#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/05/7150531.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_7150531
loop_
_publ_author_name
'Garcia-Garibay, Miguel A'
'Dang, Hung'
_publ_section_title
;
 Photochemical generation, intramolecular reactions, and spectroscopic
 detection of oxonium ylide and carbene intermediates in a crystalline
 ortho-(1,3-dioxolan-2-yl)-diaryldiazomethane.
;
_journal_issue                   6
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1106
_journal_page_last               1114
_journal_paper_doi               10.1039/b814387k
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C22 H18 N2 O2'
_chemical_formula_sum            'C22 H18 N2 O2'
_chemical_formula_weight         342.38
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                93.98(1)
_cell_angle_beta                 93.60(1)
_cell_angle_gamma                90.25(2)
_cell_formula_units_Z            2
_cell_length_a                   6.074(1)
_cell_length_b                   11.401(1)
_cell_length_c                   12.309(2)
_cell_measurement_reflns_used    4089
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      2.86
_cell_volume                     848.6(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.917
_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  0.0138
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5564
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_correction_T_min  0.9451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Bruker)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3874
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0398
_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)+(0.0737P)²+0.0244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1185
_reflns_number_gt                3189
_reflns_number_total             3874
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b814387k.txt
_cod_data_source_block           gg230s
_cod_database_code               7150531
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.50043(13) 0.65755(7) -0.02803(7) 0.0241(2) Uani 1 1 d . . .
O2 O 0.23415(13) 0.75201(7) 0.06296(7) 0.0268(2) Uani 1 1 d . . .
N1 N 0.49521(16) 0.73414(8) 0.35758(8) 0.0207(2) Uani 1 1 d . . .
N2 N 0.34822(18) 0.75642(9) 0.40791(9) 0.0295(3) Uani 1 1 d . . .
C1 C 1.31745(19) 0.24980(10) 0.26927(10) 0.0238(3) Uani 1 1 d . . .
H1 H 1.3426 0.2983 0.2115 0.029 Uiso 1 1 calc R . .
C2 C 1.4391(2) 0.14766(11) 0.27916(11) 0.0263(3) Uani 1 1 d . . .
H2 H 1.5485 0.1281 0.2293 0.032 Uiso 1 1 calc R . .
C3 C 1.4017(2) 0.07412(11) 0.36152(10) 0.0268(3) Uani 1 1 d . . .
H3 H 1.4847 0.0043 0.3682 0.032 Uiso 1 1 calc R . .
C4 C 1.2421(2) 0.10379(11) 0.43361(10) 0.0262(3) Uani 1 1 d . . .
H4 H 1.2137 0.0531 0.4893 0.031 Uiso 1 1 calc R . .
C5 C 1.1225(2) 0.20705(10) 0.42568(10) 0.0232(3) Uani 1 1 d . . .
H5 H 1.0153 0.2267 0.4767 0.028 Uiso 1 1 calc R . .
C6 C 1.15872(19) 0.28242(10) 0.34293(9) 0.0199(2) Uani 1 1 d . . .
C7 C 1.03239(19) 0.39341(10) 0.33370(9) 0.0193(2) Uani 1 1 d . . .
C8 C 0.83235(19) 0.41069(10) 0.38287(10) 0.0222(3) Uani 1 1 d . . .
H8 H 0.7765 0.3503 0.4233 0.027 Uiso 1 1 calc R . .
C9 C 0.71356(19) 0.51362(10) 0.37416(10) 0.0220(3) Uani 1 1 d . . .
H9 H 0.5796 0.5232 0.4096 0.026 Uiso 1 1 calc R . .
C10 C 0.78923(19) 0.60390(9) 0.31352(9) 0.0187(2) Uani 1 1 d . . .
C11 C 0.98811(19) 0.58690(10) 0.26348(9) 0.0209(2) Uani 1 1 d . . .
H11 H 1.0425 0.6464 0.2217 0.025 Uiso 1 1 calc R . .
C12 C 1.10685(19) 0.48441(10) 0.27408(10) 0.0217(2) Uani 1 1 d . . .
H12 H 1.2424 0.4756 0.2400 0.026 Uiso 1 1 calc R . .
C13 C 0.66577(19) 0.71211(10) 0.29975(9) 0.0195(2) Uani 1 1 d . . .
C14 C 0.71724(18) 0.80258(9) 0.22230(9) 0.0184(2) Uani 1 1 d . . .
C15 C 0.87052(19) 0.89208(10) 0.25585(10) 0.0222(3) Uani 1 1 d . . .
H15 H 0.9453 0.8928 0.3260 0.027 Uiso 1 1 calc R . .
C16 C 0.91366(19) 0.97975(10) 0.18703(10) 0.0238(3) Uani 1 1 d . . .
H16 H 1.0173 1.0404 0.2101 0.029 Uiso 1 1 calc R . .
C17 C 0.80450(19) 0.97841(10) 0.08412(10) 0.0228(3) Uani 1 1 d . . .
H17 H 0.8304 1.0396 0.0378 0.027 Uiso 1 1 calc R . .
C18 C 0.65846(19) 0.88831(10) 0.04920(10) 0.0213(3) Uani 1 1 d . . .
H18 H 0.5885 0.8865 -0.0221 0.026 Uiso 1 1 calc R . .
C19 C 0.61260(18) 0.79958(9) 0.11785(9) 0.0189(2) Uani 1 1 d . . .
C20 C 0.44993(19) 0.70484(10) 0.07642(9) 0.0205(2) Uani 1 1 d . . .
H20 H 0.4507 0.6412 0.1284 0.025 Uiso 1 1 calc R . .
C21 C 0.1236(2) 0.68733(12) -0.02911(12) 0.0340(3) Uani 1 1 d . . .
H21A H 0.0702 0.7409 -0.0848 0.041 Uiso 1 1 calc R . .
H21B H -0.0035 0.6424 -0.0063 0.041 Uiso 1 1 calc R . .
C22 C 0.2970(2) 0.60515(11) -0.07337(11) 0.0283(3) Uani 1 1 d . . .
H22A H 0.2783 0.5249 -0.0491 0.034 Uiso 1 1 calc R . .
H22B H 0.2902 0.6012 -0.1541 0.034 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O1 C22 104.16(9) . . ?
C20 O2 C21 107.13(9) . . ?
N2 N1 C13 178.17(11) . . ?
C2 C1 C6 121.15(11) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C3 C2 C1 120.40(11) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.18(11) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.83(11) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.66(11) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.76(10) . . ?
C1 C6 C7 121.02(10) . . ?
C5 C6 C7 121.22(10) . . ?
C8 C7 C12 117.03(10) . . ?
C8 C7 C6 121.47(10) . . ?
C12 C7 C6 121.49(10) . . ?
C9 C8 C7 121.73(11) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 120.69(11) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 117.89(10) . . ?
C11 C10 C13 119.74(10) . . ?
C9 C10 C13 122.35(10) . . ?
C12 C11 C10 120.87(10) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C7 121.78(11) . . ?
C11 C12 H12 119.1 . . ?
C7 C12 H12 119.1 . . ?
N1 C13 C10 119.35(10) . . ?
N1 C13 C14 115.69(9) . . ?
C10 C13 C14 124.97(10) . . ?
C19 C14 C15 119.76(10) . . ?
C19 C14 C13 120.85(10) . . ?
C15 C14 C13 119.39(10) . . ?
C16 C15 C14 120.33(11) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.77(11) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.16(11) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.69(11) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C18 119.23(11) . . ?
C14 C19 C20 122.29(10) . . ?
C18 C19 C20 118.48(10) . . ?
O1 C20 O2 105.70(9) . . ?
O1 C20 C19 110.68(9) . . ?
O2 C20 C19 110.53(9) . . ?
O1 C20 H20 110.0 . . ?
O2 C20 H20 110.0 . . ?
C19 C20 H20 110.0 . . ?
O2 C21 C22 104.70(10) . . ?
O2 C21 H21A 110.8 . . ?
C22 C21 H21A 110.8 . . ?
O2 C21 H21B 110.8 . . ?
C22 C21 H21B 110.8 . . ?
H21A C21 H21B 108.9 . . ?
O1 C22 C21 103.43(10) . . ?
O1 C22 H22A 111.1 . . ?
C21 C22 H22A 111.1 . . ?
O1 C22 H22B 111.1 . . ?
C21 C22 H22B 111.1 . . ?
H22A C22 H22B 109.0 . . ?
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
O1 C20 1.4116(14) . ?
O1 C22 1.4340(14) . ?
O2 C20 1.4233(14) . ?
O2 C21 1.4364(15) . ?
N1 N2 1.1381(14) . ?
N1 C13 1.3089(15) . ?
C1 C2 1.3903(16) . ?
C1 C6 1.3987(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.3885(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3822(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3919(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.4044(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.4901(15) . ?
C7 C8 1.3998(16) . ?
C7 C12 1.4009(16) . ?
C8 C9 1.3872(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.4048(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.3983(16) . ?
C10 C13 1.4609(15) . ?
C11 C12 1.3854(16) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.4973(15) . ?
C14 C19 1.3963(16) . ?
C14 C15 1.4011(16) . ?
C15 C16 1.3887(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.3916(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.3818(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.4002(15) . ?
C18 H18 0.9500 . ?
C19 C20 1.5013(16) . ?
C20 H20 1.0000 . ?
C21 C22 1.5143(18) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.46(19) . . . . ?
C1 C2 C3 C4 -0.08(18) . . . . ?
C2 C3 C4 C5 -1.21(19) . . . . ?
C3 C4 C5 C6 1.12(19) . . . . ?
C2 C1 C6 C5 -1.52(17) . . . . ?
C2 C1 C6 C7 178.52(11) . . . . ?
C4 C5 C6 C1 0.24(18) . . . . ?
C4 C5 C6 C7 -179.80(11) . . . . ?
C1 C6 C7 C8 160.33(11) . . . . ?
C5 C6 C7 C8 -19.63(17) . . . . ?
C1 C6 C7 C12 -18.72(17) . . . . ?
C5 C6 C7 C12 161.33(11) . . . . ?
C12 C7 C8 C9 -0.64(18) . . . . ?
C6 C7 C8 C9 -179.72(11) . . . . ?
C7 C8 C9 C10 1.10(19) . . . . ?
C8 C9 C10 C11 -0.58(17) . . . . ?
C8 C9 C10 C13 178.17(11) . . . . ?
C9 C10 C11 C12 -0.35(17) . . . . ?
C13 C10 C11 C12 -179.14(11) . . . . ?
C10 C11 C12 C7 0.81(18) . . . . ?
C8 C7 C12 C11 -0.31(17) . . . . ?
C6 C7 C12 C11 178.77(11) . . . . ?
C11 C10 C13 N1 -171.42(11) . . . . ?
C9 C10 C13 N1 9.85(17) . . . . ?
C11 C10 C13 C14 9.12(17) . . . . ?
C9 C10 C13 C14 -169.61(11) . . . . ?
N1 C13 C14 C19 -85.53(13) . . . . ?
C10 C13 C14 C19 93.95(14) . . . . ?
N1 C13 C14 C15 93.70(13) . . . . ?
C10 C13 C14 C15 -86.82(14) . . . . ?
C19 C14 C15 C16 2.01(17) . . . . ?
C13 C14 C15 C16 -177.23(10) . . . . ?
C14 C15 C16 C17 -0.20(17) . . . . ?
C15 C16 C17 C18 -1.89(17) . . . . ?
C16 C17 C18 C19 2.17(17) . . . . ?
C15 C14 C19 C18 -1.73(16) . . . . ?
C13 C14 C19 C18 177.50(10) . . . . ?
C15 C14 C19 C20 178.90(10) . . . . ?
C13 C14 C19 C20 -1.87(16) . . . . ?
C17 C18 C19 C14 -0.35(16) . . . . ?
C17 C18 C19 C20 179.05(10) . . . . ?
C22 O1 C20 O2 -38.99(11) . . . . ?
C22 O1 C20 C19 -158.69(9) . . . . ?
C21 O2 C20 O1 26.52(12) . . . . ?
C21 O2 C20 C19 146.31(10) . . . . ?
C14 C19 C20 O1 -131.15(11) . . . . ?
C18 C19 C20 O1 49.48(13) . . . . ?
C14 C19 C20 O2 112.10(11) . . . . ?
C18 C19 C20 O2 -67.27(13) . . . . ?
C20 O2 C21 C22 -4.12(13) . . . . ?
C20 O1 C22 C21 35.31(12) . . . . ?
O2 C21 C22 O1 -19.07(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25942187
