#------------------------------------------------------------------------------
#$Date: 2025-08-21 14:03:24 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301848 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/23/7022362.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_7022362
loop_
_publ_author_name
'Kreye, Markus'
'Glöckner, Andreas'
'Daniliuc, Constantin G.'
'Freytag, Matthias'
'Jones, Peter G.'
'Tamm, Matthias'
'Walter, Marc D.'
_publ_section_title
;
 Sterically encumbered pyrrolyl ligands and their incorporation into the
 cycloheptatrienyl zirconium coordination sphere.
;
_journal_issue                   6
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2192
_journal_page_last               2200
_journal_paper_doi               10.1039/c2dt32433d
_journal_volume                  42
_journal_year                    2013
_chemical_formula_sum            'C14 H25 N O2'
_chemical_formula_weight         239.35
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.310(7)
_cell_angle_beta                 63.418(8)
_cell_angle_gamma                82.113(7)
_cell_formula_units_Z            2
_cell_length_a                   8.7383(8)
_cell_length_b                   9.5314(8)
_cell_length_c                   9.7570(8)
_cell_measurement_reflns_used    17074
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9515
_cell_measurement_theta_min      4.7040
_cell_volume                     716.17(12)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3543
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0103
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            30721
_diffrn_reflns_theta_full        75.00
_diffrn_reflns_theta_max         76.14
_diffrn_reflns_theta_min         4.71
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0522P)²+0.2349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1052
_reflns_number_gt                2774
_reflns_number_total             2965
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt32433d.txt
_cod_data_source_block           mk64
_cod_original_cell_volume        716.17(11)
_cod_database_code               7022362
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
N N 0.12432(11) 0.29970(9) 0.50796(10) 0.0232(2) Uani 1 1 d .
O1 O 0.06046(10) 0.48343(8) 0.67063(9) 0.02656(19) Uani 1 1 d .
O2 O 0.15618(10) 0.57599(8) 0.53214(9) 0.0296(2) Uani 1 1 d .
H02 H 0.052(3) 0.625(2) 0.517(2) 0.069(6) Uiso 1 1 d .
C1 C 0.13385(13) 0.34250(11) 0.64259(12) 0.0230(2) Uani 1 1 d .
C2 C 0.32393(14) 0.32580(11) 0.60319(12) 0.0243(2) Uani 1 1 d .
C3 C 0.40809(14) 0.26819(11) 0.46904(12) 0.0247(2) Uani 1 1 d .
C4 C 0.27608(14) 0.25457(11) 0.41464(12) 0.0234(2) Uani 1 1 d .
C5 C 0.01675(14) 0.24842(12) 0.79035(12) 0.0276(2) Uani 1 1 d .
C6 C 0.10234(16) 0.09668(13) 0.78689(14) 0.0343(3) Uani 1 1 d .
H6A H 0.0234 0.0344 0.8710 0.051 Uiso 1 1 calc R
H6B H 0.2075 0.0967 0.7994 0.051 Uiso 1 1 calc R
H6C H 0.1308 0.0619 0.6881 0.051 Uiso 1 1 calc R
C7 C -0.15885(15) 0.24369(14) 0.79175(14) 0.0341(3) Uani 1 1 d .
H7A H -0.1449 0.1923 0.7066 0.051 Uiso 1 1 calc R
H7B H -0.2079 0.3410 0.7798 0.051 Uiso 1 1 calc R
H7C H -0.2359 0.1947 0.8897 0.051 Uiso 1 1 calc R
C8 C -0.01094(18) 0.30909(14) 0.93775(13) 0.0372(3) Uani 1 1 d .
H8A H -0.0804 0.2466 1.0280 0.056 Uiso 1 1 calc R
H8B H -0.0706 0.4044 0.9421 0.056 Uiso 1 1 calc R
H8C H 0.1005 0.3149 0.9371 0.056 Uiso 1 1 calc R
C9 C 0.39732(15) 0.37115(13) 0.69990(13) 0.0310(3) Uani 1 1 d .
H9A H 0.3944 0.2938 0.7794 0.046 Uiso 1 1 calc R
H9B H 0.3294 0.4556 0.7489 0.046 Uiso 1 1 calc R
H9C H 0.5163 0.3938 0.6348 0.046 Uiso 1 1 calc R
C10 C 0.59738(15) 0.22816(14) 0.39043(14) 0.0333(3) Uani 1 1 d .
H10A H 0.6562 0.2753 0.4337 0.050 Uiso 1 1 calc R
H10B H 0.6407 0.2583 0.2799 0.050 Uiso 1 1 calc R
H10C H 0.6189 0.1247 0.4064 0.050 Uiso 1 1 calc R
C11 C 0.31008(15) 0.20129(12) 0.26347(13) 0.0289(3) Uani 1 1 d .
C12 C 0.39747(19) 0.31753(15) 0.13315(14) 0.0417(3) Uani 1 1 d .
H12A H 0.3196 0.4042 0.1472 0.063 Uiso 1 1 calc R
H12B H 0.4254 0.2844 0.0337 0.063 Uiso 1 1 calc R
H12C H 0.5031 0.3381 0.1355 0.063 Uiso 1 1 calc R
C13 C 0.42478(19) 0.06110(15) 0.23799(16) 0.0407(3) Uani 1 1 d .
H13A H 0.5390 0.0784 0.2244 0.061 Uiso 1 1 calc R
H13B H 0.4349 0.0239 0.1457 0.061 Uiso 1 1 calc R
H13C H 0.3737 -0.0085 0.3276 0.061 Uiso 1 1 calc R
C14 C 0.14174(17) 0.17494(15) 0.26211(15) 0.0376(3) Uani 1 1 d .
H14A H 0.0804 0.1066 0.3498 0.056 Uiso 1 1 calc R
H14B H 0.1669 0.1365 0.1659 0.056 Uiso 1 1 calc R
H14C H 0.0703 0.2649 0.2698 0.056 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 N C1 108.08(9)
C1 O1 O2 107.08(7)
O1 C1 N 111.07(8)
O1 C1 C2 112.82(9)
N C1 C2 104.67(8)
O1 C1 C5 104.22(8)
N C1 C5 108.61(8)
C2 C1 C5 115.51(9)
C3 C2 C9 128.03(10)
C3 C2 C1 108.15(9)
C9 C2 C1 123.80(9)
C2 C3 C4 106.26(9)
C2 C3 C10 126.06(10)
C4 C3 C10 127.68(10)
N C4 C3 112.58(9)
N C4 C11 121.25(10)
C3 C4 C11 126.11(9)
C6 C5 C7 108.80(10)
C6 C5 C8 109.62(10)
C7 C5 C8 108.61(10)
C6 C5 C1 108.94(9)
C7 C5 C1 109.80(9)
C8 C5 C1 111.04(9)
C4 C11 C14 110.82(9)
C4 C11 C13 111.08(9)
C14 C11 C13 108.08(10)
C4 C11 C12 107.64(9)
C14 C11 C12 108.73(10)
C13 C11 C12 110.47(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N C4 1.2860(14)
N C1 1.4724(13)
O1 C1 1.4171(13)
O1 O2 1.4610(11)
C1 C2 1.5187(15)
C1 C5 1.5718(15)
C2 C3 1.3418(15)
C2 C9 1.4932(15)
C3 C4 1.4964(14)
C3 C10 1.4999(15)
C4 C11 1.5214(14)
C5 C6 1.5321(16)
C5 C7 1.5352(16)
C5 C8 1.5371(16)
C11 C14 1.5319(17)
C11 C13 1.5368(16)
C11 C12 1.5379(18)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H02 N 1.02(2) 1.72(2) 2.7360(12) 177.2(17) 2_566
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
O2 O1 C1 N -59.20(10)
O2 O1 C1 C2 57.96(10)
O2 O1 C1 C5 -175.97(7)
C4 N C1 O1 126.90(9)
C4 N C1 C2 4.86(11)
C4 N C1 C5 -119.05(9)
O1 C1 C2 C3 -125.89(9)
N C1 C2 C3 -5.01(11)
C5 C1 C2 C3 114.36(10)
O1 C1 C2 C9 52.73(13)
N C1 C2 C9 173.62(10)
C5 C1 C2 C9 -67.02(13)
C9 C2 C3 C4 -175.28(10)
C1 C2 C3 C4 3.26(12)
C9 C2 C3 C10 3.96(19)
C1 C2 C3 C10 -177.49(10)
C1 N C4 C3 -3.12(12)
C1 N C4 C11 179.68(9)
C2 C3 C4 N -0.16(13)
C10 C3 C4 N -179.39(11)
C2 C3 C4 C11 176.88(10)
C10 C3 C4 C11 -2.34(17)
O1 C1 C5 C6 -169.71(9)
N C1 C5 C6 71.82(11)
C2 C1 C5 C6 -45.36(12)
O1 C1 C5 C7 71.23(10)
N C1 C5 C7 -47.24(11)
C2 C1 C5 C7 -164.41(9)
O1 C1 C5 C8 -48.90(11)
N C1 C5 C8 -167.36(9)
C2 C1 C5 C8 75.46(12)
N C4 C11 C14 -14.26(15)
C3 C4 C11 C14 168.94(10)
N C4 C11 C13 -134.42(12)
C3 C4 C11 C13 48.78(15)
N C4 C11 C12 104.52(12)
C3 C4 C11 C12 -72.29(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139159974
