#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/77/4027792.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_4027792
loop_
_publ_author_name
'Ingrid-Suzy Tamgho'
'James T. Engle'
'Christopher J. Ziegler'
_publ_section_title
;
 Phthalocrowns: Isoindoline-Crown Ether Macrocycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11372
_journal_page_last               11376
_journal_paper_doi               10.1021/jo302227z
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C14 H17 N3 O2'
_chemical_formula_weight         259.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9063(3)
_cell_length_b                   10.3310(3)
_cell_length_c                   13.8954(4)
_cell_measurement_reflns_used    4661
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.42
_cell_measurement_theta_min      4.97
_cell_volume                     1278.53(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4825
_diffrn_reflns_theta_full        66.42
_diffrn_reflns_theta_max         66.42
_diffrn_reflns_theta_min         5.34
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  0.8819
_exptl_absorpt_correction_T_min  0.8423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; [Sheldrick, G. M. (2004)]'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0257
_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)+(0.0564P)²+0.1964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0737
_reflns_number_gt                2030
_reflns_number_total             2046
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302227z_si_003.cif
_cod_data_source_block           3_orthorhombic
_cod_database_code               4027792
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
O1 O 0.17921(10) 0.08632(9) 0.95282(6) 0.0249(2) Uani 1 1 d .
O2 O 0.11422(10) 0.04750(9) 0.75268(6) 0.0245(2) Uani 1 1 d .
N1 N 0.09738(12) 0.37155(11) 0.95780(8) 0.0228(3) Uani 1 1 d .
N2 N 0.12605(12) 0.30441(11) 0.79245(7) 0.0217(2) Uani 1 1 d .
H2 H 0.0657 0.2370 0.7919 0.026 Uiso 1 1 calc R
N3 N 0.22019(12) 0.29284(11) 0.63025(8) 0.0242(3) Uani 1 1 d .
C5 C 0.43971(15) 0.65332(14) 0.74397(10) 0.0266(3) Uani 1 1 d .
H5 H 0.5059 0.7111 0.7119 0.032 Uiso 1 1 calc R
C6 C 0.38068(15) 0.54830(13) 0.69369(9) 0.0248(3) Uani 1 1 d .
H6 H 0.4039 0.5341 0.6278 0.030 Uiso 1 1 calc R
C7 C 0.28644(14) 0.46517(12) 0.74400(9) 0.0217(3) Uani 1 1 d .
C2 C 0.24954(15) 0.48802(13) 0.83997(9) 0.0219(3) Uani 1 1 d .
C1 C 0.14936(13) 0.38294(12) 0.87294(9) 0.0213(3) Uani 1 1 d .
C14 C -0.00073(15) 0.26130(14) 0.97996(9) 0.0253(3) Uani 1 1 d .
H14A H -0.0506 0.2314 0.9203 0.030 Uiso 1 1 calc R
H14B H -0.0796 0.2889 1.0258 0.030 Uiso 1 1 calc R
C13 C 0.08900(15) 0.15054(14) 1.02352(10) 0.0257(3) Uani 1 1 d .
H13A H 0.1547 0.1847 1.0751 0.031 Uiso 1 1 calc R
H13B H 0.0192 0.0873 1.0529 0.031 Uiso 1 1 calc R
C12 C 0.11052(15) -0.02628(13) 0.91293(10) 0.0271(3) Uani 1 1 d .
H12A H 0.0006 -0.0137 0.9084 0.033 Uiso 1 1 calc R
H12B H 0.1300 -0.1021 0.9547 0.033 Uiso 1 1 calc R
C11 C 0.17508(16) -0.04917(13) 0.81470(10) 0.0272(3) Uani 1 1 d .
H11A H 0.2859 -0.0426 0.8166 0.033 Uiso 1 1 calc R
H11B H 0.1476 -0.1366 0.7914 0.033 Uiso 1 1 calc R
C8 C 0.20927(14) 0.34505(13) 0.71313(9) 0.0219(3) Uani 1 1 d .
C9 C 0.13056(14) 0.17655(13) 0.60974(9) 0.0253(3) Uani 1 1 d .
H9A H 0.1315 0.1616 0.5394 0.030 Uiso 1 1 calc R
H9B H 0.0253 0.1939 0.6287 0.030 Uiso 1 1 calc R
C10 C 0.18165(16) 0.05297(14) 0.65938(10) 0.0260(3) Uani 1 1 d .
H10A H 0.1511 -0.0233 0.6210 0.031 Uiso 1 1 calc R
H10B H 0.2924 0.0524 0.6654 0.031 Uiso 1 1 calc R
C3 C 0.30593(14) 0.59448(12) 0.88965(9) 0.0230(3) Uani 1 1 d .
H3 H 0.2787 0.6110 0.9546 0.028 Uiso 1 1 calc R
C4 C 0.40372(14) 0.67550(13) 0.84029(10) 0.0252(3) Uani 1 1 d .
H4 H 0.4469 0.7474 0.8727 0.030 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C12 O1 C13 113.81(10)
C11 O2 C10 114.58(10)
C1 N1 C14 118.87(11)
C8 N2 C1 112.29(10)
C8 N2 H2 123.9
C1 N2 H2 123.9
C8 N3 C9 118.64(11)
C6 C5 C4 121.48(13)
C6 C5 H5 119.3
C4 C5 H5 119.3
C7 C6 C5 117.19(12)
C7 C6 H6 121.4
C5 C6 H6 121.4
C6 C7 C2 121.28(13)
C6 C7 C8 130.70(12)
C2 C7 C8 108.02(11)
C3 C2 C7 121.55(13)
C3 C2 C1 130.11(12)
C7 C2 C1 108.34(11)
N1 C1 N2 129.35(12)
N1 C1 C2 125.10(12)
N2 C1 C2 105.55(10)
N1 C14 C13 110.75(10)
N1 C14 H14A 109.5
C13 C14 H14A 109.5
N1 C14 H14B 109.5
C13 C14 H14B 109.5
H14A C14 H14B 108.1
O1 C13 C14 111.73(11)
O1 C13 H13A 109.3
C14 C13 H13A 109.3
O1 C13 H13B 109.3
C14 C13 H13B 109.3
H13A C13 H13B 107.9
O1 C12 C11 108.53(11)
O1 C12 H12A 110.0
C11 C12 H12A 110.0
O1 C12 H12B 110.0
C11 C12 H12B 110.0
H12A C12 H12B 108.4
O2 C11 C12 107.08(11)
O2 C11 H11A 110.3
C12 C11 H11A 110.3
O2 C11 H11B 110.3
C12 C11 H11B 110.3
H11A C11 H11B 108.6
N3 C8 N2 128.86(12)
N3 C8 C7 125.46(12)
N2 C8 C7 105.67(11)
N3 C9 C10 115.82(10)
N3 C9 H9A 108.3
C10 C9 H9A 108.3
N3 C9 H9B 108.3
C10 C9 H9B 108.3
H9A C9 H9B 107.4
O2 C10 C9 108.59(10)
O2 C10 H10A 110.0
C9 C10 H10A 110.0
O2 C10 H10B 110.0
C9 C10 H10B 110.0
H10A C10 H10B 108.4
C4 C3 C2 117.22(12)
C4 C3 H3 121.4
C2 C3 H3 121.4
C3 C4 C5 121.25(13)
C3 C4 H4 119.4
C5 C4 H4 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C12 1.4264(16)
O1 C13 1.4321(17)
O2 C11 1.4262(16)
O2 C10 1.4300(16)
N1 C1 1.2721(17)
N1 C14 1.4682(17)
N2 C8 1.3930(16)
N2 C1 1.3973(16)
N2 H2 0.8800
N3 C8 1.2754(18)
N3 C9 1.4703(17)
C5 C6 1.3934(19)
C5 C4 1.395(2)
C5 H5 0.9500
C6 C7 1.3895(19)
C6 H6 0.9500
C7 C2 1.3936(18)
C7 C8 1.4820(19)
C2 C3 1.3923(19)
C2 C1 1.4780(18)
C14 C13 1.521(2)
C14 H14A 0.9900
C14 H14B 0.9900
C13 H13A 0.9900
C13 H13B 0.9900
C12 C11 1.4999(19)
C12 H12A 0.9900
C12 H12B 0.9900
C11 H11A 0.9900
C11 H11B 0.9900
C9 C10 1.5208(19)
C9 H9A 0.9900
C9 H9B 0.9900
C10 H10A 0.9900
C10 H10B 0.9900
C3 C4 1.3891(19)
C3 H3 0.9500
C4 H4 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659585
