#------------------------------------------------------------------------------
#$Date: 2017-04-05 12:13:44 +0300 (Wed, 05 Apr 2017) $
#$Revision: 194955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/97/7119788.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_7119788
loop_
_publ_author_name
'Cheng, Xing'
'Zhu, Lei'
'Lin, Meijun'
'Chen, Jianxin'
'Huang, Xueliang'
_publ_section_title
;
 Rapid access to cyclopentadiene derivatives through gold-catalyzed
 cycloisomerization of ynamides with cyclopropenes by preferential
 activation of alkenes over alkynes.
;
_journal_issue                   26
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3745
_journal_page_last               3748
_journal_paper_doi               10.1039/c7cc01368j
_journal_volume                  53
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-12-30 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.73(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.0521(16)
_cell_length_b                   10.418(2)
_cell_length_c                   10.027(2)
_cell_measurement_reflns_used    2155
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4817
_cell_measurement_theta_min      2.8318
_cell_volume                     835.3(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '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  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6411
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.3(11)
_refine_ls_extinction_coef       0.035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3594
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0396
_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)+(0.0403P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0844
_reflns_number_gt                2677
_reflns_number_total             3594
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc01368j2.cif
_cod_data_source_block           d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_absolute_configuration' value ' unk ' changed to 'unk'
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.

'_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 

 Adding full bibliography for 7119788.cif.
;
_cod_original_cell_volume        835.4(3)
_cod_original_sg_symbol_H-M      'P2(1)   '
_cod_database_code               7119788
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
O1 O 0.39153(15) 0.65880(13) 0.00977(14) 0.0635(4) Uani 1 1 d .
N1 N 0.54586(14) 0.79875(12) 0.15424(12) 0.0384(3) Uani 1 1 d .
C1 C 0.40941(19) 0.75736(18) 0.07230(17) 0.0438(4) Uani 1 1 d .
O2 O 0.28684(13) 0.84690(13) 0.06830(13) 0.0561(4) Uani 1 1 d .
C2 C 0.3501(2) 0.9600(2) 0.1398(2) 0.0586(5) Uani 1 1 d .
H2A H 0.2728 0.9887 0.2009 0.070 Uiso 1 1 calc R
H2B H 0.3660 1.0289 0.0776 0.070 Uiso 1 1 calc R
C3 C 0.5141(2) 0.92147(19) 0.2162(2) 0.0564(5) Uani 1 1 d .
H3A H 0.6011 0.9833 0.2042 0.068 Uiso 1 1 calc R
H3B H 0.5049 0.9118 0.3112 0.068 Uiso 1 1 calc R
C4 C 0.69440(18) 0.72582(15) 0.17735(15) 0.0357(4) Uani 1 1 d .
C5 C 0.85923(19) 0.77403(16) 0.13390(15) 0.0390(4) Uani 1 1 d .
C6 C 0.8345(2) 0.8179(2) -0.01298(16) 0.0573(5) Uani 1 1 d .
H6A H 0.9389 0.8483 -0.0383 0.086 Uiso 1 1 calc R
H6B H 0.7535 0.8858 -0.0233 0.086 Uiso 1 1 calc R
H6C H 0.7957 0.7470 -0.0694 0.086 Uiso 1 1 calc R
C7 C 0.9615(2) 0.65388(18) 0.15147(18) 0.0475(4) Uani 1 1 d .
H7A H 1.0713 0.6468 0.1320 0.057 Uiso 1 1 calc R
C8 C 0.8752(2) 0.55873(17) 0.19849(17) 0.0469(4) Uani 1 1 d .
H8A H 0.9159 0.4762 0.2163 0.056 Uiso 1 1 calc R
C9 C 0.70637(19) 0.60219(16) 0.21836(15) 0.0387(4) Uani 1 1 d .
C10 C 0.58016(19) 0.52272(17) 0.27489(15) 0.0426(4) Uani 1 1 d .
C11 C 0.5775(2) 0.38995(19) 0.25916(18) 0.0572(5) Uani 1 1 d .
H11A H 0.6529 0.3508 0.2086 0.069 Uiso 1 1 calc R
C12 C 0.4634(3) 0.3157(2) 0.3181(2) 0.0792(8) Uani 1 1 d .
H12A H 0.4632 0.2270 0.3074 0.095 Uiso 1 1 calc R
C13 C 0.3503(3) 0.3726(3) 0.3926(3) 0.0878(8) Uani 1 1 d .
H13A H 0.2732 0.3227 0.4316 0.105 Uiso 1 1 calc R
C14 C 0.3519(3) 0.5013(3) 0.4087(2) 0.0777(7) Uani 1 1 d .
H14A H 0.2757 0.5396 0.4592 0.093 Uiso 1 1 calc R
C15 C 0.4646(2) 0.5765(2) 0.35133(18) 0.0580(5) Uani 1 1 d .
H15A H 0.4635 0.6649 0.3639 0.070 Uiso 1 1 calc R
C16 C 0.93562(17) 0.87990(15) 0.22905(15) 0.0381(4) Uani 1 1 d .
C17 C 0.9209(2) 1.00933(18) 0.20005(19) 0.0505(5) Uani 1 1 d .
H17A H 0.8653 1.0358 0.1181 0.061 Uiso 1 1 calc R
C18 C 0.9892(2) 1.1010(2) 0.2932(2) 0.0642(6) Uani 1 1 d .
H18A H 0.9765 1.1880 0.2735 0.077 Uiso 1 1 calc R
C19 C 1.0745(3) 1.0632(2) 0.4131(2) 0.0691(6) Uani 1 1 d .
H19A H 1.1206 1.1243 0.4742 0.083 Uiso 1 1 calc R
C20 C 1.0913(3) 0.9368(2) 0.4420(2) 0.0714(6) Uani 1 1 d .
H20A H 1.1500 0.9111 0.5230 0.086 Uiso 1 1 calc R
C21 C 1.0219(2) 0.8457(2) 0.35237(18) 0.0547(5) Uani 1 1 d .
H21A H 1.0332 0.7593 0.3749 0.066 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C4 122.41(14)
C1 N1 C3 111.41(13)
C4 N1 C3 126.13(13)
O1 C1 O2 122.00(14)
O1 C1 N1 128.55(16)
O2 C1 N1 109.45(16)
C1 O2 C2 109.55(12)
O2 C2 C3 105.88(15)
O2 C2 H2A 110.6
C3 C2 H2A 110.6
O2 C2 H2B 110.6
C3 C2 H2B 110.6
H2A C2 H2B 108.7
N1 C3 C2 101.84(14)
N1 C3 H3A 111.4
C2 C3 H3A 111.4
N1 C3 H3B 111.4
C2 C3 H3B 111.4
H3A C3 H3B 109.3
C9 C4 N1 126.22(14)
C9 C4 C5 111.48(13)
N1 C4 C5 121.52(14)
C7 C5 C4 100.12(13)
C7 C5 C6 111.71(15)
C4 C5 C6 110.64(12)
C7 C5 C16 110.60(13)
C4 C5 C16 110.85(13)
C6 C5 C16 112.30(14)
C5 C6 H6A 109.5
C5 C6 H6B 109.5
H6A C6 H6B 109.5
C5 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C8 C7 C5 111.22(15)
C8 C7 H7A 124.4
C5 C7 H7A 124.4
C7 C8 C9 110.44(15)
C7 C8 H8A 124.8
C9 C8 H8A 124.8
C4 C9 C8 106.65(14)
C4 C9 C10 128.61(15)
C8 C9 C10 124.73(15)
C15 C10 C11 117.40(17)
C15 C10 C9 121.42(16)
C11 C10 C9 121.11(17)
C12 C11 C10 120.6(2)
C12 C11 H11A 119.7
C10 C11 H11A 119.7
C13 C12 C11 120.3(2)
C13 C12 H12A 119.9
C11 C12 H12A 119.9
C14 C13 C12 119.6(2)
C14 C13 H13A 120.2
C12 C13 H13A 120.2
C13 C14 C15 120.9(3)
C13 C14 H14A 119.6
C15 C14 H14A 119.6
C14 C15 C10 121.2(2)
C14 C15 H15A 119.4
C10 C15 H15A 119.4
C17 C16 C21 117.29(16)
C17 C16 C5 123.42(14)
C21 C16 C5 119.27(15)
C16 C17 C18 120.49(18)
C16 C17 H17A 119.8
C18 C17 H17A 119.8
C19 C18 C17 120.4(2)
C19 C18 H18A 119.8
C17 C18 H18A 119.8
C20 C19 C18 119.70(19)
C20 C19 H19A 120.2
C18 C19 H19A 120.2
C19 C20 C21 120.5(2)
C19 C20 H20A 119.7
C21 C20 H20A 119.7
C20 C21 C16 121.62(19)
C20 C21 H21A 119.2
C16 C21 H21A 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.203(2)
N1 C1 1.3626(19)
N1 C4 1.4130(19)
N1 C3 1.457(2)
C1 O2 1.355(2)
O2 C2 1.441(2)
C2 C3 1.501(2)
C2 H2A 0.9700
C2 H2B 0.9700
C3 H3A 0.9700
C3 H3B 0.9700
C4 C9 1.352(2)
C4 C5 1.529(2)
C5 C7 1.497(2)
C5 C6 1.533(2)
C5 C16 1.539(2)
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 C8 1.329(3)
C7 H7A 0.9300
C8 C9 1.468(2)
C8 H8A 0.9300
C9 C10 1.475(2)
C10 C15 1.391(3)
C10 C11 1.392(2)
C11 C12 1.385(3)
C11 H11A 0.9300
C12 C13 1.378(4)
C12 H12A 0.9300
C13 C14 1.350(3)
C13 H13A 0.9300
C14 C15 1.375(3)
C14 H14A 0.9300
C15 H15A 0.9300
C16 C17 1.382(2)
C16 C21 1.392(2)
C17 C18 1.403(3)
C17 H17A 0.9300
C18 C19 1.370(3)
C18 H18A 0.9300
C19 C20 1.352(3)
C19 H19A 0.9300
C20 C21 1.379(3)
C20 H20A 0.9300
C21 H21A 0.9300
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
C4 N1 C1 O1 0.2(3)
C3 N1 C1 O1 -177.41(18)
C4 N1 C1 O2 -179.49(13)
C3 N1 C1 O2 2.91(19)
O1 C1 O2 C2 -173.38(17)
N1 C1 O2 C2 6.32(19)
C1 O2 C2 C3 -12.6(2)
C1 N1 C3 C2 -10.2(2)
C4 N1 C3 C2 172.31(15)
O2 C2 C3 N1 13.24(19)
C1 N1 C4 C9 -52.9(2)
C3 N1 C4 C9 124.36(18)
C1 N1 C4 C5 116.16(17)
C3 N1 C4 C5 -66.6(2)
C9 C4 C5 C7 2.69(16)
N1 C4 C5 C7 -167.82(13)
C9 C4 C5 C6 120.64(16)
N1 C4 C5 C6 -49.86(19)
C9 C4 C5 C16 -114.09(15)
N1 C4 C5 C16 75.41(17)
C4 C5 C7 C8 -1.49(17)
C6 C5 C7 C8 -118.65(16)
C16 C5 C7 C8 115.46(15)
C5 C7 C8 C9 -0.1(2)
N1 C4 C9 C8 167.14(14)
C5 C4 C9 C8 -2.82(16)
N1 C4 C9 C10 -13.9(3)
C5 C4 C9 C10 176.16(14)
C7 C8 C9 C4 1.83(19)
C7 C8 C9 C10 -177.21(15)
C4 C9 C10 C15 -31.3(2)
C8 C9 C10 C15 147.56(17)
C4 C9 C10 C11 151.89(17)
C8 C9 C10 C11 -29.3(2)
C15 C10 C11 C12 -0.1(3)
C9 C10 C11 C12 176.90(16)
C10 C11 C12 C13 0.4(3)
C11 C12 C13 C14 -0.5(3)
C12 C13 C14 C15 0.2(3)
C13 C14 C15 C10 0.1(3)
C11 C10 C15 C14 -0.2(3)
C9 C10 C15 C14 -177.14(17)
C7 C5 C16 C17 150.40(16)
C4 C5 C16 C17 -99.48(17)
C6 C5 C16 C17 24.9(2)
C7 C5 C16 C21 -30.8(2)
C4 C5 C16 C21 79.29(19)
C6 C5 C16 C21 -156.38(16)
C21 C16 C17 C18 -0.8(3)
C5 C16 C17 C18 177.98(15)
C16 C17 C18 C19 1.4(3)
C17 C18 C19 C20 -0.7(3)
C18 C19 C20 C21 -0.6(3)
C19 C20 C21 C16 1.2(3)
C17 C16 C21 C20 -0.4(3)
C5 C16 C21 C20 -179.29(17)
