#------------------------------------------------------------------------------
#$Date: 2019-11-25 04:41:28 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240036 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/92/4129286.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_4129286
loop_
_publ_author_name
'Do, Jean-Louis'
'Mottillo, Cristina'
'Tan, Davin'
'Štrukil, Vjekoslav'
'Friščić, Tomislav'
_publ_section_title
;
 Mechanochemical ruthenium-catalyzed olefin metathesis.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2476
_journal_page_last               2479
_journal_paper_doi               10.1021/jacs.5b00151
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         C13H13N3O5
_chemical_formula_sum            'C13 H13 N3 O5'
_chemical_formula_weight         291.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90.5260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3929(6)
_cell_length_b                   6.9352(5)
_cell_length_c                   21.3856(14)
_cell_measurement_temperature    296(2)
_cell_volume                     1393.03(16)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14651
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.905
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0463P)²+0.2213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.1032
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2139
_reflns_number_total             2850
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b00151_si_002.cif
_cod_data_source_block           5a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4129286
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.42385(12) 0.64009(17) 0.93731(5) 0.0776(4) Uani 1 1 d . U
N1 N 0.55936(12) 0.48713(17) 0.86604(5) 0.0540(3) Uani 1 1 d . U
O2 O 0.33394(14) -0.06108(18) 1.04544(5) 0.0778(3) Uani 1 1 d . U
O5 O -0.08514(14) 0.0733(2) 0.82593(7) 0.0882(4) Uani 1 1 d . U
O3 O 0.13687(14) -0.1819(2) 1.01079(6) 0.0893(4) Uani 1 1 d . U
N2 N 0.23620(15) -0.06893(19) 1.00762(6) 0.0628(3) Uani 1 1 d . U
N3 N 0.01630(16) 0.1768(2) 0.81586(7) 0.0718(4) Uani 1 1 d . U
C10 C 0.23684(14) 0.0684(2) 0.95507(6) 0.0516(3) Uani 1 1 d . U
C7 C 0.44639(16) 0.5006(2) 0.90341(6) 0.0550(3) Uani 1 1 d . U
C8 C 0.34080(15) 0.3369(2) 0.90328(6) 0.0517(3) Uani 1 1 d . U
C12 C 0.13100(15) 0.1860(2) 0.86325(6) 0.0552(4) Uani 1 1 d . U
C9 C 0.34199(14) 0.2063(2) 0.95251(6) 0.0530(3) Uani 1 1 d . U
H9 H 0.4126 0.2119 0.9832 0.064 Uiso 1 1 calc R U
C11 C 0.12862(15) 0.0552(2) 0.91141(7) 0.0547(4) Uani 1 1 d . U
H11 H 0.0575 -0.0376 0.9144 0.066 Uiso 1 1 calc R U
C13 C 0.23476(16) 0.3258(2) 0.85781(7) 0.0572(4) Uani 1 1 d . U
H13 H 0.2336 0.4111 0.8243 0.069 Uiso 1 1 calc R U
C6 C 0.59171(16) 0.3197(2) 0.82695(6) 0.0559(4) Uani 1 1 d . U
H6A H 0.5330 0.2119 0.8398 0.067 Uiso 1 1 calc R U
H6B H 0.6906 0.2836 0.8333 0.067 Uiso 1 1 calc R U
O4 O 0.02873(17) 0.2746(3) 0.76933(7) 0.1171(6) Uani 1 1 d . U
C3 C 0.66637(16) 0.6408(2) 0.86710(7) 0.0608(4) Uani 1 1 d . U
H3A H 0.6236 0.7586 0.8826 0.073 Uiso 1 1 calc R U
H3B H 0.6990 0.6646 0.8249 0.073 Uiso 1 1 calc R U
C5 C 0.56616(17) 0.3585(2) 0.75895(7) 0.0610(4) Uani 1 1 d . U
H5 H 0.4750 0.3959 0.7467 0.073 Uiso 1 1 calc R U
C2 C 0.79040(17) 0.5877(2) 0.90775(8) 0.0663(4) Uani 1 1 d . U
H2 H 0.7709 0.5394 0.9473 0.080 Uiso 1 1 calc R U
C4 C 0.6618(2) 0.3439(3) 0.71588(8) 0.0751(5) Uani 1 1 d . U
H4A H 0.7541 0.3068 0.7264 0.090 Uiso 1 1 calc R U
H4B H 0.6381 0.3704 0.6744 0.090 Uiso 1 1 calc R U
C1 C 0.9226(2) 0.6034(3) 0.89245(11) 0.0878(6) Uani 1 1 d . U
H1A H 0.9466 0.6510 0.8533 0.105 Uiso 1 1 calc R U
H1B H 0.9937 0.5670 0.9206 0.105 Uiso 1 1 calc R U
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
C7 N1 C6 124.50(12)
C7 N1 C3 119.20(12)
C6 N1 C3 116.09(11)
O2 N2 O3 124.28(14)
O2 N2 C10 117.96(13)
O3 N2 C10 117.75(14)
O4 N3 O5 123.98(16)
O4 N3 C12 117.75(15)
O5 N3 C12 118.27(15)
C9 C10 C11 123.01(13)
C9 C10 N2 119.18(13)
C11 C10 N2 117.78(13)
O1 C7 N1 123.35(14)
O1 C7 C8 118.50(13)
N1 C7 C8 118.15(12)
C13 C8 C9 119.72(13)
C13 C8 C7 120.73(13)
C9 C8 C7 119.28(13)
C11 C12 C13 122.93(14)
C11 C12 N3 118.08(14)
C13 C12 N3 118.99(14)
C10 C9 C8 118.86(13)
C12 C11 C10 116.61(13)
C12 C13 C8 118.86(14)
N1 C6 C5 112.32(12)
N1 C3 C2 111.17(13)
C4 C5 C6 124.78(16)
C1 C2 C3 125.35(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2284(17)
N1 C7 1.3375(18)
N1 C6 1.4644(17)
N1 C3 1.4649(18)
O2 N2 1.2190(17)
O5 N3 1.2138(18)
O3 N2 1.2206(17)
N2 C10 1.4733(18)
N3 O4 1.2108(19)
N3 C12 1.474(2)
C10 C9 1.376(2)
C10 C11 1.377(2)
C7 C8 1.508(2)
C8 C13 1.388(2)
C8 C9 1.3886(19)
C12 C11 1.373(2)
C12 C13 1.381(2)
C6 C5 1.496(2)
C3 C2 1.493(2)
C5 C4 1.297(2)
C2 C1 1.291(2)
