#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/69/1506937.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_1506937
loop_
_publ_author_name
'Muthyala, Rajeev S.'
'Subramaniam, Gopal'
'Todaro, Louis'
_publ_section_title
;
 The use of squaric acid as a scaffold for cofacial phenyl rings.
;
_journal_issue                   25
_journal_name_full               'Organic letters'
_journal_page_first              4663
_journal_page_last               4665
_journal_paper_doi               10.1021/ol048139s
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 92.82(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4230(15)
_cell_length_b                   14.598(3)
_cell_length_c                   13.890(3)
_cell_measurement_temperature    295(2)
_cell_volume                     1503.3(5)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_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      295(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'ω 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  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0599
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5690
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.36
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9505
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1277
_refine_ls_R_factor_gt           0.0698
_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)+(0.0635P)²+0.4758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1666
_reflns_number_gt                2043
_reflns_number_total             3414
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol048139ssi20040914_034901.cif
_cod_data_source_block           x1498r
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1506937
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
O1 O -0.0134(3) 0.24937(15) 0.50624(14) 0.0768(6) Uani 1 1 d .
O2 O 0.1316(2) 0.44611(14) 0.58906(12) 0.0670(6) Uani 1 1 d .
N5 N 0.2093(2) 0.27972(13) 0.31189(14) 0.0486(5) Uani 1 1 d .
N6 N 0.2922(2) 0.49339(13) 0.38056(13) 0.0445(5) Uani 1 1 d .
C1 C 0.0772(3) 0.31171(18) 0.47653(16) 0.0500(6) Uani 1 1 d .
C2 C 0.1366(3) 0.40440(18) 0.51343(17) 0.0485(6) Uani 1 1 d .
C3 C 0.2143(3) 0.42056(15) 0.41942(15) 0.0397(5) Uani 1 1 d .
C4 C 0.1730(3) 0.33041(16) 0.38894(15) 0.0412(5) Uani 1 1 d .
C6 C 0.1074(4) 0.19498(19) 0.2921(2) 0.0716(8) Uani 1 1 d .
H6A H 0.1877 0.1435 0.2974 0.107 Uiso 1 1 calc R
H6B H 0.0526 0.1974 0.2281 0.107 Uiso 1 1 calc R
H6C H 0.0154 0.1887 0.3378 0.107 Uiso 1 1 calc R
C7 C 0.3353(4) 0.57359(18) 0.44108(18) 0.0587(7) Uani 1 1 d .
H7A H 0.2579 0.6236 0.4215 0.088 Uiso 1 1 calc R
H7B H 0.4588 0.5908 0.4341 0.088 Uiso 1 1 calc R
H7C H 0.3174 0.5588 0.5073 0.088 Uiso 1 1 calc R
C11 C 0.3726(3) 0.29488(16) 0.26316(16) 0.0456(6) Uani 1 1 d .
C12 C 0.5295(3) 0.31467(18) 0.31573(18) 0.0558(7) Uani 1 1 d .
H12A H 0.5294 0.3187 0.3825 0.067 Uiso 1 1 calc R
C13 C 0.6866(4) 0.3286(2) 0.2692(2) 0.0744(9) Uani 1 1 d .
H13A H 0.7921 0.3428 0.3049 0.089 Uiso 1 1 calc R
C14 C 0.6896(4) 0.3218(2) 0.1721(3) 0.0792(9) Uani 1 1 d .
H14A H 0.7968 0.3308 0.1415 0.095 Uiso 1 1 calc R
C15 C 0.5344(5) 0.3016(2) 0.1190(2) 0.0753(9) Uani 1 1 d .
H15A H 0.5367 0.2969 0.0523 0.090 Uiso 1 1 calc R
C16 C 0.3732(4) 0.28821(19) 0.16412(18) 0.0623(7) Uani 1 1 d .
H16A H 0.2675 0.2749 0.1281 0.075 Uiso 1 1 calc R
C21 C 0.2893(3) 0.50620(16) 0.27852(16) 0.0443(6) Uani 1 1 d .
C22 C 0.4372(4) 0.5420(2) 0.23613(19) 0.0672(8) Uani 1 1 d .
H22A H 0.5406 0.5568 0.2733 0.081 Uiso 1 1 calc R
C23 C 0.4304(5) 0.5556(2) 0.1377(2) 0.0818(9) Uani 1 1 d .
H23A H 0.5294 0.5808 0.1088 0.098 Uiso 1 1 calc R
C24 C 0.2803(5) 0.5327(2) 0.0824(2) 0.0815(9) Uani 1 1 d .
H24A H 0.2779 0.5414 0.0161 0.098 Uiso 1 1 calc R
C25 C 0.1332(4) 0.4970(2) 0.1248(2) 0.0739(8) Uani 1 1 d .
H25A H 0.0310 0.4811 0.0871 0.089 Uiso 1 1 calc R
C26 C 0.1363(3) 0.48450(19) 0.22323(18) 0.0564(7) Uani 1 1 d .
H26A H 0.0354 0.4615 0.2522 0.068 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
C4 N5 C11 119.96(19)
C4 N5 C6 119.6(2)
C11 N5 C6 118.74(19)
C3 N6 C21 121.29(18)
C3 N6 C7 119.32(18)
C21 N6 C7 117.13(19)
O1 C1 C4 136.1(2)
O1 C1 C2 135.6(2)
C4 C1 C2 88.23(18)
O2 C2 C3 135.7(2)
O2 C2 C1 136.3(2)
C3 C2 C1 87.89(18)
N6 C3 C4 135.42(19)
N6 C3 C2 133.0(2)
C4 C3 C2 91.59(18)
N5 C4 C3 134.9(2)
N5 C4 C1 133.3(2)
C3 C4 C1 91.83(18)
C12 C11 C16 120.0(2)
C12 C11 N5 119.7(2)
C16 C11 N5 120.3(2)
C11 C12 C13 119.8(2)
C14 C13 C12 120.9(3)
C13 C14 C15 119.8(3)
C14 C15 C16 120.5(3)
C11 C16 C15 119.0(3)
C22 C21 C26 120.2(2)
C22 C21 N6 120.1(2)
C26 C21 N6 119.7(2)
C21 C22 C23 119.3(3)
C24 C23 C22 120.8(3)
C23 C24 C25 119.9(3)
C24 C25 C26 120.1(3)
C21 C26 C25 119.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.216(3)
O2 C2 1.216(3)
N5 C4 1.339(3)
N5 C11 1.434(3)
N5 C6 1.469(3)
N6 C3 1.336(3)
N6 C21 1.429(3)
N6 C7 1.467(3)
C1 C4 1.465(3)
C1 C2 1.505(4)
C2 C3 1.472(3)
C3 C4 1.411(3)
C11 C12 1.374(3)
C11 C16 1.379(3)
C12 C13 1.376(4)
C13 C14 1.354(4)
C14 C15 1.369(4)
C15 C16 1.392(4)
C21 C22 1.374(3)
C21 C26 1.376(3)
C22 C23 1.380(4)
C23 C24 1.363(4)
C24 C25 1.369(4)
C25 C26 1.378(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21157213
