#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:48:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178406 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/27/4022714.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_4022714
loop_
_publ_author_name
'Laura D. Shirtcliff'
'Michael M. Haley'
'Rainer Herges'
_publ_section_title
;
 CuCl-Induced Formation and Migration of Isoindazolyl Carbenoids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2411
_journal_page_last               2418
_journal_paper_doi               10.1021/jo0622274
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C26 H30 Cl N3'
_chemical_formula_weight         419.98
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 111.333(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.063(5)
_cell_length_b                   10.356(5)
_cell_length_c                   12.085(6)
_cell_measurement_reflns_used    380
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      16.16
_cell_measurement_theta_min      3.48
_cell_volume                     1173.1(10)
_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      153(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1495
_diffrn_reflns_av_sigmaI/netI    0.1458
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8291
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.1687
_refine_ls_R_factor_gt           0.0715
_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)+(0.0558P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1560
_reflns_number_gt                1073
_reflns_number_total             2184
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0622274si20061026_044524.cif
_cod_data_source_block           lds2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4022714
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-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
Cl Cl -0.53423(17) 0.2500 0.16375(15) 0.0517(6) Uani 1 2 d S
N1 N 0.0824(5) 0.2500 0.2795(4) 0.0311(12) Uani 1 2 d S
N2 N 0.1198(5) 0.2500 0.3993(4) 0.0253(12) Uani 1 2 d S
N3 N 0.2620(5) 0.2500 0.4769(4) 0.0320(12) Uani 1 2 d S
C1 C -0.3513(6) 0.2500 0.1972(5) 0.0299(15) Uani 1 2 d S
C2 C -0.3018(7) 0.2500 0.1004(5) 0.0344(16) Uani 1 2 d S
H2 H -0.3690 0.2500 0.0212 0.041 Uiso 1 2 calc SR
C3 C -0.1592(7) 0.2500 0.1199(5) 0.0337(16) Uani 1 2 d S
H3 H -0.1262 0.2500 0.0556 0.040 Uiso 1 2 calc SR
C4 C -0.0625(6) 0.2500 0.2390(5) 0.0259(14) Uani 1 2 d S
C5 C -0.1137(6) 0.2500 0.3343(5) 0.0255(14) Uani 1 2 d S
C6 C -0.2599(6) 0.2500 0.3115(5) 0.0287(15) Uani 1 2 d S
H6 H -0.2945 0.2500 0.3749 0.034 Uiso 1 2 calc SR
C7 C 0.0073(6) 0.2500 0.4367(5) 0.0252(14) Uani 1 2 d S
C8 C 0.0229(6) 0.2500 0.5581(5) 0.0277(14) Uani 1 2 d S
C9 C 0.0263(6) 0.2500 0.6585(5) 0.0277(14) Uani 1 2 d S
C10 C 0.0335(6) 0.2500 0.7811(5) 0.0227(13) Uani 1 2 d S
C11 C 0.1590(4) 0.3222(4) 0.8717(3) 0.0245(10) Uani 1 1 d .
C12 C 0.2613(4) 0.3967(4) 0.8280(4) 0.0336(11) Uani 1 1 d .
H12A H 0.3544 0.4040 0.8926 0.050 Uiso 1 1 calc R
H12B H 0.2230 0.4832 0.8024 0.050 Uiso 1 1 calc R
H12C H 0.2723 0.3506 0.7610 0.050 Uiso 1 1 calc R
C13 C 0.1345(4) 0.3966(4) 0.9722(3) 0.0318(11) Uani 1 1 d .
H13A H 0.0634 0.3512 0.9956 0.048 Uiso 1 1 calc R
H13B H 0.1000 0.4837 0.9447 0.048 Uiso 1 1 calc R
H13C H 0.2244 0.4025 1.0405 0.048 Uiso 1 1 calc R
C14 C -0.1143(6) 0.2500 0.7864(5) 0.0249(14) Uani 1 2 d S
C15 C -0.1861(4) 0.3660(4) 0.7832(3) 0.0312(11) Uani 1 1 d .
H15 H -0.1389 0.4458 0.7848 0.037 Uiso 1 1 calc R
C16 C -0.3260(4) 0.3651(4) 0.7777(4) 0.0376(12) Uani 1 1 d .
H16 H -0.3737 0.4445 0.7769 0.045 Uiso 1 1 calc R
C17 C -0.3968(6) 0.2500 0.7733(5) 0.0379(17) Uani 1 2 d S
H17 H -0.4936 0.2500 0.7674 0.045 Uiso 1 2 calc SR
C18 C 0.3349(5) 0.3692(4) 0.4611(4) 0.0385(12) Uani 1 1 d .
H18A H 0.3264 0.3764 0.3771 0.046 Uiso 1 1 calc R
H18B H 0.4376 0.3639 0.5108 0.046 Uiso 1 1 calc R
C19 C 0.2710(5) 0.4877(4) 0.4954(4) 0.0515(14) Uani 1 1 d .
H19A H 0.1685 0.4911 0.4484 0.077 Uiso 1 1 calc R
H19B H 0.3173 0.5653 0.4799 0.077 Uiso 1 1 calc R
H19C H 0.2856 0.4836 0.5800 0.077 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N2 N1 C4 103.3(4) . .
N1 N2 C7 114.3(4) . .
N1 N2 N3 122.4(4) . .
C7 N2 N3 123.3(4) . .
N2 N3 C18 110.4(3) . 4_565
N2 N3 C18 110.4(3) . .
C18 N3 C18 112.6(4) 4_565 .
C6 C1 C2 121.7(5) . .
C6 C1 Cl 120.5(4) . .
C2 C1 Cl 117.7(5) . .
C3 C2 C1 121.0(6) . .
C2 C3 C4 117.8(5) . .
N1 C4 C3 128.2(5) . .
N1 C4 C5 111.4(5) . .
C3 C4 C5 120.4(5) . .
C7 C5 C6 134.2(5) . .
C7 C5 C4 105.3(5) . .
C6 C5 C4 120.5(5) . .
C1 C6 C5 118.5(5) . .
N2 C7 C5 105.6(5) . .
N2 C7 C8 123.4(5) . .
C5 C7 C8 131.0(5) . .
C9 C8 C7 175.6(6) . .
C8 C9 C10 178.9(6) . .
C9 C10 C14 110.9(5) . .
C9 C10 C11 116.7(4) . .
C14 C10 C11 122.5(4) . .
C9 C10 C11 116.7(4) . 4_565
C14 C10 C11 122.5(4) . 4_565
C11 C10 C11 58.4(3) . 4_565
C11 C11 C12 120.3(2) 4_565 .
C11 C11 C13 120.2(2) 4_565 .
C12 C11 C13 110.1(3) . .
C11 C11 C10 60.79(17) 4_565 .
C12 C11 C10 118.9(3) . .
C13 C11 C10 118.9(3) . .
C15 C14 C15 118.8(5) . 4_565
C15 C14 C10 120.4(2) . .
C15 C14 C10 120.4(2) 4_565 .
C16 C15 C14 120.2(4) . .
C17 C16 C15 120.6(4) . .
C16 C17 C16 119.5(5) . 4_565
N3 C18 C19 111.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl C1 1.735(6) .
N1 N2 1.357(6) .
N1 C4 1.358(7) .
N2 C7 1.363(6) .
N2 N3 1.397(6) .
N3 C18 1.483(4) 4_565
N3 C18 1.483(4) .
C1 C6 1.353(7) .
C1 C2 1.429(7) .
C2 C3 1.367(8) .
C3 C4 1.414(8) .
C4 C5 1.423(7) .
C5 C7 1.385(7) .
C5 C6 1.395(7) .
C7 C8 1.417(7) .
C8 C9 1.202(7) .
C9 C10 1.456(8) .
C10 C14 1.512(7) .
C10 C11 1.532(6) .
C10 C11 1.532(6) 4_565
C11 C11 1.496(7) 4_565
C11 C12 1.526(5) .
C11 C13 1.532(5) .
C14 C15 1.395(4) .
C14 C15 1.395(4) 4_565
C15 C16 1.385(5) .
C16 C17 1.380(5) .
C17 C16 1.380(5) 4_565
C18 C19 1.513(5) .
