#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:58:28 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180242 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/28/7112893.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_7112893
loop_
_publ_author_name
'Yan, Xiaoyu'
'Zhou, Yiqing'
'Xi, Chanjuan'
_publ_section_title
;
 Reactivity of alkynylzirconates towards allyl bromides: selective
 formation of β-allyl-zirconacyclopentadienes.
;
_journal_issue                   41
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7801
_journal_page_last               7803
_journal_paper_doi               10.1039/c0cc02997a
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C26 H20 N4'
_chemical_formula_weight         388.46
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.96(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.132(2)
_cell_length_b                   9.6628(19)
_cell_length_c                   20.142(4)
_cell_measurement_reflns_used    7204
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4824
_cell_measurement_theta_min      1.0123
_cell_volume                     2163.7(7)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17162
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_correction_T_min  0.9773
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.014
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.1343
_refine_ls_R_factor_gt           0.1249
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1352P)²+2.9805P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3168
_refine_ls_wR_factor_ref         0.3267
_reflns_number_gt                4592
_reflns_number_total             4958
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0cc02997a.txt
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_exptl_absorpt_correction_type' value 'Numerical'
changed to 'numerical' according to
/usr/data/users/saulius/automatic-downloads/retrospective/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7112893
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N4 N 0.7204(3) 0.5149(3) 0.23607(15) 0.0474(8) Uani 1 1 d .
C5 C 0.5588(3) 0.7410(3) 0.10573(17) 0.0382(7) Uani 1 1 d .
H5A H 0.5229 0.7670 0.0609 0.046 Uiso 1 1 calc R
C11 C 0.6925(3) 0.7221(3) 0.09527(16) 0.0353(7) Uani 1 1 d .
C4 C 0.5297(3) 0.8613(3) 0.15027(17) 0.0370(7) Uani 1 1 d .
C24 C 0.5272(3) 0.4847(4) 0.0915(2) 0.0447(8) Uani 1 1 d .
C9 C 0.4794(3) 0.8511(4) 0.20825(17) 0.0397(7) Uani 1 1 d .
C8 C 0.4491(3) 0.7147(4) 0.24071(17) 0.0435(8) Uani 1 1 d .
H8A H 0.3595 0.7073 0.2405 0.052 Uiso 1 1 calc R
N1 N 0.2547(3) 0.6473(4) 0.09418(19) 0.0587(9) Uani 1 1 d .
N2 N 0.5495(3) 0.3899(3) 0.06219(17) 0.0525(8) Uani 1 1 d .
C16 C 0.7288(3) 0.6581(4) 0.03762(18) 0.0452(8) Uani 1 1 d .
H16A H 0.6699 0.6302 0.0045 0.054 Uiso 1 1 calc R
C3 C 0.5561(4) 1.0004(4) 0.11955(19) 0.0466(9) Uani 1 1 d .
H3A H 0.5771 1.0670 0.1557 0.056 Uiso 1 1 calc R
H3B H 0.6272 0.9907 0.0924 0.056 Uiso 1 1 calc R
C12 C 0.7805(3) 0.7677(4) 0.14141(18) 0.0449(8) Uani 1 1 d .
H12A H 0.7580 0.8147 0.1803 0.054 Uiso 1 1 calc R
C23 C 0.3524(4) 0.6314(4) 0.1093(3) 0.0636(12) Uani 1 1 d .
C26 C 0.6284(3) 0.5494(4) 0.21689(19) 0.0445(8) Uani 1 1 d .
C13 C 0.9001(4) 0.7451(5) 0.1312(2) 0.0576(11) Uani 1 1 d .
H13A H 0.9595 0.7765 0.1632 0.069 Uiso 1 1 calc R
C17 C 0.4979(3) 0.7011(4) 0.31213(17) 0.0410(8) Uani 1 1 d .
C7 C 0.4977(4) 0.5847(4) 0.2008(2) 0.0553(10) Uani 1 1 d .
N3 N 0.3690(3) 0.3676(4) 0.2316(2) 0.0619(10) Uani 1 1 d .
C18 C 0.6090(3) 0.7559(4) 0.3315(2) 0.0484(9) Uani 1 1 d .
H18A H 0.6537 0.8052 0.3003 0.058 Uiso 1 1 calc R
C2 C 0.4533(4) 1.0596(4) 0.0763(2) 0.0540(10) Uani 1 1 d .
H2A H 0.4705 1.1410 0.0522 0.065 Uiso 1 1 calc R
C19 C 0.6556(4) 0.7395(5) 0.3961(2) 0.0580(11) Uani 1 1 d .
H19A H 0.7320 0.7774 0.4089 0.070 Uiso 1 1 calc R
C6 C 0.4882(4) 0.6107(4) 0.1256(2) 0.0564(10) Uani 1 1 d .
C22 C 0.4327(4) 0.6311(5) 0.3588(2) 0.0535(10) Uani 1 1 d .
H22A H 0.3553 0.5948 0.3467 0.064 Uiso 1 1 calc R
C10 C 0.4435(4) 0.9755(4) 0.2474(2) 0.0543(10) Uani 1 1 d .
H10A H 0.4656 1.0600 0.2240 0.081 Uiso 1 1 calc R
H10B H 0.4852 0.9736 0.2915 0.081 Uiso 1 1 calc R
H10C H 0.3564 0.9741 0.2523 0.081 Uiso 1 1 calc R
C25 C 0.4207(4) 0.4630(4) 0.2179(2) 0.0532(10) Uani 1 1 d .
C1 C 0.3432(4) 1.0115(5) 0.0682(2) 0.0614(11) Uani 1 1 d .
H1A H 0.3206 0.9303 0.0911 0.074 Uiso 1 1 calc R
H1B H 0.2860 1.0580 0.0395 0.074 Uiso 1 1 calc R
C15 C 0.8492(4) 0.6344(5) 0.0278(2) 0.0604(11) Uani 1 1 d .
H15A H 0.8727 0.5887 -0.0112 0.072 Uiso 1 1 calc R
C21 C 0.4811(5) 0.6147(6) 0.4230(2) 0.0716(14) Uani 1 1 d .
H21A H 0.4373 0.5654 0.4546 0.086 Uiso 1 1 calc R
C20 C 0.5919(4) 0.6689(6) 0.4415(2) 0.0684(13) Uani 1 1 d .
H20A H 0.6242 0.6575 0.4858 0.082 Uiso 1 1 calc R
C14 C 0.9350(4) 0.6780(5) 0.0755(3) 0.0658(12) Uani 1 1 d .
H14A H 1.0179 0.6613 0.0696 0.079 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 C5 C11 114.5(3)
C4 C5 C6 110.2(3)
C11 C5 C6 116.8(3)
C4 C5 H5A 104.7
C11 C5 H5A 104.7
C6 C5 H5A 104.7
C12 C11 C16 118.3(3)
C12 C11 C5 122.0(3)
C16 C11 C5 119.7(3)
C9 C4 C5 125.3(3)
C9 C4 C3 121.8(3)
C5 C4 C3 112.8(3)
N2 C24 C6 174.7(4)
C4 C9 C10 122.6(3)
C4 C9 C8 124.0(3)
C10 C9 C8 113.4(3)
C9 C8 C17 114.0(3)
C9 C8 C7 112.2(3)
C17 C8 C7 107.1(3)
C9 C8 H8A 107.8
C17 C8 H8A 107.8
C7 C8 H8A 107.8
C15 C16 C11 121.1(4)
C15 C16 H16A 119.4
C11 C16 H16A 119.4
C2 C3 C4 114.4(3)
C2 C3 H3A 108.7
C4 C3 H3A 108.7
C2 C3 H3B 108.7
C4 C3 H3B 108.7
H3A C3 H3B 107.6
C13 C12 C11 120.3(4)
C13 C12 H12A 119.8
C11 C12 H12A 119.8
N1 C23 C6 176.5(6)
N4 C26 C7 170.9(4)
C14 C13 C12 121.1(4)
C14 C13 H13A 119.5
C12 C13 H13A 119.5
C18 C17 C22 119.0(3)
C18 C17 C8 120.4(3)
C22 C17 C8 120.6(3)
C25 C7 C26 109.1(3)
C25 C7 C6 110.0(3)
C26 C7 C6 105.3(4)
C25 C7 C8 106.7(3)
C26 C7 C8 114.6(3)
C6 C7 C8 111.1(3)
C19 C18 C17 120.5(4)
C19 C18 H18A 119.7
C17 C18 H18A 119.7
C1 C2 C3 127.6(4)
C1 C2 H2A 116.2
C3 C2 H2A 116.2
C20 C19 C18 120.3(4)
C20 C19 H19A 119.9
C18 C19 H19A 119.9
C24 C6 C7 108.6(3)
C24 C6 C23 108.5(4)
C7 C6 C23 104.3(4)
C24 C6 C5 112.7(3)
C7 C6 C5 112.2(3)
C23 C6 C5 110.2(3)
C21 C22 C17 119.6(4)
C21 C22 H22A 120.2
C17 C22 H22A 120.2
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N3 C25 C7 175.9(5)
C2 C1 H1A 120.0
C2 C1 H1B 120.0
H1A C1 H1B 120.0
C16 C15 C14 119.3(4)
C16 C15 H15A 120.3
C14 C15 H15A 120.3
C20 C21 C22 120.8(4)
C20 C21 H21A 119.6
C22 C21 H21A 119.6
C19 C20 C21 119.8(4)
C19 C20 H20A 120.1
C21 C20 H20A 120.1
C13 C14 C15 119.8(4)
C13 C14 H14A 120.1
C15 C14 H14A 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N4 C26 1.126(4)
C5 C4 1.514(5)
C5 C11 1.525(5)
C5 C6 1.547(5)
C5 H5A 1.0000
C11 C12 1.386(5)
C11 C16 1.394(5)
C4 C9 1.324(5)
C4 C3 1.514(4)
C24 N2 1.124(5)
C24 C6 1.474(5)
C9 C10 1.503(5)
C9 C8 1.517(5)
C8 C17 1.517(5)
C8 C7 1.600(6)
C8 H8A 1.0000
N1 C23 1.124(5)
C16 C15 1.383(6)
C16 H16A 0.9500
C3 C2 1.514(6)
C3 H3A 0.9900
C3 H3B 0.9900
C12 C13 1.376(6)
C12 H12A 0.9500
C23 C6 1.544(6)
C26 C7 1.513(6)
C13 C14 1.369(7)
C13 H13A 0.9500
C17 C18 1.384(5)
C17 C22 1.392(5)
C7 C25 1.506(5)
C7 C6 1.535(6)
N3 C25 1.129(5)
C18 C19 1.383(6)
C18 H18A 0.9500
C2 C1 1.313(6)
C2 H2A 0.9500
C19 C20 1.369(6)
C19 H19A 0.9500
C22 C21 1.384(6)
C22 H22A 0.9500
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C1 H1A 0.9500
C1 H1B 0.9500
C15 C14 1.385(6)
C15 H15A 0.9500
C21 C20 1.373(7)
C21 H21A 0.9500
C20 H20A 0.9500
C14 H14A 0.9500
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 C5 C11 C12 25.8(4)
C6 C5 C11 C12 -105.1(4)
C4 C5 C11 C16 -153.8(3)
C6 C5 C11 C16 75.3(4)
C11 C5 C4 C9 -116.6(4)
C6 C5 C4 C9 17.4(5)
C11 C5 C4 C3 67.4(4)
C6 C5 C4 C3 -158.6(3)
C5 C4 C9 C10 -174.8(3)
C3 C4 C9 C10 0.8(6)
C5 C4 C9 C8 3.3(6)
C3 C4 C9 C8 178.9(3)
C4 C9 C8 C17 128.2(4)
C10 C9 C8 C17 -53.5(4)
C4 C9 C8 C7 6.2(5)
C10 C9 C8 C7 -175.5(3)
C12 C11 C16 C15 3.0(6)
C5 C11 C16 C15 -177.4(4)
C9 C4 C3 C2 -88.3(4)
C5 C4 C3 C2 87.8(4)
C16 C11 C12 C13 -2.3(5)
C5 C11 C12 C13 178.0(3)
C11 C12 C13 C14 0.2(7)
C9 C8 C17 C18 -36.6(5)
C7 C8 C17 C18 88.1(4)
C9 C8 C17 C22 144.6(4)
C7 C8 C17 C22 -90.7(4)
N4 C26 C7 C25 -40(3)
N4 C26 C7 C6 -158(2)
N4 C26 C7 C8 80(3)
C9 C8 C7 C25 -156.1(3)
C17 C8 C7 C25 78.1(4)
C9 C8 C7 C26 83.1(4)
C17 C8 C7 C26 -42.8(4)
C9 C8 C7 C6 -36.1(4)
C17 C8 C7 C6 -162.0(3)
C22 C17 C18 C19 1.0(6)
C8 C17 C18 C19 -177.8(4)
C4 C3 C2 C1 7.3(6)
C17 C18 C19 C20 -0.1(7)
N2 C24 C6 C7 136(4)
N2 C24 C6 C23 23(5)
N2 C24 C6 C5 -99(5)
C25 C7 C6 C24 -58.7(5)
C26 C7 C6 C24 58.8(4)
C8 C7 C6 C24 -176.6(3)
C25 C7 C6 C23 56.8(4)
C26 C7 C6 C23 174.3(3)
C8 C7 C6 C23 -61.1(4)
C25 C7 C6 C5 176.1(3)
C26 C7 C6 C5 -66.4(4)
C8 C7 C6 C5 58.2(5)
N1 C23 C6 C24 -63(7)
N1 C23 C6 C7 -178(100)
N1 C23 C6 C5 61(7)
C4 C5 C6 C24 -170.7(3)
C11 C5 C6 C24 -37.9(5)
C4 C5 C6 C7 -47.8(4)
C11 C5 C6 C7 85.0(4)
C4 C5 C6 C23 68.0(4)
C11 C5 C6 C23 -159.2(3)
C18 C17 C22 C21 -1.6(7)
C8 C17 C22 C21 177.2(4)
C26 C7 C25 N3 -5(7)
C6 C7 C25 N3 110(7)
C8 C7 C25 N3 -129(7)
C11 C16 C15 C14 -1.5(7)
C17 C22 C21 C20 1.2(8)
C18 C19 C20 C21 -0.3(8)
C22 C21 C20 C19 -0.3(9)
C12 C13 C14 C15 1.4(8)
C16 C15 C14 C13 -0.7(8)
