#------------------------------------------------------------------------------
#$Date: 2019-11-03 16:39:31 +0200 (Sun, 03 Nov 2019) $
#$Revision: 221902 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/88/4128837.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_4128837
loop_
_publ_author_name
'Li, Yusen'
'Chen, Qing'
'Xu, Tiantian'
'Xie, Zhen'
'Liu, Jingjuan'
'Yu, Xiang'
'Ma, Shengqian'
'Qin, Tianshi'
'Chen, Long'
_publ_section_title
;
 De Novo Design and Facile Synthesis of 2D Covalent Organic Frameworks: A
 Two-in-One Strategy.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13822
_journal_page_last               13828
_journal_paper_doi               10.1021/jacs.9b03463
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C42 H28 N2 O2'
_chemical_formula_sum            'C42 H28 N2 O2'
_chemical_formula_weight         592.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
????
;
_cell_angle_alpha                90
_cell_angle_beta                 90.01(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1503(12)
_cell_length_b                   12.927(3)
_cell_length_c                   21.540(4)
_cell_measurement_reflns_used    2764
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.8744
_cell_measurement_theta_min      1.8366
_cell_volume                     1712.5(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn 70'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1505
_diffrn_reflns_av_unetI/netI     0.1436
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            17927
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.885
_diffrn_reflns_theta_min         1.837
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Crystalclear
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       plate
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.1589
_refine_ls_R_factor_gt           0.0830
_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)+(0.0859P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1790
_refine_ls_wR_factor_ref         0.2174
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1902
_reflns_number_total             4067
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b03463_si_002.cif
_cod_data_source_block           r20180518c1_sq
_cod_original_cell_volume        1712.6(6)
_cod_database_code               4128837
_shelx_shelxl_version_number     2017/1
_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_max   0.989
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Rotating group:
 N1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
O1 O 0.1666(5) 0.93350(18) 0.24208(11) 0.0497(7) Uani 1 1 d .
N1 N 0.6522(6) 0.0129(2) 0.24702(13) 0.0477(8) Uani 1 1 d .
H1A H 0.730778 0.017353 0.281210 0.057 Uiso 1 1 d GR
H1B H 0.513604 0.006736 0.257003 0.057 Uiso 1 1 d GR
C1 C 1.0579(6) 0.3150(2) 0.03829(14) 0.0328(8) Uani 1 1 d .
H1 H 1.049740 0.249882 0.058595 0.039 Uiso 1 1 calc R
C2 C 0.9034(6) 0.3943(2) 0.05438(13) 0.0289(7) Uani 1 1 d .
C3 C 0.7429(6) 0.3788(2) 0.10042(13) 0.0298(7) Uani 1 1 d .
C4 C 0.5987(6) 0.4595(2) 0.11336(14) 0.0341(8) Uani 1 1 d .
H4 H 0.486778 0.447844 0.142940 0.041 Uiso 1 1 calc R
C5 C 0.6108(5) 0.5564(2) 0.08498(13) 0.0294(7) Uani 1 1 d .
C6 C 0.7694(5) 0.5725(2) 0.03829(13) 0.0273(7) Uani 1 1 d .
C7 C 0.7865(6) 0.6696(2) 0.00464(13) 0.0332(8) Uani 1 1 d .
H7 H 0.685626 0.723411 0.013142 0.040 Uiso 1 1 calc R
C8 C 0.9167(5) 0.4917(2) 0.02312(12) 0.0261(7) Uani 1 1 d .
C9 C 0.7211(6) 0.2792(2) 0.13676(13) 0.0292(8) Uani 1 1 d .
C10 C 0.8934(6) 0.2452(2) 0.17378(14) 0.0357(8) Uani 1 1 d .
H10 H 1.026327 0.282585 0.173626 0.043 Uiso 1 1 calc R
C11 C 0.8739(6) 0.1575(2) 0.21091(14) 0.0377(8) Uani 1 1 d .
H11 H 0.993272 0.134871 0.235389 0.045 Uiso 1 1 calc R
C12 C 0.6767(6) 0.1028(2) 0.21194(14) 0.0356(8) Uani 1 1 d .
C13 C 0.5044(6) 0.1391(3) 0.17536(15) 0.0407(9) Uani 1 1 d .
H13 H 0.369447 0.103418 0.175176 0.049 Uiso 1 1 calc R
C14 C 0.5312(6) 0.2276(2) 0.13930(14) 0.0383(9) Uani 1 1 d .
H14 H 0.411508 0.252351 0.115705 0.046 Uiso 1 1 calc R
C15 C 0.4702(6) 0.6396(2) 0.11097(13) 0.0315(8) Uani 1 1 d .
C16 C 0.2567(6) 0.6177(3) 0.12862(14) 0.0350(8) Uani 1 1 d .
H16 H 0.194348 0.552737 0.118210 0.042 Uiso 1 1 calc R
C17 C 0.1342(6) 0.6899(2) 0.16125(14) 0.0363(8) Uani 1 1 d .
H17 H -0.011587 0.674102 0.172302 0.044 Uiso 1 1 calc R
C18 C 0.2225(6) 0.7846(2) 0.17786(14) 0.0354(8) Uani 1 1 d .
C19 C 0.4326(6) 0.8084(3) 0.15916(15) 0.0385(9) Uani 1 1 d .
H19 H 0.492444 0.874119 0.169131 0.046 Uiso 1 1 calc R
C20 C 0.5562(6) 0.7378(2) 0.12618(13) 0.0359(8) Uani 1 1 d .
H20 H 0.699612 0.755376 0.113694 0.043 Uiso 1 1 calc R
C21 C 0.0972(7) 0.8551(3) 0.21782(15) 0.0437(9) Uani 1 1 d .
H21 H -0.050742 0.838032 0.225333 0.052 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
H1A N1 H1B 109.4 . .
C12 N1 H1A 109.8 . .
C12 N1 H1B 108.2 . .
C2 C1 H1 119.0 . .
C7 C1 H1 119.0 3_765 .
C7 C1 C2 122.0(3) 3_765 .
C3 C2 C1 121.9(3) . .
C3 C2 C8 119.7(3) . .
C8 C2 C1 118.4(3) . .
C2 C3 C9 123.1(3) . .
C4 C3 C2 118.5(3) . .
C4 C3 C9 118.4(3) . .
C3 C4 H4 118.4 . .
C5 C4 C3 123.3(3) . .
C5 C4 H4 118.4 . .
C4 C5 C6 118.7(3) . .
C4 C5 C15 116.9(3) . .
C6 C5 C15 124.1(3) . .
C5 C6 C7 122.1(3) . .
C5 C6 C8 119.6(3) . .
C8 C6 C7 118.3(3) . .
C1 C7 C6 121.5(3) 3_765 .
C1 C7 H7 119.3 3_765 .
C6 C7 H7 119.3 . .
C2 C8 C8 119.7(3) . 3_765
C6 C8 C2 120.2(3) . .
C6 C8 C8 120.1(3) . 3_765
C10 C9 C3 119.7(3) . .
C14 C9 C3 121.3(3) . .
C14 C9 C10 118.6(3) . .
C9 C10 H10 119.4 . .
C11 C10 C9 121.3(3) . .
C11 C10 H10 119.4 . .
C10 C11 H11 120.2 . .
C10 C11 C12 119.6(3) . .
C12 C11 H11 120.2 . .
N1 C12 C11 121.5(3) . .
N1 C12 C13 120.1(3) . .
C13 C12 C11 118.4(3) . .
C12 C13 H13 120.0 . .
C14 C13 C12 120.0(3) . .
C14 C13 H13 120.0 . .
C9 C14 C13 122.2(3) . .
C9 C14 H14 118.9 . .
C13 C14 H14 118.9 . .
C16 C15 C5 120.2(3) . .
C16 C15 C20 118.1(3) . .
C20 C15 C5 121.2(3) . .
C15 C16 H16 119.6 . .
C17 C16 C15 120.8(3) . .
C17 C16 H16 119.6 . .
C16 C17 H17 119.6 . .
C18 C17 C16 120.7(3) . .
C18 C17 H17 119.6 . .
C17 C18 C19 119.0(3) . .
C17 C18 C21 119.5(3) . .
C19 C18 C21 121.3(3) . .
C18 C19 H19 119.6 . .
C20 C19 C18 120.9(3) . .
C20 C19 H19 119.6 . .
C15 C20 H20 119.8 . .
C19 C20 C15 120.4(3) . .
C19 C20 H20 119.8 . .
O1 C21 C18 125.6(4) . .
O1 C21 H21 117.2 . .
C18 C21 H21 117.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C21 1.217(4) .
N1 H1A 0.8828 .
N1 H1B 0.8825 .
N1 C12 1.395(4) .
C1 H1 0.9500 .
C1 C2 1.440(4) .
C1 C7 1.345(4) 3_765
C2 C3 1.414(4) .
C2 C8 1.430(4) .
C3 C4 1.398(4) .
C3 C9 1.513(4) .
C4 H4 0.9500 .
C4 C5 1.396(4) .
C5 C6 1.416(4) .
C5 C15 1.490(4) .
C6 C7 1.453(4) .
C6 C8 1.421(4) .
C7 H7 0.9500 .
C8 C8 1.445(6) 3_765
C9 C10 1.397(4) .
C9 C14 1.346(5) .
C10 H10 0.9500 .
C10 C11 1.392(4) .
C11 H11 0.9500 .
C11 C12 1.404(5) .
C12 C13 1.401(5) .
C13 H13 0.9500 .
C13 C14 1.392(4) .
C14 H14 0.9500 .
C15 C16 1.396(5) .
C15 C20 1.414(4) .
C16 H16 0.9500 .
C16 C17 1.390(4) .
C17 H17 0.9500 .
C17 C18 1.387(5) .
C18 C19 1.388(5) .
C18 C21 1.472(4) .
C19 H19 0.9500 .
C19 C20 1.384(4) .
C20 H20 0.9500 .
C21 H21 0.9500 .
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
N1 C12 C13 C14 -178.5(3) . .
C1 C2 C3 C4 -179.9(3) . .
C1 C2 C3 C9 0.6(5) . .
C1 C2 C8 C6 -179.1(3) . .
C1 C2 C8 C8 -0.3(5) . 3_765
C2 C3 C4 C5 -2.8(5) . .
C2 C3 C9 C10 60.8(4) . .
C2 C3 C9 C14 -126.1(3) . .
C3 C2 C8 C6 0.1(4) . .
C3 C2 C8 C8 178.9(3) . 3_765
C3 C4 C5 C6 3.5(5) . .
C3 C4 C5 C15 -170.1(3) . .
C3 C9 C10 C11 175.8(3) . .
C3 C9 C14 C13 -176.2(3) . .
C4 C3 C9 C10 -118.7(3) . .
C4 C3 C9 C14 54.5(4) . .
C4 C5 C6 C7 177.3(3) . .
C4 C5 C6 C8 -2.4(4) . .
C4 C5 C15 C16 -41.4(4) . .
C4 C5 C15 C20 130.0(3) . .
C5 C6 C7 C1 178.0(3) . 3_765
C5 C6 C8 C2 0.6(4) . .
C5 C6 C8 C8 -178.1(3) . 3_765
C5 C15 C16 C17 170.4(3) . .
C5 C15 C20 C19 -169.7(3) . .
C6 C5 C15 C16 145.4(3) . .
C6 C5 C15 C20 -43.3(4) . .
C7 C1 C2 C3 -178.7(3) 3_765 .
C7 C1 C2 C8 0.5(5) 3_765 .
C7 C6 C8 C2 -179.0(3) . .
C7 C6 C8 C8 2.2(5) . 3_765
C8 C2 C3 C4 1.0(5) . .
C8 C2 C3 C9 -178.5(3) . .
C8 C6 C7 C1 -2.4(5) . 3_765
C9 C3 C4 C5 176.6(3) . .
C9 C10 C11 C12 -0.9(5) . .
C10 C9 C14 C13 -3.0(5) . .
C10 C11 C12 N1 178.1(3) . .
C10 C11 C12 C13 -0.3(5) . .
C11 C12 C13 C14 -0.1(5) . .
C12 C13 C14 C9 1.8(5) . .
C14 C9 C10 C11 2.5(5) . .
C15 C5 C6 C7 -9.6(5) . .
C15 C5 C6 C8 170.8(3) . .
C15 C16 C17 C18 -1.0(5) . .
C16 C15 C20 C19 1.8(5) . .
C16 C17 C18 C19 2.7(5) . .
C16 C17 C18 C21 -173.8(3) . .
C17 C18 C19 C20 -2.2(5) . .
C17 C18 C21 O1 169.8(3) . .
C18 C19 C20 C15 -0.1(5) . .
C19 C18 C21 O1 -6.6(5) . .
C20 C15 C16 C17 -1.2(5) . .
C21 C18 C19 C20 174.3(3) . .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.021 0.000 0.000 183 47 ' '
2 -0.035 0.500 0.500 183 47 ' '
