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#$Date: 2020-09-24 01:35:39 +0300 (Thu, 24 Sep 2020) $
#$Revision: 256675 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/52/4135259.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_4135259
loop_
_publ_author_name
'Wang, Jian-Cheng'
'Kan, Xuan'
'Shang, Jin-Yan'
'Qiao, Hua'
'Dong, Yu-Bin'
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Chiral Covalent Organic Frameworks from
 Prochiral Monomers for Heterogeneous Asymmetric Catalysis.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c07461
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_sum            'C15 H19 N O4'
_chemical_formula_weight         277.31
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.71444(17)
_cell_length_b                   8.4542(3)
_cell_length_c                   30.1647(9)
_cell_measurement_reflns_used    1837
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2100
_cell_measurement_theta_min      9.7350
_cell_volume                     1457.29(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0147
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            3031
_diffrn_reflns_point_group_measured_fraction_full 0.830
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        67.243
_diffrn_reflns_theta_max         67.243
_diffrn_reflns_theta_min         5.434
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 547 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0381
_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)+(0.0430P)²+0.3588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.398
_reflns_Friedel_fraction_full    0.587
_reflns_Friedel_fraction_max     0.587
_reflns_number_gt                1991
_reflns_number_total             2162
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c07461_si_003.cif
_cod_data_source_block           exp_11271
_cod_database_code               4135259
_shelx_shelxl_version_number     2018/3
_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   0.915
_shelx_estimated_absorpt_t_max   0.922
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.5791(4) 0.3857(3) 0.33606(7) 0.0480(6) Uani 1 1 d . . . . .
O1 O 0.4194(4) 0.8029(3) 0.26968(7) 0.0643(6) Uani 1 1 d . . . . .
O2 O 0.3080(5) 0.4722(3) 0.53381(6) 0.0736(7) Uani 1 1 d . . . . .
O3 O 0.7799(4) 0.4304(3) 0.33748(8) 0.0703(7) Uani 1 1 d . . . . .
O4 O 0.5181(5) 0.2528(3) 0.34541(9) 0.0812(7) Uani 1 1 d . . . . .
C1 C 0.2404(5) 0.8220(3) 0.29043(8) 0.0465(6) Uani 1 1 d . . . . .
C2 C 0.0420(6) 0.9216(4) 0.27360(10) 0.0614(8) Uani 1 1 d . . . . .
H2A H -0.100918 0.859792 0.273064 0.074 Uiso 1 1 calc R U . . .
H2B H 0.075166 0.956688 0.243632 0.074 Uiso 1 1 calc R U . . .
C3 C 0.0113(6) 1.0638(4) 0.30377(11) 0.0684(9) Uani 1 1 d . . . . .
H3A H 0.145782 1.133010 0.300807 0.082 Uiso 1 1 calc R U . . .
H3B H -0.126491 1.122537 0.294727 0.082 Uiso 1 1 calc R U . . .
C4 C -0.0145(6) 1.0145(4) 0.35189(10) 0.0690(9) Uani 1 1 d . . . . .
H4A H -0.162608 0.960072 0.355688 0.083 Uiso 1 1 calc R U . . .
H4B H -0.016925 1.108214 0.370421 0.083 Uiso 1 1 calc R U . . .
C5 C 0.1828(6) 0.9067(3) 0.36698(9) 0.0556(7) Uani 1 1 d . . . . .
H5A H 0.153330 0.872965 0.397207 0.067 Uiso 1 1 calc R U . . .
H5B H 0.328730 0.965271 0.366693 0.067 Uiso 1 1 calc R U . . .
C6 C 0.2066(4) 0.7602(3) 0.33707(8) 0.0412(6) Uani 1 1 d . . . . .
H6 H 0.057278 0.703177 0.337876 0.049 Uiso 1 1 calc R U . . .
C7 C 0.3986(5) 0.6455(3) 0.35246(8) 0.0394(6) Uani 1 1 d . . . . .
H7 H 0.549921 0.698663 0.349018 0.047 Uiso 1 1 calc R U . . .
C8 C 0.3717(4) 0.5989(3) 0.40090(8) 0.0390(6) Uani 1 1 d . . . . .
C9 C 0.5299(5) 0.6464(3) 0.43284(8) 0.0483(7) Uani 1 1 d . . . . .
H9 H 0.656889 0.708621 0.424606 0.058 Uiso 1 1 calc R U . . .
C10 C 0.5037(6) 0.6035(4) 0.47690(9) 0.0563(8) Uani 1 1 d . . . . .
H10 H 0.611892 0.637821 0.497823 0.068 Uiso 1 1 calc R U . . .
C11 C 0.3185(5) 0.5102(3) 0.48989(8) 0.0504(7) Uani 1 1 d . . . . .
C12 C 0.1586(5) 0.4622(4) 0.45857(9) 0.0590(8) Uani 1 1 d . . . . .
H12 H 0.031464 0.400151 0.466790 0.071 Uiso 1 1 calc R U . . .
C13 C 0.1879(5) 0.5069(4) 0.41466(9) 0.0565(8) Uani 1 1 d . . . . .
H13 H 0.078940 0.473249 0.393806 0.068 Uiso 1 1 calc R U . . .
C14 C 0.1159(8) 0.3764(6) 0.54751(11) 0.0897(13) Uani 1 1 d . . . . .
H14A H -0.028008 0.431598 0.542016 0.135 Uiso 1 1 calc R U . . .
H14B H 0.129406 0.354052 0.578613 0.135 Uiso 1 1 calc R U . . .
H14C H 0.116960 0.279026 0.531145 0.135 Uiso 1 1 calc R U . . .
C15 C 0.3968(5) 0.5006(3) 0.32210(8) 0.0436(6) Uani 1 1 d . . . . .
H15A H 0.244225 0.450519 0.323223 0.052 Uiso 1 1 calc R U . . .
H15B H 0.425706 0.533393 0.291770 0.052 Uiso 1 1 calc R U . . .
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'
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
_geom_angle_publ_flag
O3 N1 O4 123.8(3) . . ?
O3 N1 C15 118.1(2) . . ?
O4 N1 C15 118.1(3) . . ?
C11 O2 C14 116.7(3) . . ?
O1 C1 C2 122.6(2) . . ?
O1 C1 C6 122.9(2) . . ?
C2 C1 C6 114.3(2) . . ?
C1 C2 C3 109.2(2) . . ?
C4 C3 C2 111.5(3) . . ?
C3 C4 C5 112.3(3) . . ?
C4 C5 C6 111.9(2) . . ?
C1 C6 C7 114.1(2) . . ?
C1 C6 C5 106.2(2) . . ?
C7 C6 C5 113.2(2) . . ?
C8 C7 C15 111.5(2) . . ?
C8 C7 C6 112.5(2) . . ?
C15 C7 C6 108.6(2) . . ?
C13 C8 C9 117.1(2) . . ?
C13 C8 C7 121.0(2) . . ?
C9 C8 C7 121.9(2) . . ?
C8 C9 C10 121.5(3) . . ?
C11 C10 C9 120.4(3) . . ?
O2 C11 C12 124.6(3) . . ?
O2 C11 C10 116.4(3) . . ?
C12 C11 C10 119.0(2) . . ?
C11 C12 C13 119.7(3) . . ?
C8 C13 C12 122.4(3) . . ?
N1 C15 C7 110.5(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O3 1.209(3) . ?
N1 O4 1.210(3) . ?
N1 C15 1.486(3) . ?
O1 C1 1.210(3) . ?
O2 C11 1.365(3) . ?
O2 C14 1.426(5) . ?
C1 C2 1.501(4) . ?
C1 C6 1.513(3) . ?
C2 C3 1.518(4) . ?
C3 C4 1.518(5) . ?
C4 C5 1.519(4) . ?
C5 C6 1.539(4) . ?
C6 C7 1.536(3) . ?
C7 C8 1.521(3) . ?
C7 C15 1.530(3) . ?
C8 C13 1.371(4) . ?
C8 C9 1.381(3) . ?
C9 C10 1.386(4) . ?
C10 C11 1.376(4) . ?
C11 C12 1.375(4) . ?
C12 C13 1.387(4) . ?
