#------------------------------------------------------------------------------
#$Date: 2017-03-04 15:45:33 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193495 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/55/4125502.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_4125502
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         'C7 H7 O3 S, C6 H8 N3 O2'
_chemical_formula_sum            'C13 H15 N3 O5 S'
_chemical_formula_weight         325.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7115(2)
_cell_length_b                   12.5511(3)
_cell_length_c                   17.2878(5)
_cell_measurement_reflns_used    2193
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.30
_cell_volume                     1456.27(7)
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Supernova (Mo)X-Ray Source'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3804
_diffrn_reflns_point_group_measured_fraction_full 0.861
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.256
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Crysalispro
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 641 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0536P)²+0.4196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.474
_reflns_Friedel_fraction_full    0.668
_reflns_Friedel_fraction_max     0.668
_reflns_number_gt                2069
_reflns_number_total             2193
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b08815_si_002.cif
_cod_data_source_block           PTSA-Pa-NO2
_cod_depositor_comments
'Adding full bibliography for 4125492--4125502.cif.'
_cod_database_code               4125502
_shelx_shelxl_version_number     2016/4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.938
_shelx_estimated_absorpt_t_max   0.952
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.8588(8) 0.2258(3) 0.6012(3) 0.0623(12) Uani 1 1 d . .
H1A H 0.794944 0.183163 0.640081 0.093 Uiso 1 1 calc R U
H1B H 0.887146 0.182621 0.556764 0.093 Uiso 1 1 calc R U
H1C H 0.980911 0.254278 0.621506 0.093 Uiso 1 1 calc R U
C2 C 0.7229(6) 0.3161(3) 0.5783(2) 0.0399(9) Uani 1 1 d . .
C3 C 0.7812(5) 0.3891(3) 0.5229(2) 0.0424(8) Uani 1 1 d . .
H3 H 0.905102 0.381720 0.499443 0.051 Uiso 1 1 calc R U
C4 C 0.6603(5) 0.4724(3) 0.5018(2) 0.0363(8) Uani 1 1 d . .
H4 H 0.702501 0.520667 0.464491 0.044 Uiso 1 1 calc R U
C5 C 0.4756(5) 0.4844(2) 0.53621(18) 0.0296(7) Uani 1 1 d . .
C6 C 0.4132(6) 0.4117(3) 0.59075(19) 0.0375(8) Uani 1 1 d . .
H6 H 0.288518 0.418836 0.613622 0.045 Uiso 1 1 calc R U
C7 C 0.5360(6) 0.3285(3) 0.6113(2) 0.0424(9) Uani 1 1 d . .
H7 H 0.492778 0.279644 0.648152 0.051 Uiso 1 1 calc R U
C8 C 0.8183(5) 0.4530(3) 0.75926(18) 0.0305(7) Uani 1 1 d . .
C9 C 0.8731(5) 0.5248(3) 0.70087(19) 0.0326(7) Uani 1 1 d . .
H9 H 0.995907 0.518447 0.676356 0.039 Uiso 1 1 calc R U
C10 C 0.7455(5) 0.6036(3) 0.68058(17) 0.0304(7) Uani 1 1 d . .
C11 C 0.5636(5) 0.6153(3) 0.7187(2) 0.0359(8) Uani 1 1 d . .
H11 H 0.478131 0.670560 0.705075 0.043 Uiso 1 1 calc R U
C12 C 0.5114(5) 0.5464(3) 0.77544(19) 0.0381(8) Uani 1 1 d . .
H12 H 0.390112 0.556134 0.800480 0.046 Uiso 1 1 calc R U
C13 C 0.6344(5) 0.4601(3) 0.79823(18) 0.0304(7) Uani 1 1 d . .
N1 N 0.5702(4) 0.3930(2) 0.85305(16) 0.0411(7) Uani 1 1 d . .
H1D H 0.643538 0.340256 0.867127 0.049 Uiso 1 1 calc R U
H1E H 0.455658 0.402679 0.874198 0.049 Uiso 1 1 calc R U
N2 N 0.7945(4) 0.6736(2) 0.61566(15) 0.0338(6) Uani 1 1 d . .
H2A H 0.690248 0.678251 0.584044 0.041 Uiso 1 1 calc R U
H2B H 0.898260 0.647124 0.590005 0.041 Uiso 1 1 calc R U
H2C H 0.824926 0.738165 0.633458 0.041 Uiso 1 1 calc R U
N3 N 0.9551(5) 0.3687(2) 0.77529(16) 0.0381(7) Uani 1 1 d . .
O1 O 0.4314(4) 0.68922(18) 0.53794(16) 0.0462(7) Uani 1 1 d . .
O2 O 0.3095(4) 0.5944(2) 0.42784(13) 0.0495(7) Uani 1 1 d . .
O3 O 0.1371(4) 0.5799(2) 0.54956(18) 0.0549(8) Uani 1 1 d . .
O4 O 0.8976(4) 0.2921(2) 0.81417(16) 0.0554(8) Uani 1 1 d . .
O5 O 1.1253(4) 0.3724(2) 0.74947(16) 0.0532(7) Uani 1 1 d . .
S1 S 0.32546(12) 0.59519(6) 0.51120(4) 0.0307(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 0.0033 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'
S S 0.1246 0.1234 '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
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 117.9(3)
C3 C2 C1 120.6(4)
C7 C2 C1 121.5(4)
C4 C3 C2 121.4(3)
C4 C3 H3 119.3
C2 C3 H3 119.3
C3 C4 C5 119.9(3)
C3 C4 H4 120.0
C5 C4 H4 120.0
C6 C5 C4 119.7(3)
C6 C5 S1 120.9(3)
C4 C5 S1 119.4(2)
C5 C6 C7 119.8(3)
C5 C6 H6 120.1
C7 C6 H6 120.1
C6 C7 C2 121.3(3)
C6 C7 H7 119.4
C2 C7 H7 119.4
C9 C8 C13 122.3(3)
C9 C8 N3 116.5(3)
C13 C8 N3 121.1(3)
C10 C9 C8 119.3(3)
C10 C9 H9 120.4
C8 C9 H9 120.4
C9 C10 C11 120.6(3)
C9 C10 N2 119.7(3)
C11 C10 N2 119.7(3)
C12 C11 C10 120.1(3)
C12 C11 H11 120.0
C10 C11 H11 120.0
C11 C12 C13 122.6(3)
C11 C12 H12 118.7
C13 C12 H12 118.7
N1 C13 C8 125.5(3)
N1 C13 C12 119.3(3)
C8 C13 C12 115.1(3)
C13 N1 H1D 120.0
C13 N1 H1E 120.0
H1D N1 H1E 120.0
C10 N2 H2A 109.5
C10 N2 H2B 109.5
H2A N2 H2B 109.5
C10 N2 H2C 109.5
H2A N2 H2C 109.5
H2B N2 H2C 109.5
O5 N3 O4 121.2(3)
O5 N3 C8 120.0(3)
O4 N3 C8 118.8(3)
O3 S1 O2 113.16(18)
O3 S1 O1 113.01(17)
O2 S1 O1 111.06(17)
O3 S1 C5 106.41(16)
O2 S1 C5 106.26(16)
O1 S1 C5 106.37(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.508(5)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.381(5)
C2 C7 1.387(5)
C3 C4 1.372(5)
C3 H3 0.9300
C4 C5 1.383(5)
C4 H4 0.9300
C5 C6 1.377(5)
C5 S1 1.771(3)
C6 C7 1.377(5)
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.402(5)
C8 C13 1.408(5)
C8 N3 1.429(4)
C9 C10 1.354(5)
C9 H9 0.9300
C10 C11 1.395(5)
C10 N2 1.463(4)
C11 C12 1.354(5)
C11 H11 0.9300
C12 C13 1.419(5)
C12 H12 0.9300
C13 N1 1.339(4)
N1 H1D 0.8600
N1 H1E 0.8600
N2 H2A 0.8900
N2 H2B 0.8900
N2 H2C 0.8900
N3 O5 1.227(4)
N3 O4 1.235(4)
O1 S1 1.453(2)
O2 S1 1.445(2)
O3 S1 1.441(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
C7 C2 C3 C4 0.9(5)
C1 C2 C3 C4 -179.3(3)
C2 C3 C4 C5 0.0(5)
C3 C4 C5 C6 -0.8(5)
C3 C4 C5 S1 177.5(3)
C4 C5 C6 C7 0.8(5)
S1 C5 C6 C7 -177.5(3)
C5 C6 C7 C2 0.1(5)
C3 C2 C7 C6 -1.0(5)
C1 C2 C7 C6 179.3(4)
C13 C8 C9 C10 -0.4(5)
N3 C8 C9 C10 177.0(3)
C8 C9 C10 C11 1.8(5)
C8 C9 C10 N2 -175.2(3)
C9 C10 C11 C12 -1.3(5)
N2 C10 C11 C12 175.7(3)
C10 C11 C12 C13 -0.7(5)
C9 C8 C13 N1 178.3(3)
N3 C8 C13 N1 1.1(5)
C9 C8 C13 C12 -1.5(5)
N3 C8 C13 C12 -178.7(3)
C11 C12 C13 N1 -177.8(3)
C11 C12 C13 C8 2.0(5)
C9 C8 N3 O5 13.3(5)
C13 C8 N3 O5 -169.3(3)
C9 C8 N3 O4 -165.5(3)
C13 C8 N3 O4 11.9(5)
C6 C5 S1 O3 -7.6(3)
C4 C5 S1 O3 174.1(3)
C6 C5 S1 O2 -128.4(3)
C4 C5 S1 O2 53.3(3)
C6 C5 S1 O1 113.2(3)
C4 C5 S1 O1 -65.1(3)
