#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/80/4108011.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_4108011
loop_
_publ_author_name
'Brant C. Boren'
'Sridhar Narayan'
'Lars K. Rasmussen'
'Li Zhang'
'Haitao Zhao'
'Zhenyang Lin'
'Guochen Jia'
'Valery V. Fokin'
_publ_section_title
;
 Ruthenium-Catalyzed Azide-Alkyne Cycloaddition: Scope and Mechanism
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8923
_journal_page_last               8930
_journal_paper_doi               10.1021/ja0749993
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C18 H16 N4 O2'
_chemical_formula_weight         320.35
_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                 98.716(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0964(19)
_cell_length_b                   5.8325(10)
_cell_length_c                   24.085(4)
_cell_measurement_reflns_used    7673
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.16
_cell_volume                     1540.8(5)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            13383
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_correction_T_min  0.9725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       rod
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.057
_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     217
_refine_ls_number_reflns         3569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.4400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                3045
_reflns_number_total             3569
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0749993-file004.cif
_cod_data_source_block           sharp05
_cod_database_code               4108011
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
O1 O 0.64262(8) 0.45914(16) 0.99688(4) 0.0224(2) Uani 1 1 d .
O2 O 0.68845(9) 0.73461(16) 0.93823(4) 0.0254(2) Uani 1 1 d .
N1 N 0.54780(10) 0.5305(2) 0.75822(5) 0.0229(3) Uani 1 1 d .
N2 N 0.62733(10) 0.3615(2) 0.76296(5) 0.0235(3) Uani 1 1 d .
N3 N 0.64956(10) 0.30069(19) 0.81729(4) 0.0196(2) Uani 1 1 d .
N4 N 0.59116(9) 0.39881(18) 0.90569(4) 0.0177(2) Uani 1 1 d .
C1 C 0.41653(12) 0.9474(2) 0.78121(6) 0.0225(3) Uani 1 1 d .
H1B H 0.4674 0.9606 0.7530 0.027 Uiso 1 1 calc R
C2 C 0.33110(12) 1.1156(2) 0.78636(6) 0.0258(3) Uani 1 1 d .
H2B H 0.3234 1.2433 0.7616 0.031 Uiso 1 1 calc R
C3 C 0.25644(12) 1.0989(2) 0.82758(6) 0.0263(3) Uani 1 1 d .
H3A H 0.1976 1.2143 0.8310 0.032 Uiso 1 1 calc R
C4 C 0.26850(12) 0.9121(2) 0.86382(6) 0.0248(3) Uani 1 1 d .
H4A H 0.2185 0.9011 0.8924 0.030 Uiso 1 1 calc R
C5 C 0.35308(11) 0.7415(2) 0.85846(5) 0.0215(3) Uani 1 1 d .
H5A H 0.3597 0.6129 0.8829 0.026 Uiso 1 1 calc R
C6 C 0.42859(11) 0.7580(2) 0.81723(5) 0.0196(3) Uani 1 1 d .
C7 C 0.51728(11) 0.5783(2) 0.80973(5) 0.0196(3) Uani 1 1 d .
C8 C 0.58328(11) 0.4323(2) 0.84774(5) 0.0174(3) Uani 1 1 d .
C9 C 0.53271(12) 0.2097(2) 0.93110(5) 0.0204(3) Uani 1 1 d .
H9A H 0.5456 0.0612 0.9130 0.025 Uiso 1 1 calc R
H9B H 0.4443 0.2363 0.9301 0.025 Uiso 1 1 calc R
C10 C 0.60203(13) 0.2227(2) 0.99064(5) 0.0239(3) Uani 1 1 d .
H10A H 0.5481 0.1841 1.0185 0.029 Uiso 1 1 calc R
H10B H 0.6724 0.1164 0.9955 0.029 Uiso 1 1 calc R
C11 C 0.64586(11) 0.5496(2) 0.94520(5) 0.0184(3) Uani 1 1 d .
C12 C 0.74379(12) 0.1328(2) 0.83742(6) 0.0224(3) Uani 1 1 d .
H12A H 0.7657 0.0455 0.8051 0.027 Uiso 1 1 calc R
H12B H 0.7118 0.0232 0.8630 0.027 Uiso 1 1 calc R
C13 C 0.85621(12) 0.2492(2) 0.86819(5) 0.0220(3) Uani 1 1 d .
C14 C 0.92175(14) 0.1487(3) 0.91566(6) 0.0333(3) Uani 1 1 d .
H14A H 0.8945 0.0087 0.9297 0.040 Uiso 1 1 calc R
C15 C 1.02701(16) 0.2526(4) 0.94267(7) 0.0438(4) Uani 1 1 d .
H15A H 1.0719 0.1826 0.9750 0.053 Uiso 1 1 calc R
C16 C 1.06708(14) 0.4567(3) 0.92304(7) 0.0408(4) Uani 1 1 d .
H16A H 1.1391 0.5273 0.9418 0.049 Uiso 1 1 calc R
C17 C 1.00157(13) 0.5581(3) 0.87571(7) 0.0335(4) Uani 1 1 d .
H17A H 1.0287 0.6987 0.8620 0.040 Uiso 1 1 calc R
C18 C 0.89685(12) 0.4545(2) 0.84860(6) 0.0262(3) Uani 1 1 d .
H18A H 0.8523 0.5246 0.8162 0.031 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
C11 O1 C10 108.98(10)
N2 N1 C7 109.27(11)
N1 N2 N3 107.71(10)
N2 N3 C8 110.11(11)
N2 N3 C12 121.15(11)
C8 N3 C12 128.38(11)
C11 N4 C8 123.94(11)
C11 N4 C9 111.87(10)
C8 N4 C9 123.98(10)
C2 C1 C6 120.49(13)
C1 C2 C3 120.36(13)
C4 C3 C2 119.51(13)
C5 C4 C3 120.40(13)
C4 C5 C6 120.28(12)
C5 C6 C1 118.96(12)
C5 C6 C7 121.63(12)
C1 C6 C7 119.39(12)
N1 C7 C8 107.32(11)
N1 C7 C6 121.46(11)
C8 C7 C6 131.22(12)
N3 C8 C7 105.58(11)
N3 C8 N4 120.31(11)
C7 C8 N4 134.11(12)
N4 C9 C10 99.43(10)
O1 C10 C9 104.45(10)
O2 C11 O1 122.93(11)
O2 C11 N4 128.55(12)
O1 C11 N4 108.50(11)
N3 C12 C13 110.96(11)
C18 C13 C14 119.19(13)
C18 C13 C12 120.50(12)
C14 C13 C12 120.29(13)
C15 C14 C13 120.04(16)
C16 C15 C14 120.56(15)
C15 C16 C17 119.59(15)
C18 C17 C16 119.95(15)
C17 C18 C13 120.67(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C11 1.3573(15)
O1 C10 1.4512(17)
O2 C11 1.2002(16)
N1 N2 1.3165(17)
N1 C7 1.3635(17)
N2 N3 1.3420(15)
N3 C8 1.3533(16)
N3 C12 1.4606(17)
N4 C11 1.3682(16)
N4 C8 1.3989(16)
N4 C9 1.4601(16)
C1 C2 1.383(2)
C1 C6 1.3986(18)
C2 C3 1.390(2)
C3 C4 1.390(2)
C4 C5 1.3871(19)
C5 C6 1.3964(19)
C6 C7 1.4672(19)
C7 C8 1.3773(18)
C9 C10 1.5230(18)
C12 C13 1.5118(19)
C13 C18 1.387(2)
C13 C14 1.388(2)
C14 C15 1.387(2)
C15 C16 1.379(3)
C16 C17 1.388(2)
C17 C18 1.383(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660321
