#------------------------------------------------------------------------------
#$Date: 2016-03-21 01:46:57 +0100 (lun 21 de mar de 2016) $
#$Revision: 178405 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/26/4022602.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_4022602
loop_
_publ_author_name
'Guillaume Bélanger'
'Myriam April'
'Étienne Dauphin'
'Stéphanie Roy'
_publ_section_title
;
 Effect of Substitution on the Intramolecular 1,3-Dipolar
 Cycloaddition of Alkene Tethered Münchnones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1104
_journal_page_last               1111
_journal_paper_doi               10.1021/jo061556t
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C14 H15 N O2'
_chemical_formula_weight         229.27
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2006-08-15T08:32:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 94.64(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.362(3)
_cell_length_b                   16.675(7)
_cell_length_c                   10.895(5)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      12.5
_cell_volume                     1152.0(9)
_computing_cell_refinement       Difrac
_computing_data_collection       Difrac
_computing_data_reduction        NRCVAX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       Omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2045
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_correction_T_min  0.9571
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Psi Scan'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0139(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0460P)²+0.2233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.1007
_reflns_number_gt                1497
_reflns_number_total             2045
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061556tsi20061212_052328.cif
_cod_data_source_block           ed-02-076c
_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 'Empirical' changed to
'empirical' 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/n'
_cod_database_code               4022602
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C -0.0443(3) 0.63535(11) 0.37505(18) 0.0521(5) Uani 1 1 d .
C4 C 0.0372(2) 0.75487(10) 0.46096(14) 0.0400(4) Uani 1 1 d .
C5 C 0.1397(3) 0.72490(11) 0.58616(16) 0.0502(5) Uani 1 1 d .
H5 H 0.2937 0.7288 0.5975 0.06 Uiso 1 1 calc R
C6 C 0.0483(3) 0.64014(11) 0.59071(18) 0.0564(5) Uani 1 1 d .
H6A H 0.0047 0.6274 0.6717 0.068 Uiso 1 1 calc R
H6B H 0.148 0.6001 0.5671 0.068 Uiso 1 1 calc R
C7 C -0.1448(3) 0.64750(10) 0.49326(16) 0.0463(4) Uani 1 1 d .
C8 C -0.3352(3) 0.59648(12) 0.5093(2) 0.0653(5) Uani 1 1 d .
H8A H -0.3885 0.6082 0.5873 0.098 Uiso 1 1 calc R
H8B H -0.2967 0.5409 0.5065 0.098 Uiso 1 1 calc R
H8C H -0.4421 0.6078 0.4443 0.098 Uiso 1 1 calc R
C10 C -0.2056(3) 0.77088(11) 0.60713(16) 0.0508(5) Uani 1 1 d .
H10A H -0.2934 0.7368 0.654 0.061 Uiso 1 1 calc R
H10B H -0.2697 0.8236 0.5995 0.061 Uiso 1 1 calc R
C11 C 0.0191(3) 0.77661(12) 0.67105(16) 0.0575(5) Uani 1 1 d .
H11A H 0.0702 0.8314 0.6737 0.069 Uiso 1 1 calc R
H11B H 0.0261 0.755 0.7539 0.069 Uiso 1 1 calc R
C12 C 0.0795(3) 0.83828(10) 0.42003(15) 0.0420(4) Uani 1 1 d .
C13 C -0.0821(3) 0.88570(11) 0.36936(17) 0.0521(5) Uani 1 1 d .
H13 H -0.2195 0.8662 0.3634 0.062 Uiso 1 1 calc R
C14 C -0.0426(3) 0.96199(11) 0.32728(18) 0.0613(5) Uani 1 1 d .
H14 H -0.1532 0.9936 0.2939 0.074 Uiso 1 1 calc R
C15 C 0.1587(3) 0.99090(12) 0.33462(18) 0.0612(5) Uani 1 1 d .
H15 H 0.1852 1.0422 0.3059 0.073 Uiso 1 1 calc R
C16 C 0.3212(3) 0.94459(12) 0.38407(19) 0.0614(5) Uani 1 1 d .
H16 H 0.4584 0.9643 0.3886 0.074 Uiso 1 1 calc R
C17 C 0.2827(3) 0.86855(11) 0.42738(18) 0.0550(5) Uani 1 1 d .
H17 H 0.394 0.8375 0.4617 0.066 Uiso 1 1 calc R
N9 N -0.1824(2) 0.73583(8) 0.48353(12) 0.0400(3) Uani 1 1 d .
O2 O -0.0509(2) 0.57979(9) 0.30547(14) 0.0763(5) Uani 1 1 d .
O3 O 0.07915(19) 0.70042(7) 0.36129(11) 0.0501(3) 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 0 '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 0.006 '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
O2 C1 O3 122.76(17)
O2 C1 C7 130.91(18)
O3 C1 C7 106.17(14)
O3 C4 N9 102.91(12)
O3 C4 C12 108.06(13)
N9 C4 C12 116.58(13)
O3 C4 C5 111.51(13)
N9 C4 C5 96.95(13)
C12 C4 C5 119.45(14)
C11 C5 C6 107.03(16)
C11 C5 C4 98.98(14)
C6 C5 C4 101.12(14)
C5 C6 C7 100.68(13)
N9 C7 C1 98.59(13)
N9 C7 C8 116.15(15)
C1 C7 C8 115.34(16)
N9 C7 C6 103.77(13)
C1 C7 C6 101.93(15)
C8 C7 C6 118.28(16)
N9 C10 C11 106.08(14)
C5 C11 C10 100.70(14)
C13 C12 C17 118.53(16)
C13 C12 C4 120.55(15)
C17 C12 C4 120.87(16)
C12 C13 C14 120.76(17)
C15 C14 C13 120.07(19)
C14 C15 C16 120.02(19)
C15 C16 C17 120.27(18)
C16 C17 C12 120.37(18)
C4 N9 C10 103.40(13)
C4 N9 C7 94.35(12)
C10 N9 C7 110.51(13)
C1 O3 C4 105.90(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.196(2)
C1 O3 1.355(2)
C1 C7 1.497(3)
C4 O3 1.4565(19)
C4 N9 1.473(2)
C4 C12 1.492(2)
C4 C5 1.546(2)
C5 C11 1.517(3)
C5 C6 1.531(3)
C6 C7 1.562(3)
C7 N9 1.494(2)
C7 C8 1.502(3)
C10 N9 1.486(2)
C10 C11 1.542(3)
C12 C13 1.377(2)
C12 C17 1.384(2)
C13 C14 1.382(3)
C14 C15 1.364(3)
C15 C16 1.366(3)
C16 C17 1.382(3)
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
O3 C4 C5 C11 -164.03(13)
N9 C4 C5 C11 -57.17(15)
C12 C4 C5 C11 68.73(18)
O3 C4 C5 C6 -54.57(17)
N9 C4 C5 C6 52.29(15)
C12 C4 C5 C6 178.19(14)
C11 C5 C6 C7 84.29(17)
C4 C5 C6 C7 -18.80(17)
O2 C1 C7 N9 -146.6(2)
O3 C1 C7 N9 38.05(17)
O2 C1 C7 C8 -22.2(3)
O3 C1 C7 C8 162.42(16)
O2 C1 C7 C6 107.3(2)
O3 C1 C7 C6 -68.10(16)
C5 C6 C7 N9 -19.89(17)
C5 C6 C7 C1 82.17(16)
C5 C6 C7 C8 -150.22(16)
C6 C5 C11 C10 -62.23(17)
C4 C5 C11 C10 42.40(17)
N9 C10 C11 C5 -13.15(18)
O3 C4 C12 C13 95.42(18)
N9 C4 C12 C13 -19.8(2)
C5 C4 C12 C13 -135.75(17)
O3 C4 C12 C17 -81.90(19)
N9 C4 C12 C17 162.89(15)
C5 C4 C12 C17 46.9(2)
C17 C12 C13 C14 -0.3(3)
C4 C12 C13 C14 -177.68(16)
C12 C13 C14 C15 0.6(3)
C13 C14 C15 C16 -0.3(3)
C14 C15 C16 C17 -0.3(3)
C15 C16 C17 C12 0.6(3)
C13 C12 C17 C16 -0.3(3)
C4 C12 C17 C16 177.07(16)
O3 C4 N9 C10 162.94(12)
C12 C4 N9 C10 -79.00(16)
C5 C4 N9 C10 48.93(15)
O3 C4 N9 C7 50.65(14)
C12 C4 N9 C7 168.70(13)
C5 C4 N9 C7 -63.36(13)
C11 C10 N9 C4 -23.10(17)
C11 C10 N9 C7 76.82(17)
C1 C7 N9 C4 -52.32(14)
C8 C7 N9 C4 -176.11(16)
C6 C7 N9 C4 52.30(15)
C1 C7 N9 C10 -158.37(13)
C8 C7 N9 C10 77.83(19)
C6 C7 N9 C10 -53.76(17)
O2 C1 O3 C4 178.16(18)
C7 C1 O3 C4 -5.99(18)
N9 C4 O3 C1 -29.16(16)
C12 C4 O3 C1 -153.05(14)
C5 C4 O3 C1 73.77(17)
