#------------------------------------------------------------------------------
#$Date: 2017-09-06 05:26:11 +0300 (Wed, 06 Sep 2017) $
#$Revision: 200195 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/41/7044117.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_7044117
loop_
_publ_author_name
'Martínez, Antonio'
'Moreno-Blázquez, Sonia'
'Rodriguez-Dieguez, Antonio'
'Ramos, Alberto'
'Fernandez-Galan, Rafael'
'Antiñolo, Antonio'
'CARRILLO-HERMOSILLA, FERNANDO'
_publ_section_title
;
 Simple ZnEt2 as catalyst in carbodiimide hydroalkynylation: structural
 and mechanistic studies
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT02700A
_journal_year                    2017
_chemical_formula_sum            'C46 H50 N4 Zn'
_chemical_formula_weight         724.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-06-15 deposited with the CCDC.
2017-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.144(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.358(2)
_cell_length_b                   19.359(3)
_cell_length_c                   20.131(3)
_cell_measurement_reflns_used    12420
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.33
_cell_volume                     3973.6(11)
_computing_cell_refinement       'Bruker Apex II'
_computing_data_collection       'Bruker ApexII'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            50683
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         27.913
_diffrn_reflns_theta_min         2.257
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.688
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             1536
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0348
_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)+(0.0222P)²+5.1879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0735
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3919
_reflns_number_total             4773
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7dt02700a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' 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        3973.6(12)
_cod_database_code               7044117
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Zn1 Zn 0.500000 0.23937(2) 0.750000 0.01143(7) Uani 1 2 d S T P
C7 C 0.03657(17) -0.00893(9) 0.35392(9) 0.0232(4) Uani 1 1 d . . .
H7 H -0.007666 -0.032942 0.316760 0.028 Uiso 1 1 calc R U .
C20 C 0.07296(17) 0.46612(9) 0.86139(10) 0.0246(4) Uani 1 1 d . . .
H20 H 0.078632 0.513086 0.871169 0.030 Uiso 1 1 calc R U .
C15 C 0.56888(18) 0.27410(9) 0.50314(9) 0.0232(4) Uani 1 1 d . . .
H15A H 0.501838 0.308890 0.498340 0.035 Uiso 1 1 d R U .
H15B H 0.598319 0.268050 0.460890 0.035 Uiso 1 1 d R U .
H15C H 0.641311 0.288175 0.537004 0.035 Uiso 1 1 d R U .
N1 N 0.38219(12) 0.17426(6) 0.67905(6) 0.0118(3) Uani 1 1 d . . .
N2 N 0.47188(13) 0.21733(7) 0.58927(7) 0.0160(3) Uani 1 1 d . . .
H2 H 0.532205 0.241396 0.620887 0.019 Uiso 1 1 d R U .
C18 C 0.17411(15) 0.36110(8) 0.83105(8) 0.0134(3) Uani 1 1 d . . .
C9 C 0.12627(16) 0.09681(9) 0.40387(8) 0.0194(4) Uani 1 1 d . . .
H9 H 0.141739 0.143883 0.400394 0.023 Uiso 1 1 calc R U .
C23 C 0.05676(16) 0.32649(9) 0.83357(8) 0.0179(3) Uani 1 1 d . . .
H23 H 0.050835 0.279331 0.824731 0.021 Uiso 1 1 calc R U .
C2 C 0.30377(15) 0.13393(8) 0.56496(8) 0.0150(3) Uani 1 1 d . . .
C19 C 0.18078(16) 0.43182(9) 0.84557(9) 0.0200(4) Uani 1 1 d . . .
H19 H 0.258100 0.455908 0.844585 0.024 Uiso 1 1 calc R U .
C5 C 0.14572(17) -0.00815(9) 0.46950(9) 0.0221(4) Uani 1 1 d . . .
H5 H 0.174427 -0.031424 0.509806 0.027 Uiso 1 1 calc R U .
C17 C 0.28250(15) 0.32459(8) 0.81079(8) 0.0143(3) Uani 1 1 d . . .
C4 C 0.16997(14) 0.06240(8) 0.46457(8) 0.0142(3) Uani 1 1 d . . .
C14 C 0.61240(18) 0.14748(10) 0.52833(9) 0.0252(4) Uani 1 1 d . . .
H14A H 0.688667 0.158572 0.561095 0.038 Uiso 1 1 d R U .
H14B H 0.637321 0.140843 0.485047 0.038 Uiso 1 1 d R U .
H14C H 0.573303 0.105878 0.541554 0.038 Uiso 1 1 d R U .
C3 C 0.24155(15) 0.10035(8) 0.52064(8) 0.0157(3) Uani 1 1 d . . .
C12 C 0.31370(17) 0.10576(9) 0.77025(9) 0.0216(4) Uani 1 1 d . . .
H12A H 0.392877 0.079302 0.773149 0.032 Uiso 1 1 d R U .
H12B H 0.245102 0.076817 0.781124 0.032 Uiso 1 1 d R U .
H12C H 0.328268 0.143608 0.801486 0.032 Uiso 1 1 d R U .
C6 C 0.07861(18) -0.04338(9) 0.41400(9) 0.0258(4) Uani 1 1 d . . .
H6 H 0.061816 -0.090344 0.417209 0.031 Uiso 1 1 calc R U .
C10 C 0.27381(15) 0.13353(8) 0.69907(8) 0.0139(3) Uani 1 1 d . . .
H10 H 0.255320 0.094196 0.668213 0.017 Uiso 1 1 calc R U .
C21 C -0.04317(16) 0.43132(9) 0.86281(9) 0.0214(4) Uani 1 1 d . . .
H21 H -0.115541 0.454825 0.872977 0.026 Uiso 1 1 calc R U .
C16 C 0.36879(15) 0.29239(8) 0.79128(8) 0.0146(3) Uani 1 1 d . . .
C22 C -0.05085(16) 0.36132(9) 0.84901(9) 0.0204(4) Uani 1 1 d . . .
H22 H -0.128509 0.337582 0.850111 0.024 Uiso 1 1 calc R U .
C11 C 0.15064(15) 0.17812(9) 0.69198(9) 0.0189(3) Uani 1 1 d . . .
H11A H 0.168721 0.218462 0.719797 0.028 Uiso 1 1 d R U .
H11B H 0.081135 0.152187 0.706001 0.028 Uiso 1 1 d R U .
H11C H 0.124674 0.191837 0.645729 0.028 Uiso 1 1 d R U .
C13 C 0.51393(16) 0.20625(9) 0.52398(8) 0.0174(3) Uani 1 1 d . . .
H13 H 0.436782 0.194074 0.490416 0.021 Uiso 1 1 calc R U .
C8 C 0.05989(17) 0.06088(10) 0.34881(9) 0.0244(4) Uani 1 1 d . . .
H8 H 0.030982 0.083816 0.308328 0.029 Uiso 1 1 calc R U .
C1 C 0.38824(14) 0.17538(8) 0.61480(8) 0.0128(3) 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'
Zn Zn 0.2839 1.4301 '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
C16 Zn1 C16 118.14(9) . 2_656
C16 Zn1 N1 103.44(6) . .
C16 Zn1 N1 112.21(6) 2_656 .
C16 Zn1 N1 112.21(6) . 2_656
C16 Zn1 N1 103.44(6) 2_656 2_656
N1 Zn1 N1 107.13(7) . 2_656
C8 C7 C6 120.36(16) . .
C21 C20 C19 120.73(16) . .
C1 N1 C10 116.62(13) . .
C1 N1 Zn1 122.31(10) . .
C10 N1 Zn1 120.36(9) . .
C1 N2 C13 124.17(13) . .
C23 C18 C19 118.24(14) . .
C23 C18 C17 120.00(14) . .
C19 C18 C17 121.69(14) . .
C8 C9 C4 120.00(16) . .
C22 C23 C18 120.99(15) . .
C3 C2 C1 174.76(17) . .
C20 C19 C18 120.36(15) . .
C6 C5 C4 119.68(16) . .
C16 C17 C18 176.68(17) . .
C5 C4 C9 119.66(15) . .
C5 C4 C3 121.24(15) . .
C9 C4 C3 119.10(15) . .
C2 C3 C4 176.64(18) . .
C7 C6 C5 120.23(17) . .
N1 C10 C12 110.56(12) . .
N1 C10 C11 109.50(13) . .
C12 C10 C11 111.88(14) . .
C22 C21 C20 119.51(16) . .
C17 C16 Zn1 174.30(14) . .
C21 C22 C23 120.16(16) . .
N2 C13 C15 107.74(13) . .
N2 C13 C14 111.03(14) . .
C15 C13 C14 112.50(14) . .
C7 C8 C9 120.07(16) . .
N1 C1 N2 122.11(14) . .
N1 C1 C2 123.18(14) . .
N2 C1 C2 114.68(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 C16 1.9973(16) .
Zn1 C16 1.9973(16) 2_656
Zn1 N1 2.1222(13) .
Zn1 N1 2.1222(13) 2_656
C7 C8 1.380(3) .
C7 C6 1.383(3) .
C20 C21 1.383(2) .
C20 C19 1.384(2) .
C15 C13 1.520(2) .
N1 C1 1.306(2) .
N1 C10 1.4845(19) .
N2 C1 1.353(2) .
N2 C13 1.472(2) .
C18 C23 1.397(2) .
C18 C19 1.399(2) .
C18 C17 1.445(2) .
C9 C8 1.384(2) .
C9 C4 1.395(2) .
C23 C22 1.384(2) .
C2 C3 1.196(2) .
C2 C1 1.452(2) .
C5 C6 1.387(2) .
C5 C4 1.395(2) .
C17 C16 1.211(2) .
C4 C3 1.438(2) .
C14 C13 1.520(2) .
C12 C10 1.518(2) .
C10 C11 1.526(2) .
C21 C22 1.383(2) .
