#------------------------------------------------------------------------------
#$Date: 2019-11-28 21:19:05 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244650 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/93/7239321.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_7239321
loop_
_publ_author_name
'Li, Jian'
'Ding, Dong'
'Liu, Li'
'Sun, Jiangtao'
_publ_section_title
;
 CuI-catalyzed cross-coupling of diazoacetamide with terminal alkynes: an
 approach to synthesizing substituted dienamides and 3-butynamides
;
_journal_issue                   44
_journal_name_full               'RSC Advances'
_journal_page_first              21260
_journal_paper_doi               10.1039/c3ra44801k
_journal_volume                  3
_journal_year                    2013
_chemical_formula_sum            'C16 H12 Cl N O'
_chemical_formula_weight         269.72
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 94.85(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.882(5)
_cell_length_b                   28.92(3)
_cell_length_c                   9.203(10)
_cell_measurement_reflns_used    1350
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.76
_cell_measurement_theta_min      2.33
_cell_volume                     1295(2)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0728
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7853
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.9479
_exptl_absorpt_correction_T_min  0.9296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.832
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2585
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.832
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0466
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1553
_reflns_number_gt                1490
_reflns_number_total             2585
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra44801k.txt
_cod_data_source_block           130407h
_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/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1294(2)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7239321
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
C1 C 1.1098(5) 0.62707(9) 0.9186(3) 0.0565(7) Uani 1 1 d .
C2 C 1.1135(5) 0.58916(9) 0.8297(3) 0.0502(6) Uani 1 1 d .
H2 H 1.2294 0.5886 0.7546 0.060 Uiso 1 1 calc R
C3 C 0.9464(4) 0.55202(8) 0.8512(3) 0.0444(6) Uani 1 1 d .
C4 C 0.7814(5) 0.55327(10) 0.9640(3) 0.0555(7) Uani 1 1 d .
H4 H 0.6677 0.5283 0.9805 0.067 Uiso 1 1 calc R
C5 C 0.7839(6) 0.59130(11) 1.0526(3) 0.0660(8) Uani 1 1 d .
H5 H 0.6724 0.5917 1.1297 0.079 Uiso 1 1 calc R
C6 C 0.9450(6) 0.62849(11) 1.0307(3) 0.0638(8) Uani 1 1 d .
H6 H 0.9428 0.6543 1.0909 0.077 Uiso 1 1 calc R
C7 C 0.7474(5) 0.48765(8) 0.7061(3) 0.0451(6) Uani 1 1 d .
C8 C 0.8212(5) 0.45022(9) 0.6094(3) 0.0533(7) Uani 1 1 d .
H8 H 1.0044 0.4466 0.5910 0.064 Uiso 1 1 calc R
C9 C 0.6418(5) 0.42223(9) 0.5490(3) 0.0528(7) Uani 1 1 d .
C10 C 0.4598(5) 0.39446(9) 0.4890(3) 0.0534(7) Uani 1 1 d .
H10 H 0.3720 0.4035 0.4000 0.064 Uiso 1 1 calc R
C11 C 0.3781(5) 0.35006(9) 0.5475(3) 0.0498(6) Uani 1 1 d .
C12 C 0.1697(6) 0.32531(11) 0.4759(3) 0.0712(9) Uani 1 1 d .
H12 H 0.0800 0.3372 0.3909 0.085 Uiso 1 1 calc R
C13 C 0.0912(7) 0.28362(12) 0.5265(4) 0.0837(10) Uani 1 1 d .
H13 H -0.0500 0.2672 0.4755 0.100 Uiso 1 1 calc R
C14 C 0.2169(7) 0.26579(11) 0.6504(4) 0.0774(9) Uani 1 1 d .
H14 H 0.1629 0.2372 0.6846 0.093 Uiso 1 1 calc R
C15 C 0.4221(7) 0.28982(11) 0.7249(4) 0.0758(9) Uani 1 1 d .
H15 H 0.5079 0.2779 0.8109 0.091 Uiso 1 1 calc R
C16 C 0.5029(6) 0.33159(10) 0.6732(3) 0.0658(8) Uani 1 1 d .
H16 H 0.6450 0.3477 0.7243 0.079 Uiso 1 1 calc R
Cl1 Cl 1.31310(17) 0.67371(3) 0.88605(10) 0.0819(3) Uani 1 1 d .
N1 N 0.9583(4) 0.51395(7) 0.7577(2) 0.0465(5) Uani 1 1 d .
H1 H 1.1175 0.5068 0.7310 0.056 Uiso 1 1 calc R
O1 O 0.5143(3) 0.49449(6) 0.7343(2) 0.0625(5) Uani 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'
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
C6 C1 C2 121.0(3)
C6 C1 Cl1 119.7(2)
C2 C1 Cl1 119.2(2)
C1 C2 C3 120.2(3)
C1 C2 H2 119.9
C3 C2 H2 119.9
C4 C3 C2 118.9(2)
C4 C3 N1 123.0(2)
C2 C3 N1 118.1(2)
C3 C4 C5 119.8(3)
C3 C4 H4 120.1
C5 C4 H4 120.1
C6 C5 C4 121.7(3)
C6 C5 H5 119.2
C4 C5 H5 119.2
C5 C6 C1 118.4(3)
C5 C6 H6 120.8
C1 C6 H6 120.8
O1 C7 N1 122.9(2)
O1 C7 C8 122.5(2)
N1 C7 C8 114.5(2)
C9 C8 C7 122.3(2)
C9 C8 H8 118.8
C7 C8 H8 118.8
C8 C9 C10 179.3(3)
C9 C10 C11 126.2(3)
C9 C10 H10 116.9
C11 C10 H10 116.9
C12 C11 C16 117.6(3)
C12 C11 C10 119.9(2)
C16 C11 C10 122.6(2)
C13 C12 C11 121.3(3)
C13 C12 H12 119.4
C11 C12 H12 119.4
C14 C13 C12 120.4(3)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C15 119.6(3)
C13 C14 H14 120.2
C15 C14 H14 120.2
C14 C15 C16 119.9(3)
C14 C15 H15 120.0
C16 C15 H15 120.0
C15 C16 C11 121.2(3)
C15 C16 H16 119.4
C11 C16 H16 119.4
C7 N1 C3 126.6(2)
C7 N1 H1 116.7
C3 N1 H1 116.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.362(4)
C1 C2 1.369(4)
C1 Cl1 1.716(3)
C2 C3 1.373(3)
C2 H2 0.9300
C3 C4 1.367(4)
C3 N1 1.401(3)
C4 C5 1.368(4)
C4 H4 0.9300
C5 C6 1.357(4)
C5 H5 0.9300
C6 H6 0.9300
C7 O1 1.205(3)
C7 N1 1.335(3)
C7 C8 1.465(4)
C8 C9 1.284(4)
C8 H8 0.9300
C9 C10 1.287(4)
C10 C11 1.461(4)
C10 H10 0.9300
C11 C12 1.367(4)
C11 C16 1.369(4)
C12 C13 1.359(4)
C12 H12 0.9300
C13 C14 1.351(5)
C13 H13 0.9300
C14 C15 1.356(4)
C14 H14 0.9300
C15 C16 1.368(4)
C15 H15 0.9300
C16 H16 0.9300
N1 H1 0.8600
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
C6 C1 C2 C3 1.0(4)
Cl1 C1 C2 C3 -178.07(17)
C1 C2 C3 C4 -1.2(3)
C1 C2 C3 N1 -179.8(2)
C2 C3 C4 C5 0.4(3)
N1 C3 C4 C5 178.8(2)
C3 C4 C5 C6 0.7(4)
C4 C5 C6 C1 -0.9(4)
C2 C1 C6 C5 0.1(4)
Cl1 C1 C6 C5 179.2(2)
O1 C7 C8 C9 -0.3(4)
N1 C7 C8 C9 -179.0(2)
C7 C8 C9 C10 11(31)
C8 C9 C10 C11 -103(31)
C9 C10 C11 C12 176.2(3)
C9 C10 C11 C16 -3.9(4)
C16 C11 C12 C13 -0.7(5)
C10 C11 C12 C13 179.2(3)
C11 C12 C13 C14 0.6(5)
C12 C13 C14 C15 0.2(6)
C13 C14 C15 C16 -0.8(5)
C14 C15 C16 C11 0.6(5)
C12 C11 C16 C15 0.1(4)
C10 C11 C16 C15 -179.8(3)
O1 C7 N1 C3 0.9(4)
C8 C7 N1 C3 179.6(2)
C4 C3 N1 C7 38.8(3)
C2 C3 N1 C7 -142.7(2)
