#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/13/7121377.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_7121377
loop_
_publ_author_name
'Yruegas, Sam'
'Martinez, Jesse J.'
'Martin, Caleb Daniel'
_publ_section_title
;
 Intermolecular Insertion Reactions of Azides Into 9-Borafluorenes to
 Generate 9,10-B,N-Phenanthrenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC01529E
_journal_year                    2018
_chemical_formula_moiety         'C18 H13 B Cl N'
_chemical_formula_sum            'C18 H13 B Cl N'
_chemical_formula_weight         289.55
_chemical_name_common            8Cl
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2018-01-25 deposited with the CCDC.
2018-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.691(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4311(11)
_cell_length_b                   7.5161(6)
_cell_length_c                   17.3831(16)
_cell_measurement_reflns_used    4344
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.02
_cell_measurement_theta_min      2.37
_cell_volume                     1462.5(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1188
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33647
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.100
_diffrn_reflns_theta_min         2.393
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       blocklike
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.121
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0440P)²+0.2732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.1053
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2018
_reflns_number_total             3229
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc01529e2.cif
_cod_data_source_block           8Cl
_cod_database_code               7121377
_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.
;
_shelx_estimated_absorpt_t_min   0.920
_shelx_estimated_absorpt_t_max   0.970
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cl1 Cl 1.02030(5) 0.32275(7) 0.13200(3) 0.03520(18) Uani 1 1 d . .
N1 N 1.01724(14) 0.5283(2) 0.26244(9) 0.0223(4) Uani 1 1 d . .
B1 B 0.9763(2) 0.5117(3) 0.18105(14) 0.0242(5) Uani 1 1 d . .
C13 C 0.86157(17) 0.7985(2) 0.17970(11) 0.0238(5) Uani 1 1 d . .
C11 C 0.97243(17) 0.6635(2) 0.30566(11) 0.0232(4) Uani 1 1 d . .
C14 C 0.89843(17) 0.6577(2) 0.13645(11) 0.0228(5) Uani 1 1 d . .
C12 C 0.89301(17) 0.7930(2) 0.26616(11) 0.0236(5) Uani 1 1 d . .
C1 C 1.00404(18) 0.6654(3) 0.38769(11) 0.0275(5) Uani 1 1 d . .
H1 H 1.0590 0.5797 0.4140 0.033 Uiso 1 1 calc R U
C4 C 0.84514(18) 0.9149(3) 0.31241(12) 0.0304(5) Uani 1 1 d . .
H4 H 0.7894 1.0009 0.2872 0.036 Uiso 1 1 calc R U
C3 C 0.87619(19) 0.9141(3) 0.39312(13) 0.0355(6) Uani 1 1 d . .
H3 H 0.8424 0.9988 0.4228 0.043 Uiso 1 1 calc R U
C2 C 0.95672(19) 0.7895(3) 0.43072(12) 0.0331(5) Uani 1 1 d . .
H2 H 0.9794 0.7897 0.4864 0.040 Uiso 1 1 calc R U
C6 C 0.7724(2) 0.9431(3) 0.05772(13) 0.0403(6) Uani 1 1 d . .
H6 H 0.7300 1.0411 0.0309 0.048 Uiso 1 1 calc R U
C8 C 0.86942(18) 0.6643(3) 0.05404(11) 0.0290(5) Uani 1 1 d . .
H8 H 0.8935 0.5694 0.0246 0.035 Uiso 1 1 calc R U
C7 C 0.80726(19) 0.8043(3) 0.01502(13) 0.0358(5) Uani 1 1 d . .
H7 H 0.7883 0.8062 -0.0408 0.043 Uiso 1 1 calc R U
C5 C 0.79819(19) 0.9407(3) 0.13831(13) 0.0338(5) Uani 1 1 d . .
H5 H 0.7728 1.0367 0.1665 0.041 Uiso 1 1 calc R U
C15 C 1.11097(18) 0.4153(2) 0.30558(11) 0.0245(5) Uani 1 1 d . .
C19 C 1.1748(2) 0.1529(3) 0.37908(13) 0.0416(6) Uani 1 1 d . .
H19 H 1.1570 0.0425 0.4008 0.050 Uiso 1 1 calc R U
C17 C 1.3180(2) 0.3685(3) 0.35804(12) 0.0356(6) Uani 1 1 d . .
H17 H 1.3986 0.4073 0.3655 0.043 Uiso 1 1 calc R U
C20 C 1.0831(2) 0.2556(3) 0.33658(12) 0.0345(5) Uani 1 1 d . .
H20 H 1.0025 0.2166 0.3290 0.041 Uiso 1 1 calc R U
C18 C 1.2914(2) 0.2100(3) 0.38995(13) 0.0406(6) Uani 1 1 d . .
H18 H 1.3536 0.1396 0.4196 0.049 Uiso 1 1 calc R U
C16 C 1.22767(18) 0.4715(3) 0.31520(11) 0.0273(5) Uani 1 1 d . .
H16 H 1.2460 0.5804 0.2925 0.033 Uiso 1 1 calc R U
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'
B B 0.0013 0.0007 '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
B1 N1 C11 121.00(16)
B1 N1 C15 121.97(16)
C11 N1 C15 116.96(15)
N1 B1 C14 119.38(18)
N1 B1 Cl1 119.02(16)
C14 B1 Cl1 121.58(16)
C5 C13 C14 118.44(18)
C5 C13 C12 122.53(18)
C14 C13 C12 119.01(17)
C1 C11 C12 119.82(18)
C1 C11 N1 120.03(17)
C12 C11 N1 120.12(17)
C8 C14 C13 118.88(18)
C8 C14 B1 122.52(18)
C13 C14 B1 118.43(17)
C4 C12 C11 117.35(18)
C4 C12 C13 121.59(18)
C11 C12 C13 121.06(17)
C2 C1 C11 120.88(19)
C3 C4 C12 122.1(2)
C4 C3 C2 119.67(19)
C1 C2 C3 120.1(2)
C5 C6 C7 120.8(2)
C7 C8 C14 121.6(2)
C8 C7 C6 119.3(2)
C6 C5 C13 121.0(2)
C16 C15 C20 120.97(19)
C16 C15 N1 118.61(17)
C20 C15 N1 120.42(19)
C18 C19 C20 120.4(2)
C18 C17 C16 120.1(2)
C15 C20 C19 118.8(2)
C17 C18 C19 120.2(2)
C15 C16 C17 119.56(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 B1 1.781(2)
N1 B1 1.403(3)
N1 C11 1.420(2)
N1 C15 1.451(2)
B1 C14 1.523(3)
C13 C5 1.405(3)
C13 C14 1.411(3)
C13 C12 1.473(3)
C11 C1 1.398(3)
C11 C12 1.411(3)
C14 C8 1.404(3)
C12 C4 1.401(3)
C1 C2 1.373(3)
C4 C3 1.376(3)
C3 C2 1.381(3)
C6 C5 1.372(3)
C6 C7 1.385(3)
C8 C7 1.370(3)
C15 C16 1.377(3)
C15 C20 1.379(3)
C19 C18 1.376(3)
C19 C20 1.388(3)
C17 C18 1.374(3)
C17 C16 1.382(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139188515
