#------------------------------------------------------------------------------
#$Date: 2020-09-06 11:27:21 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256002 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/67/7126784.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_7126784
loop_
_publ_author_name
'Babu, Kaki Raveendra'
'Li, Yang'
'Xu, Wenbo'
'Tang, Yuhai'
'Zhang, Wenquan'
'Xu, Silong'
_publ_section_title
;
 Multicomponent benzannulation of allylic P-ylides with isocyanates or
 aldehydes for construction of anilines and biaryls.
;
_journal_issue                   62
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8865
_journal_page_last               8868
_journal_paper_doi               10.1039/d0cc03461d
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C22 H25 N O6'
_chemical_formula_sum            'C22 H25 N O6'
_chemical_formula_weight         399.43
_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   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-12-27 deposited with the CCDC.	2020-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.712(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0462(17)
_cell_length_b                   14.645(2)
_cell_length_c                   13.553(2)
_cell_measurement_reflns_used    6845
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.47
_cell_measurement_theta_min      2.38
_cell_volume                     2088.6(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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  0.0297
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22029
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.554
_diffrn_reflns_theta_min         2.092
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       LUMP
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0409
_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)+(0.0492P)²+0.9434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1130
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3408
_reflns_number_total             4320
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc03461d2.cif
_cod_data_source_block           mo_Hexin_20181228_1_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7126784.cif.
;
_cod_original_cell_volume        2088.6(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7126784
_shelx_shelxl_version_number     2016/6
_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   0.988
_shelx_estimated_absorpt_t_max   0.991
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
O6 O 0.82678(9) 0.05900(7) 0.80658(8) 0.0295(3) Uani 1 1 d . . . . .
O5 O 0.73704(11) 0.19490(7) 0.75239(9) 0.0351(3) Uani 1 1 d . . . . .
C5 C 0.67101(14) -0.04539(10) 0.64228(11) 0.0268(3) Uani 1 1 d . . . . .
C20 C 0.73017(14) 0.11807(10) 0.78237(11) 0.0265(3) Uani 1 1 d . . . . .
C21 C 0.93982(15) 0.08778(12) 0.78080(13) 0.0357(4) Uani 1 1 d . . . . .
H21A H 0.971321 0.145160 0.814693 0.043 Uiso 1 1 calc R U . . .
H21B H 0.920197 0.096016 0.706573 0.043 Uiso 1 1 calc R U . . .
C22 C 1.03759(16) 0.01398(13) 0.81784(14) 0.0421(4) Uani 1 1 d . . . . .
H22A H 1.113784 0.030590 0.802151 0.063 Uiso 1 1 calc R U . . .
H22B H 1.056181 0.006558 0.891332 0.063 Uiso 1 1 calc R U . . .
H22C H 1.005296 -0.042357 0.783717 0.063 Uiso 1 1 calc R U . . .
C11 C 0.45876(14) 0.11081(10) 0.89364(11) 0.0259(3) Uani 1 1 d . . . . .
C12 C 0.55862(14) 0.13857(10) 0.85809(11) 0.0264(3) Uani 1 1 d . . . . .
H12 H 0.588757 0.198041 0.871183 0.032 Uiso 1 1 calc R U . . .
C10 C 0.41603(13) 0.02159(10) 0.87493(11) 0.0253(3) Uani 1 1 d . . . . .
H10 H 0.352310 0.001275 0.901319 0.030 Uiso 1 1 calc R U . . .
C9 C 0.46597(13) -0.03848(10) 0.81765(11) 0.0254(3) Uani 1 1 d . . . . .
C13 C 0.61461(14) 0.08068(10) 0.80388(11) 0.0256(3) Uani 1 1 d . . . . .
C8 C 0.56575(13) -0.00930(10) 0.77739(11) 0.0250(3) Uani 1 1 d . . . . .
C14 C 0.41369(14) -0.13250(10) 0.79751(12) 0.0292(3) Uani 1 1 d . . . . .
O2 O 0.31867(10) -0.14745(7) 0.83749(9) 0.0326(3) Uani 1 1 d . . . . .
O1 O 0.45060(12) -0.19110(8) 0.74971(10) 0.0426(3) Uani 1 1 d . . . . .
C15 C 0.26763(17) -0.23978(11) 0.82559(14) 0.0387(4) Uani 1 1 d . . . . .
H15A H 0.332045 -0.282675 0.863305 0.046 Uiso 1 1 calc R U . . .
H15B H 0.240228 -0.257079 0.753067 0.046 Uiso 1 1 calc R U . . .
C16 C 0.15696(18) -0.24057(13) 0.86790(17) 0.0478(5) Uani 1 1 d . . . . .
H16A H 0.120945 -0.300767 0.861194 0.072 Uiso 1 1 calc R U . . .
H16B H 0.185258 -0.223472 0.939673 0.072 Uiso 1 1 calc R U . . .
H16C H 0.093845 -0.197989 0.829922 0.072 Uiso 1 1 calc R U . . .
C17 C 0.40531(15) 0.17769(11) 0.95156(12) 0.0298(3) Uani 1 1 d . . . . .
O3 O 0.30962(10) 0.14319(7) 0.98125(9) 0.0328(3) Uani 1 1 d . . . . .
O4 O 0.44281(13) 0.25533(8) 0.96879(11) 0.0468(3) Uani 1 1 d . . . . .
C18 C 0.25158(19) 0.20603(12) 1.03723(16) 0.0443(4) Uani 1 1 d . . . . .
H18A H 0.221305 0.260114 0.995750 0.053 Uiso 1 1 calc R U . . .
H18B H 0.313691 0.224699 1.101512 0.053 Uiso 1 1 calc R U . . .
C19 C 0.14330(17) 0.15840(14) 1.05939(15) 0.0457(5) Uani 1 1 d . . . . .
H19A H 0.104000 0.198879 1.096258 0.069 Uiso 1 1 calc R U . . .
H19B H 0.082085 0.140484 0.995387 0.069 Uiso 1 1 calc R U . . .
H19C H 0.174144 0.105195 1.100776 0.069 Uiso 1 1 calc R U . . .
N1 N 0.61048(12) -0.06708(9) 0.71805(10) 0.0296(3) Uani 1 1 d . . . . .
H1 H 0.600888 -0.124332 0.727639 0.036 Uiso 1 1 calc R U . . .
C4 C 0.76316(15) -0.10503(10) 0.62948(12) 0.0300(3) Uani 1 1 d . . . . .
H4 H 0.787297 -0.155418 0.672798 0.036 Uiso 1 1 calc R U . . .
C2 C 0.78428(15) -0.01485(11) 0.48583(12) 0.0308(3) Uani 1 1 d . . . . .
C6 C 0.63519(14) 0.02940(10) 0.57684(12) 0.0295(3) Uani 1 1 d . . . . .
H6 H 0.573677 0.069640 0.584761 0.035 Uiso 1 1 calc R U . . .
C7 C 0.69155(15) 0.04381(10) 0.49959(12) 0.0306(3) Uani 1 1 d . . . . .
H7 H 0.666777 0.093907 0.455917 0.037 Uiso 1 1 calc R U . . .
C3 C 0.81902(15) -0.08943(11) 0.55225(12) 0.0318(3) Uani 1 1 d . . . . .
H3 H 0.880856 -0.129525 0.544630 0.038 Uiso 1 1 calc R U . . .
C1 C 0.84261(17) 0.00058(13) 0.39981(13) 0.0415(4) Uani 1 1 d . . . . .
H1A H 0.904302 -0.046194 0.402114 0.062 Uiso 1 1 calc R U . . .
H1B H 0.777315 -0.001500 0.334204 0.062 Uiso 1 1 calc R U . . .
H1C H 0.883291 0.059242 0.408456 0.062 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 0.0033 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
_geom_angle_publ_flag
C20 O6 C21 115.64(12) . . ?
C6 C5 C4 119.50(14) . . ?
C6 C5 N1 122.17(13) . . ?
C4 C5 N1 118.19(13) . . ?
O5 C20 O6 124.03(14) . . ?
O5 C20 C13 123.47(14) . . ?
O6 C20 C13 112.36(12) . . ?
O6 C21 C22 107.04(13) . . ?
O6 C21 H21A 110.3 . . ?
C22 C21 H21A 110.3 . . ?
O6 C21 H21B 110.3 . . ?
C22 C21 H21B 110.3 . . ?
H21A C21 H21B 108.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C11 C12 118.27(13) . . ?
C10 C11 C17 123.38(13) . . ?
C12 C11 C17 118.33(13) . . ?
C13 C12 C11 122.26(14) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C11 C10 C9 121.77(14) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C9 C8 120.25(13) . . ?
C10 C9 C14 119.32(13) . . ?
C8 C9 C14 120.43(13) . . ?
C12 C13 C8 120.18(13) . . ?
C12 C13 C20 115.11(13) . . ?
C8 C13 C20 124.62(13) . . ?
N1 C8 C13 123.06(13) . . ?
N1 C8 C9 119.92(13) . . ?
C13 C8 C9 117.02(13) . . ?
O1 C14 O2 122.09(14) . . ?
O1 C14 C9 125.19(14) . . ?
O2 C14 C9 112.72(13) . . ?
C14 O2 C15 115.63(12) . . ?
O2 C15 C16 107.35(14) . . ?
O2 C15 H15A 110.2 . . ?
C16 C15 H15A 110.2 . . ?
O2 C15 H15B 110.2 . . ?
C16 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 O3 123.54(14) . . ?
O4 C17 C11 123.69(14) . . ?
O3 C17 C11 112.77(13) . . ?
C17 O3 C18 115.47(12) . . ?
O3 C18 C19 108.41(14) . . ?
O3 C18 H18A 110.0 . . ?
C19 C18 H18A 110.0 . . ?
O3 C18 H18B 110.0 . . ?
C19 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C8 N1 C5 128.59(13) . . ?
C8 N1 H1 115.7 . . ?
C5 N1 H1 115.7 . . ?
C3 C4 C5 120.07(14) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C7 C2 C3 117.81(14) . . ?
C7 C2 C1 121.00(15) . . ?
C3 C2 C1 121.18(15) . . ?
C7 C6 C5 119.72(14) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C2 121.64(15) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
C4 C3 C2 121.26(14) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
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 . . ?
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
O6 C20 1.3349(18) . ?
O6 C21 1.4575(18) . ?
O5 C20 1.2065(18) . ?
C5 C6 1.389(2) . ?
C5 C4 1.392(2) . ?
C5 N1 1.4213(19) . ?
C20 C13 1.497(2) . ?
C21 C22 1.502(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C11 C10 1.386(2) . ?
C11 C12 1.392(2) . ?
C11 C17 1.485(2) . ?
C12 C13 1.385(2) . ?
C12 H12 0.9300 . ?
C10 C9 1.393(2) . ?
C10 H10 0.9300 . ?
C9 C8 1.436(2) . ?
C9 C14 1.486(2) . ?
C13 C8 1.428(2) . ?
C8 N1 1.3596(18) . ?
C14 O1 1.2178(19) . ?
C14 O2 1.3376(18) . ?
O2 C15 1.4549(19) . ?
C15 C16 1.500(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O4 1.2084(19) . ?
C17 O3 1.3392(18) . ?
O3 C18 1.4593(18) . ?
C18 C19 1.492(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N1 H1 0.8600 . ?
C4 C3 1.386(2) . ?
C4 H4 0.9300 . ?
C2 C7 1.392(2) . ?
C2 C3 1.393(2) . ?
C2 C1 1.511(2) . ?
C6 C7 1.387(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 O6 C20 O5 -8.5(2) . . . . ?
C21 O6 C20 C13 175.69(12) . . . . ?
C20 O6 C21 C22 177.84(13) . . . . ?
C10 C11 C12 C13 0.9(2) . . . . ?
C17 C11 C12 C13 179.69(13) . . . . ?
C12 C11 C10 C9 -3.2(2) . . . . ?
C17 C11 C10 C9 178.09(14) . . . . ?
C11 C10 C9 C8 1.0(2) . . . . ?
C11 C10 C9 C14 -178.21(13) . . . . ?
C11 C12 C13 C8 3.6(2) . . . . ?
C11 C12 C13 C20 -173.16(13) . . . . ?
O5 C20 C13 C12 -44.1(2) . . . . ?
O6 C20 C13 C12 131.76(13) . . . . ?
O5 C20 C13 C8 139.28(16) . . . . ?
O6 C20 C13 C8 -44.84(19) . . . . ?
C12 C13 C8 N1 175.17(14) . . . . ?
C20 C13 C8 N1 -8.4(2) . . . . ?
C12 C13 C8 C9 -5.7(2) . . . . ?
C20 C13 C8 C9 170.75(13) . . . . ?
C10 C9 C8 N1 -177.35(13) . . . . ?
C14 C9 C8 N1 1.8(2) . . . . ?
C10 C9 C8 C13 3.5(2) . . . . ?
C14 C9 C8 C13 -177.36(13) . . . . ?
C10 C9 C14 O1 -179.07(15) . . . . ?
C8 C9 C14 O1 1.8(2) . . . . ?
C10 C9 C14 O2 1.3(2) . . . . ?
C8 C9 C14 O2 -177.90(13) . . . . ?
O1 C14 O2 C15 3.6(2) . . . . ?
C9 C14 O2 C15 -176.75(13) . . . . ?
C14 O2 C15 C16 -175.86(14) . . . . ?
C10 C11 C17 O4 179.42(16) . . . . ?
C12 C11 C17 O4 0.7(2) . . . . ?
C10 C11 C17 O3 -1.6(2) . . . . ?
C12 C11 C17 O3 179.73(13) . . . . ?
O4 C17 O3 C18 -0.1(2) . . . . ?
C11 C17 O3 C18 -179.09(14) . . . . ?
C17 O3 C18 C19 177.10(14) . . . . ?
C13 C8 N1 C5 -25.8(2) . . . . ?
C9 C8 N1 C5 155.06(15) . . . . ?
C6 C5 N1 C8 -36.9(2) . . . . ?
C4 C5 N1 C8 147.48(15) . . . . ?
C6 C5 C4 C3 0.3(2) . . . . ?
N1 C5 C4 C3 176.08(14) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
N1 C5 C6 C7 -175.60(14) . . . . ?
C5 C6 C7 C2 -0.3(2) . . . . ?
C3 C2 C7 C6 0.2(2) . . . . ?
C1 C2 C7 C6 178.60(15) . . . . ?
C5 C4 C3 C2 -0.4(2) . . . . ?
C7 C2 C3 C4 0.1(2) . . . . ?
C1 C2 C3 C4 -178.28(15) . . . . ?
