#------------------------------------------------------------------------------
#$Date: 2016-02-14 05:40:26 +0100 (dom 14 de feb de 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/71/4107148.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_4107148
loop_
_publ_author_name
'Matthew J. Kryger'
'Alexander M. Munaretto'
'Jeffrey S. Moore'
_publ_section_title
;
 Structure-Mechanochemical Activity Relationships for Cyclobutane
 Mechanophores
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18992
_journal_page_last               18998
_journal_paper_doi               10.1021/ja2086728
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C9 H11 N O4'
_chemical_formula_sum            'C9 H11 N O4'
_chemical_formula_weight         197.19
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
2008-08-08 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 113.616(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5062(10)
_cell_length_b                   6.2721(5)
_cell_length_c                   13.3644(13)
_cell_measurement_reflns_used    2082
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.74
_cell_measurement_theta_min      3.08
_cell_volume                     960.51(15)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.0-1 (Bruker, 2004)'
_computing_data_reduction
; 
SAINT V7.23A, XPREP V2005/2, SADABS V2007/4 (Bruker, 2005 & 2007) 
;
_computing_molecular_graphics    'SHELXTL V6.12 (Bruker, 2005)'
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  ba41c_14
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10238
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.9708
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       tabular
_exptl_crystal_F_000             416
_exptl_crystal_id                ba41c_14
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (-1 0 3) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0487
_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)+(0.0563P)²+0.7299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1306
_reflns_number_gt                1211
_reflns_number_total             1717
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2086728_si_003.cif
_cod_data_source_block           ba41cas
_cod_original_cell_volume        960.51(14)
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               4107148
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
C1 C 0.2121(2) -0.0258(4) 0.5861(2) 0.0254(6) Uani 1 1 d
C2 C 0.14529(19) -0.1053(4) 0.6521(2) 0.0232(6) Uani 1 1 d
C3 C 0.1014(2) -0.3410(4) 0.6199(3) 0.0306(6) Uani 1 1 d
H3A H 0.029(2) -0.357(5) 0.631(2) 0.037 Uiso 1 1 d
H3B H 0.091(2) -0.377(5) 0.547(3) 0.037 Uiso 1 1 d
C4 C 0.2089(3) -0.4242(4) 0.7151(3) 0.0329(7) Uani 1 1 d
H4A H 0.195(2) -0.531(5) 0.764(2) 0.040 Uiso 1 1 d
H4B H 0.271(2) -0.468(5) 0.697(2) 0.040 Uiso 1 1 d
C5 C 0.2310(2) -0.1988(4) 0.7655(2) 0.0249(6) Uani 1 1 d
H5A H 0.200(2) -0.185(4) 0.815(2) 0.030 Uiso 1 1 d
C6 C 0.3528(2) -0.1154(4) 0.8154(2) 0.0247(6) Uani 1 1 d
C7 C 0.0587(2) 0.0491(4) 0.6560(2) 0.0260(6) Uani 1 1 d
C8 C 0.2512(3) 0.2629(5) 0.4937(3) 0.0410(8) Uani 1 1 d
H8A H 0.229(3) 0.411(6) 0.484(3) 0.061 Uiso 1 1 d
H8B H 0.338(3) 0.244(5) 0.535(3) 0.061 Uiso 1 1 d
H8C H 0.229(3) 0.205(6) 0.430(3) 0.061 Uiso 1 1 d
C9 C 0.4678(3) 0.1998(5) 0.8582(3) 0.0380(8) Uani 1 1 d
H9A H 0.453(3) 0.336(6) 0.846(3) 0.057 Uiso 1 1 d
H9B H 0.512(3) 0.157(5) 0.817(3) 0.057 Uiso 1 1 d
H9C H 0.511(3) 0.164(5) 0.934(3) 0.057 Uiso 1 1 d
N1 N -0.01065(19) 0.1623(4) 0.6601(2) 0.0391(6) Uani 1 1 d
O1 O 0.18611(15) 0.1747(3) 0.55273(15) 0.0300(5) Uani 1 1 d
O2 O 0.28092(16) -0.1346(3) 0.56796(18) 0.0425(6) Uani 1 1 d
O3 O 0.35360(14) 0.0983(3) 0.81360(15) 0.0308(5) Uani 1 1 d
O4 O 0.43882(15) -0.2245(3) 0.85377(16) 0.0381(5) 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 0.0000 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 0.00 0.1900
0.00 -1.00 0.00 0.1600
1.00 0.00 0.00 0.0500
-1.00 0.00 0.00 0.0600
0.00 0.00 1.00 0.0700
0.00 0.00 -1.00 0.0700
-1.00 0.00 -1.00 0.0600
-1.00 0.00 1.00 0.0600
1.00 0.00 -1.00 0.0800
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 C1 O1 124.7(2)
O2 C1 C2 122.5(2)
O1 C1 C2 112.8(2)
C7 C2 C1 112.9(2)
C7 C2 C3 116.6(2)
C1 C2 C3 111.2(2)
C7 C2 C5 115.9(2)
C1 C2 C5 111.08(19)
C3 C2 C5 86.63(18)
C4 C3 C2 89.97(19)
C4 C3 H3A 113.3(17)
C2 C3 H3A 107.2(17)
C4 C3 H3B 119.0(16)
C2 C3 H3B 113.1(18)
H3A C3 H3B 112(2)
C3 C4 C5 89.7(2)
C3 C4 H4A 116.5(16)
C5 C4 H4A 111.9(17)
C3 C4 H4B 114.9(18)
C5 C4 H4B 111.0(18)
H4A C4 H4B 111(2)
C6 C5 C4 119.3(2)
C6 C5 C2 118.6(2)
C4 C5 C2 89.29(19)
C6 C5 H5A 107.9(17)
C4 C5 H5A 110.6(17)
C2 C5 H5A 110.1(17)
O4 C6 O3 124.3(2)
O4 C6 C5 124.8(2)
O3 C6 C5 110.9(2)
N1 C7 C2 177.3(3)
O1 C8 H8A 104(2)
O1 C8 H8B 112(2)
H8A C8 H8B 112(3)
O1 C8 H8C 110(2)
H8A C8 H8C 108(3)
H8B C8 H8C 110(3)
O3 C9 H9A 105(2)
O3 C9 H9B 110.0(19)
H9A C9 H9B 107(3)
O3 C9 H9C 112.0(19)
H9A C9 H9C 114(3)
H9B C9 H9C 109(3)
C1 O1 C8 115.3(2)
C6 O3 C9 116.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.197(3)
C1 O1 1.330(3)
C1 C2 1.521(3)
C2 C7 1.469(3)
C2 C3 1.576(3)
C2 C5 1.577(3)
C3 C4 1.525(4)
C3 H3A 0.98(3)
C3 H3B 0.96(3)
C4 C5 1.542(4)
C4 H4A 1.01(3)
C4 H4B 0.94(3)
C5 C6 1.492(3)
C5 H5A 0.90(3)
C6 O4 1.203(3)
C6 O3 1.341(3)
C7 N1 1.139(3)
C8 O1 1.451(3)
C8 H8A 0.96(4)
C8 H8B 1.01(4)
C8 H8C 0.86(4)
C9 O3 1.455(3)
C9 H9A 0.88(4)
C9 H9B 0.97(4)
C9 H9C 0.96(4)
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
O2 C1 C2 C7 -175.2(2)
O1 C1 C2 C7 5.4(3)
O2 C1 C2 C3 -42.1(3)
O1 C1 C2 C3 138.5(2)
O2 C1 C2 C5 52.6(3)
O1 C1 C2 C5 -126.8(2)
C7 C2 C3 C4 -133.2(2)
C1 C2 C3 C4 95.6(2)
C5 C2 C3 C4 -15.7(2)
C2 C3 C4 C5 16.1(2)
C3 C4 C5 C6 -138.8(3)
C3 C4 C5 C2 -16.0(2)
C7 C2 C5 C6 -103.1(3)
C1 C2 C5 C6 27.5(3)
C3 C2 C5 C6 138.9(2)
C7 C2 C5 C4 133.5(2)
C1 C2 C5 C4 -95.9(2)
C3 C2 C5 C4 15.5(2)
C4 C5 C6 O4 -26.5(4)
C2 C5 C6 O4 -133.3(3)
C4 C5 C6 O3 154.4(2)
C2 C5 C6 O3 47.6(3)
O2 C1 O1 C8 -2.2(4)
C2 C1 O1 C8 177.2(2)
O4 C6 O3 C9 2.2(4)
C5 C6 O3 C9 -178.8(2)
