
C19 C10 H10 115.3
C9 C10 H10 115.3
C8 C10 H10 115.3
N12 C11 C8 178.9(3)
N15 C13 C14 114.3(2)
N15 C13 C7 111.20(19)
C14 C13 C7 110.8(2)
N15 C13 H13 106.7
C14 C13 H13 106.7
C7 C13 H13 106.7
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C17 N15 C16 111.1(2)
C17 N15 C13 114.5(2)
C16 N15 C13 111.2(2)
N15 C16 H16A 109.5
N15 C16 H16B 109.5
H16A C16 H16B 109.5
N15 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
N15 C17 H17A 109.5
N15 C17 H17B 109.5
H17A C17 H17B 109.5
N15 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C9 C18 H18A 109.5
C9 C18 H18B 109.5
H18A C18 H18B 109.5
C9 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
O20 C19 O21 123.1(2)
O20 C19 C10 125.7(2)
O21 C19 C10 111.20(19)
C19 O21 C22 115.35(19)
O21 C22 H22A 109.5
O21 C22 H22B 109.5
H22A C22 H22B 109.5
O21 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.381(3)
C1 C2 1.381(4)
C1 H1 0.9300
C2 C3 1.357(4)
C2 H2 0.9300
C3 C4 1.354(5)
C3 H3 0.9300
C4 C5 1.385(4)
C4 H4 0.9300
C5 C6 1.376(3)
C5 H5 0.9300
C6 C7 1.513(3)
C7 C8 1.535(3)
C7 C13 1.547(3)
C7 H7 0.9800
C8 C11 1.448(3)
C8 C9 1.515(3)
C8 C10 1.532(3)
C9 C10 1.498(3)
C9 C18 1.502(3)
C9 H9 0.9800
C10 C19 1.481(3)
C10 H10 0.9800
C11 N12 1.138(3)
C13 N15 1.475(3)
C13 C14 1.533(4)
C13 H13 0.9800
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
N15 C17 1.447(3)
N15 C16 1.462(3)
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C19 O20 1.193(3)
C19 O21 1.326(3)
O21 C22 1.442(3)
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17264293
