#------------------------------------------------------------------------------
#$Date: 2017-08-04 08:52:13 +0300 (Fri, 04 Aug 2017) $
#$Revision: 199512 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/88/7228851.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_7228851
loop_
_publ_author_name
'Liu, Jiaming'
'Qian, Siran'
'Su, Zhenjie'
'Wang, Cunde'
_publ_section_title
;
 DBU-mediated [4 + 2] annulations of donor--acceptor cyclopropanes with
 3-aryl-2-cyanoacrylates for the synthesis of fully substituted anilines
;
_journal_issue                   61
_journal_name_full               'RSC Adv.'
_journal_page_first              38342
_journal_paper_doi               10.1039/C7RA07230A
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C28 H18 Cl N3 O2'
_chemical_formula_sum            'C28 H18 Cl N3 O2'
_chemical_formula_weight         463.90
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-05-04 deposited with the CCDC.
2017-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.948(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.579(3)
_cell_length_b                   12.312(3)
_cell_length_c                   17.454(4)
_cell_measurement_reflns_used    5381
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      2.50
_cell_volume                     2367.2(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11690
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.192
_exptl_crystal_colour            cololess
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0515P)²+0.7546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1299
_reflns_number_gt                3763
_reflns_number_total             5391
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ra07230a2.cif
_cod_data_source_block           001_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        2367.0(11)
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               7228851
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.44098(6) 1.11692(6) 0.11036(5) 0.0953(3) Uani 1 1 d .
C3 C 0.90379(14) 0.61531(13) 0.30386(10) 0.0333(4) Uani 1 1 d .
C22 C 0.72293(15) 0.87514(12) 0.24491(10) 0.0344(4) Uani 1 1 d .
C4 C 0.81953(14) 0.68936(13) 0.25722(10) 0.0328(4) Uani 1 1 d .
C16 C 0.73824(15) 0.66286(13) 0.17438(10) 0.0347(4) Uani 1 1 d .
C10 C 0.85436(14) 0.41022(13) 0.28925(10) 0.0350(4) Uani 1 1 d .
N1 N 1.05008(16) 0.77126(13) 0.48900(9) 0.0599(5) Uani 1 1 d .
H1A H 1.1011 0.7243 0.5166 0.072 Uiso 1 1 calc R
H1B H 1.0464 0.8349 0.5084 0.072 Uiso 1 1 calc R
C2 C 0.97874(15) 0.64169(13) 0.38124(10) 0.0365(4) Uani 1 1 d .
O1 O 0.99413(14) 0.49535(11) 0.23436(10) 0.0613(4) Uani 1 1 d .
C5 C 0.81325(14) 0.79242(12) 0.29015(10) 0.0327(4) Uani 1 1 d .
C9 C 0.92158(15) 0.50442(13) 0.27159(10) 0.0368(4) Uani 1 1 d .
C11 C 0.77106(15) 0.42179(14) 0.33149(11) 0.0422(4) Uani 1 1 d .
H11 H 0.7563 0.4900 0.3494 0.051 Uiso 1 1 calc R
O2 O 0.51834(16) 0.62154(13) -0.06292(8) 0.0736(5) Uani 1 1 d .
C27 C 0.63355(16) 0.91097(14) 0.27696(11) 0.0421(4) Uani 1 1 d .
H27 H 0.6317 0.8847 0.3265 0.050 Uiso 1 1 calc R
C14 C 0.8169(2) 0.21819(15) 0.28056(14) 0.0595(6) Uani 1 1 d .
H14 H 0.8326 0.1494 0.2641 0.071 Uiso 1 1 calc R
C6 C 0.89106(15) 0.81941(13) 0.36682(10) 0.0352(4) Uani 1 1 d .
N3 N 0.89222(16) 1.01245(13) 0.42347(10) 0.0578(5) Uani 1 1 d .
C21 C 0.61255(16) 0.66663(14) 0.15651(10) 0.0395(4) Uani 1 1 d .
H21 H 0.5792 0.6786 0.1979 0.047 Uiso 1 1 calc R
C1 C 0.97538(15) 0.74490(14) 0.41494(10) 0.0390(4) Uani 1 1 d .
C23 C 0.72519(16) 0.91530(15) 0.17118(11) 0.0441(4) Uani 1 1 d .
H23 H 0.7848 0.8919 0.1494 0.053 Uiso 1 1 calc R
C8 C 0.88994(16) 0.92790(14) 0.39692(10) 0.0414(4) Uani 1 1 d .
C25 C 0.55077(17) 1.02403(15) 0.16294(13) 0.0527(5) Uani 1 1 d .
N2 N 1.13342(19) 0.50403(16) 0.46693(11) 0.0703(6) Uani 1 1 d .
C26 C 0.54731(17) 0.98552(15) 0.23560(13) 0.0495(5) Uani 1 1 d .
H26 H 0.4875 1.0092 0.2571 0.059 Uiso 1 1 calc R
C7 C 1.06444(17) 0.56394(15) 0.42806(11) 0.0460(4) Uani 1 1 d .
C20 C 0.53550(17) 0.65293(15) 0.07826(11) 0.0467(4) Uani 1 1 d .
H20 H 0.4518 0.6556 0.0677 0.056 Uiso 1 1 calc R
C15 C 0.87742(18) 0.30723(14) 0.26411(12) 0.0494(5) Uani 1 1 d .
H15 H 0.9336 0.2986 0.2363 0.059 Uiso 1 1 calc R
C13 C 0.73297(19) 0.23085(16) 0.32142(13) 0.0577(6) Uani 1 1 d .
H13 H 0.6917 0.1705 0.3317 0.069 Uiso 1 1 calc R
C17 C 0.78511(18) 0.64247(17) 0.11141(11) 0.0511(5) Uani 1 1 d .
H17 H 0.8687 0.6376 0.1218 0.061 Uiso 1 1 calc R
C19 C 0.58431(19) 0.63546(16) 0.01673(11) 0.0511(5) Uani 1 1 d .
C12 C 0.70976(18) 0.33135(16) 0.34697(13) 0.0539(5) Uani 1 1 d .
H12 H 0.6532 0.3391 0.3746 0.065 Uiso 1 1 calc R
C24 C 0.63905(19) 0.99019(16) 0.12972(13) 0.0547(5) Uani 1 1 d .
H24 H 0.6405 1.0173 0.0803 0.066 Uiso 1 1 calc R
C18 C 0.7091(2) 0.6294(2) 0.03378(12) 0.0618(6) Uani 1 1 d .
H18 H 0.7421 0.6163 -0.0077 0.074 Uiso 1 1 calc R
C28 C 0.3923(2) 0.6423(2) -0.08670(15) 0.0876(9) Uani 1 1 d .
H28A H 0.3536 0.5914 -0.0608 0.131 Uiso 1 1 calc R
H28B H 0.3592 0.6347 -0.1441 0.131 Uiso 1 1 calc R
H28C H 0.3783 0.7148 -0.0714 0.131 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'
Cl Cl 0.1484 0.1585 '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
C2 C3 C4 121.61(14)
C2 C3 C9 116.92(14)
C4 C3 C9 121.42(14)
C23 C22 C27 119.29(16)
C23 C22 C5 121.45(15)
C27 C22 C5 119.25(15)
C3 C4 C5 117.75(14)
C3 C4 C16 122.54(14)
C5 C4 C16 119.71(14)
C17 C16 C21 117.69(16)
C17 C16 C4 121.34(15)
C21 C16 C4 120.76(15)
C11 C10 C15 119.44(17)
C11 C10 C9 121.68(15)
C15 C10 C9 118.87(16)
C3 C2 C1 121.63(15)
C3 C2 C7 120.51(15)
C1 C2 C7 117.84(15)
C6 C5 C4 120.35(15)
C6 C5 C22 118.69(14)
C4 C5 C22 120.95(14)
O1 C9 C10 122.25(15)
O1 C9 C3 118.50(15)
C10 C9 C3 119.20(14)
C12 C11 C10 120.00(17)
C19 O2 C28 118.45(19)
C26 C27 C22 120.47(17)
C15 C14 C13 120.14(18)
C5 C6 C1 122.42(14)
C5 C6 C8 119.56(15)
C1 C6 C8 117.96(15)
C20 C21 C16 121.69(16)
N1 C1 C2 121.60(16)
N1 C1 C6 122.20(15)
C2 C1 C6 116.20(15)
C24 C23 C22 120.35(18)
N3 C8 C6 177.34(19)
C26 C25 C24 121.37(18)
C26 C25 Cl1 119.38(17)
C24 C25 Cl1 119.25(17)
C25 C26 C27 119.44(18)
N2 C7 C2 178.2(2)
C19 C20 C21 119.43(18)
C14 C15 C10 119.92(19)
C12 C13 C14 120.69(19)
C18 C17 C16 120.76(18)
O2 C19 C20 125.08(19)
O2 C19 C18 115.36(18)
C20 C19 C18 119.55(17)
C13 C12 C11 119.8(2)
C23 C24 C25 119.09(19)
C17 C18 C19 120.84(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C25 1.746(2)
C3 C2 1.400(2)
C3 C4 1.399(2)
C3 C9 1.515(2)
C22 C23 1.386(2)
C22 C27 1.391(2)
C22 C5 1.498(2)
C4 C5 1.404(2)
C4 C16 1.498(2)
C16 C17 1.390(2)
C16 C21 1.392(2)
C10 C11 1.390(2)
C10 C15 1.394(2)
C10 C9 1.481(2)
N1 C1 1.355(2)
C2 C1 1.406(2)
C2 C7 1.438(2)
O1 C9 1.215(2)
C5 C6 1.404(2)
C11 C12 1.391(3)
O2 C19 1.375(2)
O2 C28 1.413(3)
C27 C26 1.384(3)
C14 C15 1.378(3)
C14 C13 1.380(3)
C6 C1 1.412(2)
C6 C8 1.437(2)
N3 C8 1.137(2)
C21 C20 1.392(2)
C23 C24 1.387(3)
C25 C26 1.366(3)
C25 C24 1.386(3)
N2 C7 1.144(2)
C20 C19 1.376(3)
C13 C12 1.370(3)
C17 C18 1.379(3)
C19 C18 1.384(3)
