#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:50:45 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180237 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/23/7112341.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_7112341
loop_
_publ_author_name
'do Pim, Walace D.'
'Oliveira, Willian X. C.'
'Ribeiro, Marcos A.'
'de Faria, Érica N'
'Teixeira, Ivo F.'
'Stumpf, Humberto O.'
'Lago, Rochel M.'
'Pereira, Cynthia L. M.'
'Pinheiro, Carlos B.'
'Figueiredo, Jr, João C D'
'Nunes, Wallace C.'
'de Souza, Patterson P.'
'Pedroso, Emerson F.'
'Castellano, María'
'Cano, Joan'
'Julve, Miguel'
_publ_section_title
;
 A pH-triggered bistable copper(II) metallacycle as a reversible emulsion
 switch for biphasic processes.
;
_journal_issue                   92
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10778
_journal_page_last               10780
_journal_paper_doi               10.1039/c3cc46242k
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C11 H12 N O3'
_chemical_formula_weight         206.22
_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
_cell_angle_alpha                90
_cell_angle_beta                 93.502(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6560(2)
_cell_length_b                   9.1479(2)
_cell_length_c                   16.3406(4)
_cell_measurement_reflns_used    6741
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.4672
_cell_measurement_theta_min      3.2331
_cell_volume                     993.10(4)
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
;
_computing_data_collection
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.4186
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0060634
_diffrn_orient_matrix_UB_12      0.0323697
_diffrn_orient_matrix_UB_13      -0.0395423
_diffrn_orient_matrix_UB_21      0.02409
_diffrn_orient_matrix_UB_22      0.0690292
_diffrn_orient_matrix_UB_23      0.0177544
_diffrn_orient_matrix_UB_31      0.1037964
_diffrn_orient_matrix_UB_32      -0.0141319
_diffrn_orient_matrix_UB_33      -0.0036916
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12200
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.35
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
        (compiled Jan  5 2010,16:28:46)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.5761
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.1204
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.94
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.94
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0327
_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)+(0.0750P)²+0.1177P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.103
_reflns_number_gt                1654
_reflns_number_total             2039
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc46242k.txt
_cod_data_source_block           edpba_f
_cod_depositor_comments
'Adding full bibliography for 7112340--7112342.cif.'
_cod_database_code               7112341
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
_atom_site_refinement_flags
O2 O 0.30895(15) 0.09833(10) 0.53717(6) 0.0372(3) Uani 1 1 d .
O1 O 0.31811(13) -0.11352(9) 0.60725(5) 0.0247(2) Uani 1 1 d .
N1 N 0.18987(14) -0.26575(11) 0.48240(6) 0.0203(2) Uani 1 1 d .
O3 O 0.15137(14) -0.06099(11) 0.40201(6) 0.0376(3) Uani 1 1 d .
C9 C 0.39927(15) -0.53319(11) 0.51232(7) 0.0167(3) Uani 1 1 d .
H9A H 0.4189 -0.6381 0.5252 0.025 Uiso 1 1 calc R
H9B H 0.3568 -0.4837 0.5623 0.025 Uiso 1 1 calc R
C4 C 0.23584(16) -0.51705(12) 0.44460(6) 0.0173(3) Uani 1 1 d .
C8 C -0.00067(18) -0.36643(14) 0.36236(7) 0.0238(3) Uani 1 1 d .
H8 H -0.0651 -0.275 0.3522 0.029 Uiso 1 1 calc R
C5 C 0.18154(17) -0.63516(13) 0.39452(7) 0.0214(3) Uani 1 1 d .
H5 H 0.2407 -0.7281 0.4057 0.026 Uiso 1 1 calc R
C2 C 0.19792(17) -0.12148(13) 0.46678(8) 0.0230(3) Uani 1 1 d .
C3 C 0.14039(17) -0.38253(13) 0.42806(7) 0.0184(3) Uani 1 1 d .
C10 C 0.3979(2) -0.03953(15) 0.68155(8) 0.0329(3) Uani 1 1 d .
H10A H 0.296 0.0281 0.7019 0.039 Uiso 1 1 calc R
H10B H 0.5193 0.0176 0.67 0.039 Uiso 1 1 calc R
C11 C 0.4499(2) -0.15540(16) 0.74427(8) 0.0335(3) Uani 1 1 d .
H11A H 0.3295 -0.213 0.7539 0.05 Uiso 1 1 calc R
H11B H 0.5001 -0.1093 0.7956 0.05 Uiso 1 1 calc R
H11C H 0.554 -0.2196 0.7242 0.05 Uiso 1 1 calc R
C7 C -0.04633(17) -0.48476(16) 0.31185(7) 0.0280(3) Uani 1 1 d .
H7 H -0.1388 -0.4736 0.2657 0.034 Uiso 1 1 calc R
C6 C 0.04236(19) -0.61946(15) 0.32838(7) 0.0267(3) Uani 1 1 d .
H6 H 0.0078 -0.7011 0.2944 0.032 Uiso 1 1 calc R
C1 C 0.27975(17) -0.03078(13) 0.54091(8) 0.0243(3) Uani 1 1 d .
H1 H 0.229(2) -0.2862(17) 0.5333(10) 0.036 Uiso 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
9 -2 -4 0.2676
0 0 4 0.0676
0 -13 -4 0.0716
0 -3 0 0.0923
0 3 -22 0.0923
0 -3 -1 0.0585
0 13 5 0.0595
-2 0 1 0.2796
1 3 1 0.1325
1 -4 -2 0.0931
-1 -3 -1 0.0914
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
C1 O1 C10 117.01(10) . .
C2 N1 C3 129.18(10) . .
C2 N1 H1 112.2(10) . .
C3 N1 H1 118.5(10) . .
C4 C9 C9 111.57(11) . 3_646
C4 C9 H9A 109.3 . .
C9 C9 H9A 109.3 3_646 .
C4 C9 H9B 109.3 . .
C9 C9 H9B 109.3 3_646 .
H9A C9 H9B 108 . .
C5 C4 C3 118.03(10) . .
C5 C4 C9 120.33(10) . .
C3 C4 C9 121.59(10) . .
C7 C8 C3 119.42(11) . .
C7 C8 H8 120.3 . .
C3 C8 H8 120.3 . .
C6 C5 C4 121.03(11) . .
C6 C5 H5 119.5 . .
C4 C5 H5 119.5 . .
O3 C2 N1 126.84(12) . .
O3 C2 C1 119.85(11) . .
N1 C2 C1 113.29(10) . .
C8 C3 C4 121.20(11) . .
C8 C3 N1 121.66(11) . .
C4 C3 N1 117.12(10) . .
O1 C10 C11 107.29(10) . .
O1 C10 H10A 110.3 . .
C11 C10 H10A 110.3 . .
O1 C10 H10B 110.3 . .
C11 C10 H10B 110.3 . .
H10A C10 H10B 108.5 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C8 C7 C6 120.25(11) . .
C8 C7 H7 119.9 . .
C6 C7 H7 119.9 . .
C7 C6 C5 120.01(11) . .
C7 C6 H6 120 . .
C5 C6 H6 120 . .
O2 C1 O1 125.22(12) . .
O2 C1 C2 122.77(12) . .
O1 C1 C2 111.99(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C1 1.1991(15) .
O1 C1 1.3340(15) .
O1 C10 1.4614(15) .
N1 C2 1.3458(15) .
N1 C3 1.4151(15) .
N1 H1 0.876(15) .
O3 C2 1.2174(15) .
C9 C4 1.5109(15) .
C9 C9 1.548(2) 3_646
C9 H9A 0.99 .
C9 H9B 0.99 .
C4 C5 1.3898(16) .
C4 C3 1.4035(16) .
C8 C7 1.3838(18) .
C8 C3 1.3901(16) .
C8 H8 0.95 .
C5 C6 1.3872(17) .
C5 H5 0.95 .
C2 C1 1.5401(18) .
C10 C11 1.500(2) .
C10 H10A 0.99 .
C10 H10B 0.99 .
C11 H11A 0.98 .
C11 H11B 0.98 .
C11 H11C 0.98 .
C7 C6 1.3858(19) .
C7 H7 0.95 .
C6 H6 0.95 .
