#------------------------------------------------------------------------------
#$Date: 2017-03-04 15:45:33 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193495 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/54/4125498.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_4125498
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         'C12 H13 N2, C7 H7 O3 S'
_chemical_formula_sum            'C19 H20 N2 O3 S'
_chemical_formula_weight         356.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 93.037(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   11.036(5)
_cell_length_b                   5.946(5)
_cell_length_c                   27.498(5)
_cell_measurement_reflns_used    3358
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.50
_cell_volume                     1801.9(18)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.968
_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  0.0286
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            6172
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.786
_diffrn_reflns_theta_min         1.483
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Crysalispro
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.253
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.253
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0769
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0138P)²+5.6564P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1939
_refine_ls_wR_factor_ref         0.2017
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2713
_reflns_number_total             3358
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b08815_si_002.cif
_cod_data_source_block           PTSA-BD
_cod_depositor_comments
'Adding full bibliography for 4125492--4125502.cif.'
_cod_database_code               4125498
_shelx_shelxl_version_number     2014/7
_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   0.950
_shelx_estimated_absorpt_t_max   0.967
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.5813(5) -0.1126(11) 0.3753(2) 0.0701(17) Uani 1 1 d . . .
H1A H 0.6081 -0.1866 0.4050 0.105 Uiso 1 1 calc R U .
H1B H 0.6266 0.0237 0.3718 0.105 Uiso 1 1 calc R U .
H1C H 0.5940 -0.2100 0.3482 0.105 Uiso 1 1 calc R U .
C2 C 0.4483(4) -0.0579(9) 0.37675(16) 0.0480(12) Uani 1 1 d . . .
C3 C 0.4019(5) 0.1476(9) 0.36112(19) 0.0566(13) Uani 1 1 d . . .
H3 H 0.4546 0.2562 0.3502 0.068 Uiso 1 1 calc R U .
C4 C 0.2800(5) 0.1953(9) 0.36136(18) 0.0514(12) Uani 1 1 d . . .
H4 H 0.2509 0.3333 0.3499 0.062 Uiso 1 1 calc R U .
C5 C 0.2013(4) 0.0384(8) 0.37858(16) 0.0442(11) Uani 1 1 d . . .
C6 C 0.2458(5) -0.1670(9) 0.39491(19) 0.0542(13) Uani 1 1 d . . .
H6 H 0.1934 -0.2739 0.4068 0.065 Uiso 1 1 calc R U .
C7 C 0.3671(5) -0.2126(9) 0.39357(18) 0.0555(13) Uani 1 1 d . . .
H7 H 0.3957 -0.3520 0.4043 0.067 Uiso 1 1 calc R U .
C8 C 0.1924(4) 0.4430(8) 0.53009(16) 0.0399(10) Uani 1 1 d . . .
C9 C 0.2474(4) 0.2786(9) 0.50426(18) 0.0511(12) Uani 1 1 d . . .
H9 H 0.2039 0.1510 0.4945 0.061 Uiso 1 1 calc R U .
C10 C 0.3673(4) 0.3008(9) 0.49264(17) 0.0489(12) Uani 1 1 d . . .
H10 H 0.4031 0.1868 0.4752 0.059 Uiso 1 1 calc R U .
C11 C 0.4355(4) 0.4879(8) 0.50626(16) 0.0387(10) Uani 1 1 d . . .
C12 C 0.3772(5) 0.6515(9) 0.5318(2) 0.0668(17) Uani 1 1 d . . .
H12 H 0.4199 0.7803 0.5414 0.080 Uiso 1 1 calc R U .
C13 C 0.2577(4) 0.6310(9) 0.5437(2) 0.0641(16) Uani 1 1 d . . .
H13 H 0.2214 0.7449 0.5610 0.077 Uiso 1 1 calc R U .
C14 C 0.8150(4) 0.5674(8) 0.28037(16) 0.0432(11) Uani 1 1 d . . .
C15 C 0.7492(4) 0.3756(9) 0.28893(18) 0.0491(12) Uani 1 1 d . . .
H15 H 0.7874 0.2512 0.3034 0.059 Uiso 1 1 calc R U .
C16 C 0.6277(4) 0.3682(8) 0.27621(18) 0.0488(12) Uani 1 1 d . . .
H16 H 0.5850 0.2364 0.2816 0.059 Uiso 1 1 calc R U .
C17 C 0.5661(4) 0.5512(8) 0.25555(15) 0.0398(10) Uani 1 1 d . . .
C18 C 0.6352(4) 0.7403(8) 0.24562(17) 0.0471(11) Uani 1 1 d . . .
H18 H 0.5976 0.8638 0.2306 0.056 Uiso 1 1 calc R U .
C19 C 0.7583(4) 0.7482(9) 0.25762(17) 0.0489(12) Uani 1 1 d . . .
H19 H 0.8028 0.8755 0.2503 0.059 Uiso 1 1 calc R U .
N1 N 0.0668(3) 0.4240(7) 0.54051(15) 0.0495(10) Uani 1 1 d . . .
H1D H 0.0209 0.4621 0.5142 0.074 Uiso 0.5 1 calc R U P
H1E H 0.0510 0.5153 0.5650 0.074 Uiso 1 1 calc R U .
H1F H 0.0507 0.2828 0.5487 0.074 Uiso 1 1 calc R U .
N2 N 0.9428(3) 0.5793(8) 0.29273(15) 0.0530(11) Uani 1 1 d . . .
H2A H 0.9836 0.5682 0.2658 0.080 Uiso 0.5 1 calc R U P
H2B H 0.9640 0.4671 0.3128 0.080 Uiso 1 1 calc R U .
H2C H 0.9600 0.7101 0.3072 0.080 Uiso 1 1 calc R U .
O1 O 0.0327(3) 0.3407(6) 0.37905(14) 0.0647(11) Uani 1 1 d . . .
O2 O 0.0040(4) 0.0081(8) 0.4247(2) 0.1009(18) Uani 1 1 d . . .
O3 O -0.0103(4) 0.0043(11) 0.3360(2) 0.137(3) Uani 1 1 d . . .
S1 S 0.04440(12) 0.0991(2) 0.37972(6) 0.0567(4) 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
_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 .
C7 C2 C3 117.1(5) .
C7 C2 C1 121.0(5) .
C3 C2 C1 121.8(5) .
C4 C3 C2 121.7(5) .
C4 C3 H3 119.1 .
C2 C3 H3 119.1 .
C5 C4 C3 119.8(5) .
C5 C4 H4 120.1 .
C3 C4 H4 120.1 .
C4 C5 C6 119.4(5) .
C4 C5 S1 120.3(4) .
C6 C5 S1 120.3(4) .
C7 C6 C5 119.8(5) .
C7 C6 H6 120.1 .
C5 C6 H6 120.1 .
C6 C7 C2 122.0(5) .
C6 C7 H7 119.0 .
C2 C7 H7 119.0 .
C9 C8 C13 118.9(4) .
C9 C8 N1 120.4(4) .
C13 C8 N1 120.6(4) .
C8 C9 C10 120.5(5) .
C8 C9 H9 119.8 .
C10 C9 H9 119.8 .
C11 C10 C9 121.8(5) .
C11 C10 H10 119.1 .
C9 C10 H10 119.1 .
C12 C11 C10 116.4(4) .
C12 C11 C11 121.8(5) 3_666
C10 C11 C11 121.9(5) 3_666
C11 C12 C13 122.4(5) .
C11 C12 H12 118.8 .
C13 C12 H12 118.8 .
C8 C13 C12 120.1(5) .
C8 C13 H13 119.9 .
C12 C13 H13 119.9 .
C19 C14 C15 119.5(4) .
C19 C14 N2 119.1(4) .
C15 C14 N2 121.4(4) .
C16 C15 C14 120.1(5) .
C16 C15 H15 120.0 .
C14 C15 H15 120.0 .
C15 C16 C17 122.1(5) .
C15 C16 H16 119.0 .
C17 C16 H16 119.0 .
C16 C17 C18 116.9(4) .
C16 C17 C17 122.8(3) 2_655
C18 C17 C17 120.3(3) 2_655
C19 C18 C17 121.5(4) .
C19 C18 H18 119.3 .
C17 C18 H18 119.3 .
C14 C19 C18 119.9(5) .
C14 C19 H19 120.0 .
C18 C19 H19 120.0 .
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 .
C14 N2 H2A 109.5 .
C14 N2 H2B 109.5 .
H2A N2 H2B 109.5 .
C14 N2 H2C 109.5 .
H2A N2 H2C 109.5 .
H2B N2 H2C 109.5 .
O3 S1 O2 115.9(4) .
O3 S1 O1 110.3(3) .
O2 S1 O1 110.7(3) .
O3 S1 C5 105.9(3) .
O2 S1 C5 106.6(2) .
O1 S1 C5 106.8(2) .
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(7) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C7 1.381(7) .
C2 C3 1.384(7) .
C3 C4 1.376(7) .
C3 H3 0.9300 .
C4 C5 1.375(7) .
C4 H4 0.9300 .
C5 C6 1.382(7) .
C5 S1 1.771(5) .
C6 C7 1.368(7) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 C9 1.369(6) .
C8 C13 1.371(7) .
C8 N1 1.435(5) .
C9 C10 1.384(6) .
C9 H9 0.9300 .
C10 C11 1.383(6) .
C10 H10 0.9300 .
C11 C12 1.379(7) .
C11 C11 1.490(9) 3_666
C12 C13 1.381(7) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 C19 1.377(7) .
C14 C15 1.379(7) .
C14 N2 1.435(6) .
C15 C16 1.368(6) .
C15 H15 0.9300 .
C16 C17 1.388(6) .
C16 H16 0.9300 .
C17 C18 1.393(6) .
C17 C17 1.476(9) 2_655
C18 C19 1.382(6) .
C18 H18 0.9300 .
C19 H19 0.9300 .
N1 H1D 0.8900 .
N1 H1E 0.8900 .
N1 H1F 0.8900 .
N2 H2A 0.8900 .
N2 H2B 0.8900 .
N2 H2C 0.8900 .
O1 S1 1.443(4) .
O2 S1 1.443(5) .
O3 S1 1.431(5) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1D N1 0.89 1.87 2.758(8) 173.2 3_566
N1 H1E O1 0.89 2.03 2.883(6) 161.6 3_566
N1 H1F O2 0.89 1.98 2.864(6) 170.0 3_556
N2 H2A N2 0.89 1.84 2.726(8) 172.4 2_755
N2 H2B O1 0.89 2.08 2.895(6) 152.6 1_655
N2 H2C O3 0.89 1.94 2.830(7) 176.2 1_665
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 -1.2(7) . .
C1 C2 C3 C4 178.4(5) . .
C2 C3 C4 C5 1.6(8) . .
C3 C4 C5 C6 -0.8(7) . .
C3 C4 C5 S1 179.3(4) . .
C4 C5 C6 C7 -0.3(8) . .
S1 C5 C6 C7 179.6(4) . .
C5 C6 C7 C2 0.7(8) . .
C3 C2 C7 C6 0.0(8) . .
C1 C2 C7 C6 -179.6(5) . .
C13 C8 C9 C10 0.8(8) . .
N1 C8 C9 C10 177.6(5) . .
C8 C9 C10 C11 -0.3(8) . .
C9 C10 C11 C12 -0.3(8) . .
C9 C10 C11 C11 -179.9(5) . 3_666
C10 C11 C12 C13 0.5(9) . .
C11 C11 C12 C13 -179.9(6) 3_666 .
C9 C8 C13 C12 -0.6(9) . .
N1 C8 C13 C12 -177.4(5) . .
C11 C12 C13 C8 0.0(10) . .
C19 C14 C15 C16 -2.0(7) . .
N2 C14 C15 C16 -179.2(4) . .
C14 C15 C16 C17 -1.4(8) . .
C15 C16 C17 C18 3.6(7) . .
C15 C16 C17 C17 -176.0(5) . 2_655
C16 C17 C18 C19 -2.6(7) . .
C17 C17 C18 C19 177.1(5) 2_655 .
C15 C14 C19 C18 3.0(7) . .
N2 C14 C19 C18 -179.7(4) . .
C17 C18 C19 C14 -0.7(7) . .
C4 C5 S1 O3 95.9(5) . .
C6 C5 S1 O3 -84.0(5) . .
C4 C5 S1 O2 -140.1(4) . .
C6 C5 S1 O2 40.0(5) . .
C4 C5 S1 O1 -21.7(5) . .
C6 C5 S1 O1 158.4(4) . .
