#------------------------------------------------------------------------------
#$Date: 2019-11-12 04:17:52 +0200 (Tue, 12 Nov 2019) $
#$Revision: 227525 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/35/4033506.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_4033506
loop_
_publ_author_name
'Chang, Meng-Yang'
'Chen, Yu-Hsin'
'Wang, Heui-Sin'
_publ_section_title
;
 Cu(OAc)₂ Mediated Synthesis of 3-Sulfonyl Chromen-4-ones.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2361
_journal_page_last               2368
_journal_paper_doi               10.1021/acs.joc.8b00177
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C42 H30 N6 O3'
_chemical_formula_weight         666.72
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 95.622(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9308(11)
_cell_length_b                   15.169(3)
_cell_length_c                   17.477(3)
_cell_measurement_reflns_used    2452
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.9412
_cell_measurement_theta_min      2.6855
_cell_volume                     1564.7(5)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15116
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.429
_diffrn_reflns_theta_min         1.781
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.8628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Columnar
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3214
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0476P)²+0.2129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1118
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2186
_reflns_number_total             3214
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b00177_si_001.cif
_cod_data_source_block           mo_170233LT_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033500--4033507.cif.
;
_cod_database_code               4033506
_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.
;
_shelxl_version_number           2014/6
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7846(2) 0.29543(8) 0.38719(7) 0.0496(3) Uani 1 1 d . . . A 2
C1 C 0.6069(3) 0.23939(11) 0.37471(9) 0.0382(4) Uani 1 1 d . . . A 2
C2 C 0.4294(3) 0.23639(10) 0.42334(9) 0.0348(4) Uani 1 1 d . . . A 2
C3 C 0.2539(3) 0.17581(11) 0.40492(10) 0.0398(4) Uani 1 1 d . . . A 2
H3 H 0.1332 0.1722 0.4367 0.048 Uiso 1 1 calc R U . A 2
C4 C 0.2525(3) 0.12147(11) 0.34192(10) 0.0468(4) Uani 1 1 d . . . A 2
H4 H 0.1317 0.0809 0.3307 0.056 Uiso 1 1 calc R U . A 2
C5 C 0.4270(3) 0.12565(12) 0.29476(10) 0.0480(5) Uani 1 1 d . . . A 2
H5 H 0.4253 0.0882 0.2511 0.058 Uiso 1 1 calc R U . A 2
C6 C 0.6025(3) 0.18390(12) 0.31108(10) 0.0467(5) Uani 1 1 d . . . A 2
H6 H 0.7220 0.1864 0.2787 0.056 Uiso 1 1 calc R U . A 2
C7 C 0.4275(3) 0.29547(10) 0.48962(9) 0.0339(4) Uani 1 1 d . . . A 2
C8 C 0.2491(3) 0.29503(12) 0.53962(10) 0.0452(4) Uani 1 1 d . . . A 2
H8 H 0.1327 0.2522 0.5305 0.054 Uiso 1 1 calc R U . A 2
C9 C 0.4067(3) 0.41076(11) 0.60876(9) 0.0386(4) Uani 1 1 d . . . A 2
C10 C 0.4001(3) 0.47433(12) 0.66728(10) 0.0481(5) Uani 1 1 d . . . A 2
H10 H 0.2779 0.4745 0.6986 0.058 Uiso 1 1 calc R U . A 2
C11 C 0.5678(3) 0.53547(12) 0.67917(11) 0.0502(5) Uani 1 1 d . . . A 2
H11 H 0.5610 0.5784 0.7185 0.060 Uiso 1 1 calc R U . A 2
C12 C 0.7508(3) 0.53570(11) 0.63393(10) 0.0470(5) Uani 1 1 d . . . A 2
H12 H 0.8673 0.5785 0.6428 0.056 Uiso 1 1 calc R U . A 2
C13 C 0.7617(3) 0.47443(11) 0.57714(10) 0.0427(4) Uani 1 1 d . . . A 2
H13 H 0.8869 0.4745 0.5471 0.051 Uiso 1 1 calc R U . A 2
C14 C 0.5891(3) 0.41118(10) 0.56269(9) 0.0357(4) Uani 1 1 d . . . A 2
C15 C 0.6832(3) 0.12131(10) 0.58552(9) 0.0359(4) Uani 1 1 d . . . B 2
C16 C 0.7346(3) 0.18382(11) 0.64400(10) 0.0433(4) Uani 1 1 d . . . B 2
H16 H 0.8671 0.2191 0.6440 0.052 Uiso 1 1 calc R U . B 2
C17 C 0.5936(3) 0.19390(11) 0.70096(10) 0.0459(5) Uani 1 1 d . . . B 2
H17 H 0.6292 0.2360 0.7406 0.055 Uiso 1 1 calc R U . B 2
C18 C 0.3981(3) 0.14288(12) 0.70126(10) 0.0462(4) Uani 1 1 d . . . B 2
H18 H 0.3019 0.1502 0.7412 0.055 Uiso 1 1 calc R U . B 2
C19 C 0.3440(3) 0.08223(11) 0.64419(9) 0.0429(4) Uani 1 1 d . . . B 2
H19 H 0.2094 0.0483 0.6446 0.051 Uiso 1 1 calc R U . B 2
C20 C 0.4856(3) 0.06969(10) 0.58507(8) 0.0339(4) Uani 1 1 d . . . B 2
N1 N 0.5965(2) 0.35254(9) 0.50342(7) 0.0377(3) Uani 1 1 d . . . A 2
N2 N 0.2365(2) 0.34964(9) 0.59682(8) 0.0438(4) Uani 1 1 d . . . A 2
N3 N 0.848(5) 0.1135(12) 0.5316(11) 0.052(5) Uani 0.524(13) 1 d . U P C 1
C21 C 0.448(3) 0.0064(15) 0.5218(12) 0.026(2) Uani 0.524(13) 1 d . U P C 1
O2 O 0.816(4) 0.1111(9) 0.5293(10) 0.0375(19) Uani 0.476(13) 1 d . U P B 2
H2 H 0.7665 0.0697 0.5004 0.056 Uiso 0.476(13) 1 calc R U P C 2
N4 N 0.413(3) 0.0048(14) 0.5320(11) 0.030(3) Uani 0.476(13) 1 d . U P B 2
C22 C 0.7655(7) 0.0484(3) 0.4775(2) 0.0397(8) Uani 0.5 1 d . . P C 1
H22 H 0.8545 0.0380 0.4361 0.048 Uiso 0.5 1 calc R U P C 1
H1 H 0.7642 0.3376 0.4388 0.050 Uiso 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'
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'
H H 0.0000 0.0000 '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
C1 O1 H1 110.1 . .
O1 C1 C6 117.43(15) . .
O1 C1 C2 122.37(15) . .
C6 C1 C2 120.20(16) . .
C3 C2 C1 117.49(15) . .
C3 C2 C7 121.28(14) . .
C1 C2 C7 121.22(15) . .
C4 C3 C2 121.54(17) . .
C4 C3 H3 119.2 . .
C2 C3 H3 119.2 . .
C3 C4 C5 120.15(17) . .
C3 C4 H4 119.9 . .
C5 C4 H4 119.9 . .
C6 C5 C4 120.04(17) . .
C6 C5 H5 120.0 . .
C4 C5 H5 120.0 . .
C5 C6 C1 120.58(17) . .
C5 C6 H6 119.7 . .
C1 C6 H6 119.7 . .
N1 C7 C8 118.68(15) . .
N1 C7 C2 118.56(14) . .
C8 C7 C2 122.76(15) . .
N2 C8 C7 124.29(17) . .
N2 C8 H8 117.9 . .
C7 C8 H8 117.9 . .
N2 C9 C10 120.05(16) . .
N2 C9 C14 120.69(15) . .
C10 C9 C14 119.25(16) . .
C11 C10 C9 120.35(17) . .
C11 C10 H10 119.8 . .
C9 C10 H10 119.8 . .
C10 C11 C12 120.63(17) . .
C10 C11 H11 119.7 . .
C12 C11 H11 119.7 . .
C13 C12 C11 120.12(17) . .
C13 C12 H12 119.9 . .
C11 C12 H12 119.9 . .
C12 C13 C14 120.58(17) . .
C12 C13 H13 119.7 . .
C14 C13 H13 119.7 . .
N1 C14 C13 120.13(15) . .
N1 C14 C9 120.80(15) . .
C13 C14 C9 119.06(15) . .
O2 C15 C16 121.0(10) . .
O2 C15 C20 119.0(10) . .
C16 C15 C20 120.02(15) . .
C17 C16 C15 119.94(17) . .
C17 C16 H16 120.0 . .
C15 C16 H16 120.0 . .
C16 C17 C18 120.52(16) . .
C16 C17 H17 119.7 . .
C18 C17 H17 119.7 . .
C19 C18 C17 120.34(17) . .
C19 C18 H18 119.8 . .
C17 C18 H18 119.8 . .
C18 C19 C20 120.71(17) . .
C18 C19 H19 119.6 . .
C20 C19 H19 119.6 . .
N4 C20 C19 114.7(8) . .
N4 C20 C15 126.8(8) . .
C19 C20 C15 118.48(15) . .
C7 N1 C14 118.78(14) . .
C8 N2 C9 116.66(15) . .
C21 C21 C22 117(3) 3_656 3_656
C15 O2 H2 109.5 . .
C20 N4 N4 110.7(18) . 3_656
N3 C22 C21 127.5(13) . 3_656
N3 C22 H22 116.2 . .
C21 C22 H22 116.2 3_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.355(2) .
O1 H1 1.1219 .
C1 C6 1.393(2) .
C1 C2 1.417(2) .
C2 C3 1.402(2) .
C2 C7 1.465(2) .
C3 C4 1.375(2) .
C3 H3 0.9500 .
C4 C5 1.386(3) .
C4 H4 0.9500 .
C5 C6 1.374(3) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 N1 1.328(2) .
C7 C8 1.437(2) .
C8 N2 1.306(2) .
C8 H8 0.9500 .
C9 N2 1.371(2) .
C9 C10 1.409(2) .
C9 C14 1.410(2) .
C10 C11 1.361(3) .
C10 H10 0.9500 .
C11 C12 1.404(3) .
C11 H11 0.9500 .
C12 C13 1.366(2) .
C12 H12 0.9500 .
C13 C14 1.408(2) .
C13 H13 0.9500 .
C14 N1 1.369(2) .
C15 O2 1.328(19) .
C15 C16 1.406(2) .
C15 C20 1.409(2) .
C16 C17 1.370(3) .
C16 H16 0.9500 .
C17 C18 1.394(3) .
C17 H17 0.9500 .
C18 C19 1.372(2) .
C18 H18 0.9500 .
C19 C20 1.407(2) .
C19 H19 0.9500 .
C20 N4 1.39(2) .
N3 C22 1.42(2) .
C21 C21 1.04(5) 3_656
C21 C22 1.518(19) 3_656
O2 H2 0.8400 .
N4 N4 1.60(4) 3_656
C22 C21 1.52(2) 3_656
C22 H22 0.9500 .
