#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/57/7155764.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_7155764
loop_
_publ_author_name
'Mykhailiuk, Pavel K.'
_publ_section_title
;
 Heptafluoroisopropyl diazomethane (i-C3F7CHN2): in situ generation and
 synthesis of pyrazoles
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01579H
_journal_year                    2017
_chemical_formula_sum            'C13 H5 Br F8 N2 O'
_chemical_formula_weight         437.10
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-06-23 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.362(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.2793(12)
_cell_length_b                   8.0744(4)
_cell_length_c                   12.2026(6)
_cell_measurement_temperature    100(2)
_cell_volume                     1503.75(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.1043
_diffrn_reflns_av_sigmaI/netI    0.0949
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16423
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    2.829
_exptl_absorpt_correction_T_max  0.8715
_exptl_absorpt_correction_T_min  0.4840
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.493
_refine_diff_density_min         -1.216
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4357
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0626
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0636P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1628
_reflns_number_gt                2683
_reflns_number_total             4357
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob01579h2.cif
_cod_data_source_block           t328
_cod_original_cell_volume        1503.75(15)
_cod_database_code               7155764
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Br1 Br 0.67284(3) 0.48712(5) -0.06835(3) 0.03487(16) Uani 1 1 d .
F1 F 0.93353(16) 0.4431(3) 0.6785(2) 0.0358(6) Uani 1 1 d .
F2 F 0.89725(17) 0.7381(3) 0.7658(2) 0.0470(7) Uani 1 1 d .
F3 F 0.99723(16) 0.5896(4) 0.8857(2) 0.0419(6) Uani 1 1 d .
F4 F 0.87068(18) 0.6070(4) 0.9025(2) 0.0534(8) Uani 1 1 d .
F5 F 0.97554(17) 0.2559(3) 0.8745(2) 0.0463(7) Uani 1 1 d .
F6 F 0.8443(2) 0.2724(4) 0.8762(3) 0.0550(8) Uani 1 1 d .
F7 F 0.86815(18) 0.1588(4) 0.7305(2) 0.0517(7) Uani 1 1 d .
F8 F 0.50802(18) 0.2715(3) 0.1945(2) 0.0473(7) Uani 1 1 d .
O1 O 0.52172(19) 0.4385(4) 0.3905(2) 0.0344(7) Uani 1 1 d .
N1 N 0.6500(2) 0.5037(4) 0.6050(3) 0.0250(7) Uani 1 1 d .
H1N H 0.601(3) 0.524(4) 0.607(4) 0.016(11) Uiso 1 1 d .
N2 N 0.7209(2) 0.4984(4) 0.7009(3) 0.0253(7) Uani 1 1 d .
C1 C 0.7874(3) 0.4703(5) 0.6622(3) 0.0261(8) Uani 1 1 d .
C2 C 0.7570(3) 0.4583(5) 0.5395(3) 0.0263(8) Uani 1 1 d .
H2 H 0.7908 0.4388 0.4911 0.032 Uiso 1 1 calc R
C3 C 0.6688(3) 0.4806(5) 0.5052(3) 0.0250(8) Uani 1 1 d .
C4 C 0.5959(3) 0.4655(5) 0.3922(3) 0.0263(8) Uani 1 1 d .
C5 C 0.6168(3) 0.4740(5) 0.2821(3) 0.0258(8) Uani 1 1 d .
C6 C 0.6810(3) 0.5781(5) 0.2696(3) 0.0306(9) Uani 1 1 d .
H6 H 0.7144 0.6455 0.3335 0.037 Uiso 1 1 calc R
C7 C 0.6972(3) 0.5849(5) 0.1644(3) 0.0322(9) Uani 1 1 d .
H7 H 0.7408 0.6567 0.1557 0.039 Uiso 1 1 calc R
C8 C 0.6477(3) 0.4835(5) 0.0724(3) 0.0266(9) Uani 1 1 d .
C9 C 0.5825(3) 0.3811(5) 0.0808(3) 0.0287(9) Uani 1 1 d .
H9 H 0.5485 0.3154 0.0164 0.034 Uiso 1 1 calc R
C10 C 0.5682(3) 0.3772(5) 0.1859(3) 0.0252(8) Uani 1 1 d .
C11 C 0.8791(3) 0.4484(5) 0.7432(3) 0.0308(9) Uani 1 1 d .
C12 C 0.8927(3) 0.2820(6) 0.8083(4) 0.0370(10) Uani 1 1 d .
C13 C 0.9123(3) 0.5963(6) 0.8275(4) 0.0366(10) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
N2 N1 C3 112.7(4)
N1 N2 C1 104.8(3)
N2 C1 C2 111.0(4)
N2 C1 C11 122.2(3)
C2 C1 C11 126.8(4)
C3 C2 C1 105.1(4)
C2 C3 N1 106.4(3)
C2 C3 C4 134.0(4)
N1 C3 C4 119.1(4)
O1 C4 C3 119.9(3)
O1 C4 C5 121.6(4)
C3 C4 C5 118.3(4)
C6 C5 C10 118.1(4)
C6 C5 C4 122.6(4)
C10 C5 C4 119.2(4)
C5 C6 C7 120.9(4)
C8 C7 C6 118.3(4)
C9 C8 C7 122.5(4)
C9 C8 Br1 119.4(3)
C7 C8 Br1 118.1(3)
C8 C9 C10 117.7(4)
F8 C10 C9 117.0(3)
F8 C10 C5 120.4(3)
C9 C10 C5 122.5(4)
F1 C11 C1 108.7(3)
F1 C11 C12 105.3(3)
C1 C11 C12 112.2(4)
F1 C11 C13 105.0(3)
C1 C11 C13 112.9(4)
C12 C11 C13 112.2(4)
F5 C12 F6 108.0(4)
F5 C12 F7 107.6(4)
F6 C12 F7 107.7(4)
F5 C12 C11 112.7(4)
F6 C12 C11 111.3(4)
F7 C12 C11 109.2(4)
F3 C13 F4 108.9(4)
F3 C13 F2 106.9(4)
F4 C13 F2 107.2(4)
F3 C13 C11 112.7(4)
F4 C13 C11 111.5(4)
F2 C13 C11 109.4(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C8 1.899(4)
F1 C11 1.378(5)
F2 C13 1.344(5)
F3 C13 1.317(5)
F4 C13 1.318(5)
F5 C12 1.326(5)
F6 C12 1.328(5)
F7 C12 1.336(5)
F8 C10 1.331(4)
O1 C4 1.221(5)
N1 N2 1.328(5)
N1 C3 1.368(5)
N2 C1 1.342(5)
C1 C2 1.407(5)
C1 C11 1.487(6)
C2 C3 1.361(6)
C3 C4 1.478(6)
C4 C5 1.497(5)
C5 C6 1.391(6)
C5 C10 1.403(5)
C6 C7 1.400(5)
C7 C8 1.396(6)
C8 C9 1.377(6)
C9 C10 1.381(5)
C11 C12 1.538(6)
C11 C13 1.546(6)
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
N1 H1N O1 0.82(4) 2.03(5) 2.854(5) 177(4) 3_666
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
C3 N1 N2 C1 -0.3(4)
N1 N2 C1 C2 0.2(4)
N1 N2 C1 C11 -177.4(3)
N2 C1 C2 C3 0.0(5)
C11 C1 C2 C3 177.5(4)
C1 C2 C3 N1 -0.2(4)
C1 C2 C3 C4 -172.0(4)
N2 N1 C3 C2 0.4(4)
N2 N1 C3 C4 173.6(3)
C2 C3 C4 O1 155.5(4)
N1 C3 C4 O1 -15.5(6)
C2 C3 C4 C5 -20.9(6)
N1 C3 C4 C5 168.1(3)
O1 C4 C5 C6 146.9(4)
C3 C4 C5 C6 -36.7(6)
O1 C4 C5 C10 -31.2(6)
C3 C4 C5 C10 145.1(4)
C10 C5 C6 C7 -0.5(6)
C4 C5 C6 C7 -178.7(4)
C5 C6 C7 C8 -0.5(6)
C6 C7 C8 C9 1.8(6)
C6 C7 C8 Br1 -177.7(3)
C7 C8 C9 C10 -1.8(6)
Br1 C8 C9 C10 177.7(3)
C8 C9 C10 F8 -176.7(4)
C8 C9 C10 C5 0.7(6)
C6 C5 C10 F8 177.7(4)
C4 C5 C10 F8 -4.1(6)
C6 C5 C10 C9 0.4(6)
C4 C5 C10 C9 178.7(4)
N2 C1 C11 F1 -172.3(4)
C2 C1 C11 F1 10.5(6)
N2 C1 C11 C12 71.7(5)
C2 C1 C11 C12 -105.5(5)
N2 C1 C11 C13 -56.2(5)
C2 C1 C11 C13 126.6(4)
F1 C11 C12 F5 57.4(4)
C1 C11 C12 F5 175.4(3)
C13 C11 C12 F5 -56.2(5)
F1 C11 C12 F6 179.0(3)
C1 C11 C12 F6 -63.0(5)
C13 C11 C12 F6 65.3(5)
F1 C11 C12 F7 -62.2(4)
C1 C11 C12 F7 55.8(5)
C13 C11 C12 F7 -175.9(3)
F1 C11 C13 F3 -51.4(5)
C1 C11 C13 F3 -169.7(3)
C12 C11 C13 F3 62.4(5)
F1 C11 C13 F4 -174.3(3)
C1 C11 C13 F4 67.4(5)
C12 C11 C13 F4 -60.5(5)
F1 C11 C13 F2 67.3(4)
C1 C11 C13 F2 -51.0(5)
C12 C11 C13 F2 -178.9(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139193095
