#------------------------------------------------------------------------------
#$Date: 2017-03-04 15:45:33 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193495 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/54/4125499.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_4125499
loop_
_publ_author_name
'Karak, Suvendu'
'Kandambeth, Sharath'
'Biswal, Bishnu P.'
'Sasmal, Himadri Sekhar'
'Kumar, Sushil'
'Pachfule, Pradip'
'Banerjee, Rahul'
_publ_section_title
;
 Constructing Ultraporous Covalent Organic Frameworks in Seconds via an
 Organic Terracotta Process.
;
_journal_issue                   5
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1856
_journal_page_last               1862
_journal_paper_doi               10.1021/jacs.6b08815
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C14 H18 N2 O2, 2(C7 H7 O3 S)'
_chemical_formula_sum            'C28 H32 N2 O8 S2'
_chemical_formula_weight         588.68
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                90.000(5)
_cell_angle_beta                 101.570(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   21.814(5)
_cell_length_b                   5.665(5)
_cell_length_c                   23.078(5)
_cell_measurement_reflns_used    2467
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.58
_cell_measurement_theta_min      3.98
_cell_volume                     2794(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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     1.54184
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14085
_diffrn_reflns_theta_full        66.58
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         3.91
_exptl_absorpt_coefficient_mu    2.184
_exptl_absorpt_correction_T_max  0.6817
_exptl_absorpt_correction_T_min  0.6222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0655
_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)+(0.0000P)²+22.1807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1301
_reflns_number_gt                1914
_reflns_number_total             2467
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja6b08815_si_002.cif
_cod_data_source_block           PTSA-BD-OMe2
_cod_depositor_comments
'Adding full bibliography for 4125492--4125502.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4125499
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C1 C 0.09159(19) 0.2553(9) 0.28953(18) 0.0312(11) Uani 1 1 d .
H1A H 0.0722 0.1032 0.2821 0.047 Uiso 1 1 calc R
H1B H 0.0598 0.3746 0.2863 0.047 Uiso 1 1 calc R
H1C H 0.1170 0.2580 0.3286 0.047 Uiso 1 1 calc R
C2 C 0.13192(18) 0.3024(7) 0.24492(16) 0.0208(9) Uani 1 1 d .
C3 C 0.16523(18) 0.5107(7) 0.24588(16) 0.0216(9) Uani 1 1 d .
H3 H 0.1627 0.6231 0.2747 0.026 Uiso 1 1 calc R
C4 C 0.20221(17) 0.5552(7) 0.20482(15) 0.0197(8) Uani 1 1 d .
H4 H 0.2242 0.6963 0.2061 0.024 Uiso 1 1 calc R
C5 C 0.20634(17) 0.3878(7) 0.16162(15) 0.0165(8) Uani 1 1 d .
C6 C 0.17476(18) 0.1758(7) 0.16059(16) 0.0202(9) Uani 1 1 d .
H6 H 0.1783 0.0619 0.1324 0.024 Uiso 1 1 calc R
C7 C 0.13770(18) 0.1343(7) 0.20197(16) 0.0206(9) Uani 1 1 d .
H7 H 0.1163 -0.0081 0.2011 0.025 Uiso 1 1 calc R
C8 C 0.12018(17) 0.6547(7) -0.03991(15) 0.0146(8) Uani 1 1 d .
C9 C 0.13499(17) 0.8496(7) -0.00446(16) 0.0190(9) Uani 1 1 d .
H9 H 0.1767 0.8895 0.0093 0.023 Uiso 1 1 calc R
C10 C 0.08844(17) 0.9865(7) 0.01089(16) 0.0214(9) Uani 1 1 d .
H10 H 0.0991 1.1180 0.0349 0.026 Uiso 1 1 calc R
C11 C 0.02558(16) 0.9303(7) -0.00923(15) 0.0166(8) Uani 1 1 d .
C12 C 0.01108(17) 0.7355(7) -0.04674(15) 0.0170(8) Uani 1 1 d .
H12 H -0.0306 0.6983 -0.0619 0.020 Uiso 1 1 calc R
C13 C 0.05824(17) 0.5968(6) -0.06168(15) 0.0154(8) Uani 1 1 d .
C14 C -0.01335(18) 0.3513(8) -0.12827(19) 0.0280(10) Uani 1 1 d .
H14A H -0.0130 0.2114 -0.1516 0.042 Uiso 1 1 calc R
H14B H -0.0292 0.4812 -0.1536 0.042 Uiso 1 1 calc R
H14C H -0.0396 0.3266 -0.1001 0.042 Uiso 1 1 calc R
N1 N 0.17020(14) 0.5087(5) -0.05390(13) 0.0164(7) Uani 1 1 d .
H1D H 0.1537 0.3897 -0.0771 0.025 Uiso 1 1 calc R
H1E H 0.1932 0.4516 -0.0206 0.025 Uiso 1 1 calc R
H1F H 0.1942 0.5955 -0.0726 0.025 Uiso 1 1 calc R
O1 O 0.31578(12) 0.3558(5) 0.13249(11) 0.0201(6) Uani 1 1 d .
O2 O 0.25184(13) 0.6996(5) 0.10044(11) 0.0225(6) Uani 1 1 d .
O3 O 0.22336(12) 0.3179(5) 0.05539(10) 0.0199(6) Uani 1 1 d .
O4 O 0.04894(12) 0.4033(5) -0.09770(11) 0.0228(6) Uani 1 1 d .
S1 S 0.25319(4) 0.44478(17) 0.10872(4) 0.0162(2) 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 0.0181 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'
S S 0.3331 0.5567 '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
_geom_angle_site_symmetry_3
C2 C1 H1A 109.5 .
C2 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
C2 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
C3 C2 C7 118.1(4) .
C3 C2 C1 121.1(4) .
C7 C2 C1 120.8(4) .
C2 C3 C4 121.3(4) .
C2 C3 H3 119.3 .
C4 C3 H3 119.3 .
C3 C4 C5 119.8(4) .
C3 C4 H4 120.1 .
C5 C4 H4 120.1 .
C6 C5 C4 120.0(4) .
C6 C5 S1 120.0(3) .
C4 C5 S1 119.9(3) .
C5 C6 C7 119.5(4) .
C5 C6 H6 120.3 .
C7 C6 H6 120.3 .
C6 C7 C2 121.3(4) .
C6 C7 H7 119.4 .
C2 C7 H7 119.4 .
C9 C8 C13 120.2(3) .
C9 C8 N1 119.4(3) .
C13 C8 N1 120.4(3) .
C8 C9 C10 120.5(3) .
C8 C9 H9 119.7 .
C10 C9 H9 119.7 .
C9 C10 C11 120.8(4) .
C9 C10 H10 119.6 .
C11 C10 H10 119.6 .
C10 C11 C12 118.2(3) .
C10 C11 C11 121.6(4) 5_575
C12 C11 C11 120.2(4) 5_575
C13 C12 C11 120.8(3) .
C13 C12 H12 119.6 .
C11 C12 H12 119.6 .
O4 C13 C8 115.2(3) .
O4 C13 C12 125.2(3) .
C8 C13 C12 119.5(3) .
O4 C14 H14A 109.5 .
O4 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
O4 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
C8 N1 H1D 109.5 .
C8 N1 H1E 109.5 .
H1D N1 H1E 109.5 .
C8 N1 H1F 109.5 .
H1D N1 H1F 109.5 .
H1E N1 H1F 109.5 .
C13 O4 C14 118.4(3) .
O1 S1 O2 112.68(17) .
O1 S1 O3 111.88(16) .
O2 S1 O3 112.56(16) .
O1 S1 C5 107.72(16) .
O2 S1 C5 105.77(17) .
O3 S1 C5 105.66(16) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.506(5) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C3 1.383(6) .
C2 C7 1.399(6) .
C3 C4 1.385(5) .
C3 H3 0.9300 .
C4 C5 1.392(5) .
C4 H4 0.9300 .
C5 C6 1.382(5) .
C5 S1 1.772(4) .
C6 C7 1.390(5) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 C9 1.374(5) .
C8 C13 1.383(5) .
C8 N1 1.456(4) .
C9 C10 1.379(5) .
C9 H9 0.9300 .
C10 C11 1.393(5) .
C10 H10 0.9300 .
C11 C12 1.399(5) .
C11 C11 1.497(7) 5_575
C12 C13 1.392(5) .
C12 H12 0.9300 .
C13 O4 1.366(4) .
C14 O4 1.430(4) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
N1 H1D 0.8900 .
N1 H1E 0.8900 .
N1 H1F 0.8900 .
O1 S1 1.456(3) .
O2 S1 1.456(3) .
O3 S1 1.461(3) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C7 C2 C3 C4 1.4(6) . .
C1 C2 C3 C4 -179.8(4) . .
C2 C3 C4 C5 -0.1(6) . .
C3 C4 C5 C6 -1.5(5) . .
C3 C4 C5 S1 179.6(3) . .
C4 C5 C6 C7 1.7(5) . .
S1 C5 C6 C7 -179.4(3) . .
C5 C6 C7 C2 -0.3(6) . .
C3 C2 C7 C6 -1.2(6) . .
C1 C2 C7 C6 180.0(4) . .
C13 C8 C9 C10 1.4(6) . .
N1 C8 C9 C10 -178.0(3) . .
C8 C9 C10 C11 0.0(6) . .
C9 C10 C11 C12 -1.8(6) . .
C9 C10 C11 C11 177.0(4) . 5_575
C10 C11 C12 C13 2.4(5) . .
C11 C11 C12 C13 -176.5(4) 5_575 .
C9 C8 C13 O4 178.3(3) . .
N1 C8 C13 O4 -2.2(5) . .
C9 C8 C13 C12 -0.9(5) . .
N1 C8 C13 C12 178.6(3) . .
C11 C12 C13 O4 179.8(3) . .
C11 C12 C13 C8 -1.1(5) . .
C8 C13 O4 C14 -171.6(3) . .
C12 C13 O4 C14 7.5(5) . .
C6 C5 S1 O1 -88.6(3) . .
C4 C5 S1 O1 90.3(3) . .
C6 C5 S1 O2 150.7(3) . .
C4 C5 S1 O2 -30.4(3) . .
C6 C5 S1 O3 31.1(3) . .
C4 C5 S1 O3 -149.9(3) . .
