#------------------------------------------------------------------------------
#$Date: 2022-03-05 00:19:51 +0200 (Sat, 05 Mar 2022) $
#$Revision: 273392 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/12/7061248.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_7061248
loop_
_publ_author_name
'Athira, Mohanakumaran'
'Smile, Suresh Snoxma'
'Shanmugam, Ponnusamy'
_publ_section_title
;
 BF3·OEt2 catalyzed synthesis of functionalized
 9-fluorene-9-ylidene appended quinazolin-4-ones
;
_journal_issue                   6
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2952
_journal_page_last               2961
_journal_paper_doi               10.1039/D1NJ05379E
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C43 H33 Br N2 O,) 0.5 (C H2 Cl2)'
_chemical_formula_sum            'C43.5 H34 Br Cl N2 O'
_chemical_formula_weight         716.09
_chemical_name_common            AM3-142
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-09-30 deposited with the CCDC.	2022-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.1530(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7423(4)
_cell_length_b                   18.5947(6)
_cell_length_c                   15.4410(5)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.43
_cell_measurement_theta_min      3.38
_cell_volume                     3749.3(2)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            72176
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        65.997
_diffrn_reflns_theta_max         65.997
_diffrn_reflns_theta_min         3.765
_exptl_absorpt_coefficient_mu    2.414
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             1476
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     548
_refine_ls_number_reflns         6524
_refine_ls_number_restraints     345
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0700
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1336P)²+1.4916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2117
_refine_ls_wR_factor_ref         0.2428
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4572
_reflns_number_total             6524
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj05379e2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7061247--7061248.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C43.50 H34 Br Cl N2 O'
_cod_database_code               7061248
_shelx_shelxl_version_number     2018/3
_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   0.713
_shelx_estimated_absorpt_t_max   0.794
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2556(3) 0.62367(18) 0.4103(2) 0.0820(9) Uani 1 1 d . . . . .
C2 C 0.3508(3) 0.6344(2) 0.4002(2) 0.0870(10) Uani 1 1 d . . . . .
H2 H 0.407370 0.642601 0.451135 0.104 Uiso 1 1 calc R U . . .
C3 C 0.3623(4) 0.6331(2) 0.3141(3) 0.1009(12) Uani 1 1 d . . . . .
H3 H 0.426263 0.641566 0.307446 0.121 Uiso 1 1 calc R U . . .
C4 C 0.2788(5) 0.6192(3) 0.2377(3) 0.1172(16) Uani 1 1 d . . . . .
H4 H 0.287285 0.618326 0.180205 0.141 Uiso 1 1 calc R U . . .
C5 C 0.1834(4) 0.6067(2) 0.2467(3) 0.1113(15) Uani 1 1 d . . . . .
H5 H 0.127655 0.597196 0.195528 0.134 Uiso 1 1 calc R U . . .
C6 C 0.1716(3) 0.60834(19) 0.3318(3) 0.0929(11) Uani 1 1 d . . . . .
C7 C 0.0807(3) 0.5977(2) 0.3605(3) 0.1021(13) Uani 1 1 d . . . . .
C8 C -0.0208(5) 0.5805(3) 0.3101(5) 0.138(2) Uani 1 1 d . . . . .
H8 H -0.040468 0.574599 0.247234 0.166 Uiso 1 1 calc R U . . .
C9 C -0.0909(4) 0.5725(3) 0.3586(7) 0.160(3) Uani 1 1 d . . . . .
H9 H -0.157895 0.559367 0.327099 0.192 Uiso 1 1 calc R U . . .
C10 C -0.0640(4) 0.5836(3) 0.4512(6) 0.144(2) Uani 1 1 d . . . . .
H10 H -0.113206 0.579532 0.480888 0.173 Uiso 1 1 calc R U . . .
C11 C 0.0346(4) 0.6005(3) 0.4997(4) 0.1179(15) Uani 1 1 d . . . . .
H11 H 0.053220 0.607004 0.562470 0.141 Uiso 1 1 calc R U . . .
C12 C 0.1071(3) 0.6078(2) 0.4543(3) 0.0943(11) Uani 1 1 d . . . . .
C13 C 0.2174(3) 0.62553(18) 0.4900(2) 0.0811(9) Uani 1 1 d . . . . .
C14 C 0.2618(3) 0.6421(2) 0.5776(2) 0.0846(9) Uani 1 1 d . . . . .
H14 H 0.217275 0.642166 0.612332 0.102 Uiso 1 1 calc R U . . .
C15 C 0.4118(3) 0.52814(17) 0.6343(2) 0.0752(8) Uani 1 1 d . . . . .
C16 C 0.3728(3) 0.48482(19) 0.5603(2) 0.0880(10) Uani 1 1 d . . . . .
H16 H 0.362873 0.502955 0.502052 0.106 Uiso 1 1 calc R U . . .
C17 C 0.3479(3) 0.4139(2) 0.5714(3) 0.1035(13) Uani 1 1 d . . . . .
H17 H 0.320091 0.385402 0.520155 0.124 Uiso 1 1 calc R U . . .
C18 C 0.3633(3) 0.3846(2) 0.6567(4) 0.1043(13) Uani 1 1 d . . . . .
C19 C 0.4042(3) 0.4294(2) 0.7309(3) 0.1020(12) Uani 1 1 d . . . . .
H19 H 0.415614 0.411308 0.789417 0.122 Uiso 1 1 calc R U . . .
C20 C 0.4283(3) 0.5001(2) 0.7199(2) 0.0904(10) Uani 1 1 d . . . . .
H20 H 0.455830 0.528924 0.770878 0.109 Uiso 1 1 calc R U . . .
C21 C 0.3377(6) 0.3071(3) 0.6699(5) 0.157(2) Uani 1 1 d . . . . .
H21A H 0.377954 0.291177 0.729420 0.235 Uiso 1 1 calc R U . . .
H21B H 0.352612 0.277640 0.624502 0.235 Uiso 1 1 calc R U . . .
H21C H 0.266295 0.303173 0.664078 0.235 Uiso 1 1 calc R U . . .
C22 C 0.386(2) 0.6759(13) 0.7327(8) 0.085(3) Uani 0.61(4) 1 d D U P A 3
C23 C 0.3310(19) 0.6399(13) 0.7819(13) 0.103(4) Uani 0.61(4) 1 d D U P A 3
H23 H 0.277534 0.609902 0.750452 0.123 Uiso 0.61(4) 1 calc R U P A 3
C24 C 0.3527(18) 0.6470(11) 0.8762(13) 0.106(4) Uani 0.61(4) 1 d D U P A 3
H24 H 0.314420 0.621070 0.905630 0.128 Uiso 0.61(4) 1 calc R U P A 3
C25 C 0.4272(17) 0.6901(10) 0.9245(10) 0.100(3) Uani 0.61(4) 1 d D U P A 3
C26 C 0.4885(18) 0.7227(11) 0.8788(12) 0.100(3) Uani 0.61(4) 1 d D U P A 3
H26 H 0.544428 0.750052 0.911765 0.121 Uiso 0.61(4) 1 calc R U P A 3
C27 C 0.4681(17) 0.7154(14) 0.7850(13) 0.092(3) Uani 0.61(4) 1 d D U P A 3
H27 H 0.511055 0.737618 0.757016 0.111 Uiso 0.61(4) 1 calc R U P A 3
C28 C 0.448(2) 0.6972(11) 1.0266(10) 0.129(5) Uani 0.61(4) 1 d D U P A 3
H28A H 0.384695 0.706679 1.038880 0.193 Uiso 0.61(4) 1 calc R U P A 3
H28B H 0.494729 0.736051 1.049456 0.193 Uiso 0.61(4) 1 calc R U P A 3
H28C H 0.476996 0.653221 1.056083 0.193 Uiso 0.61(4) 1 calc R U P A 3
C22' C 0.383(4) 0.667(2) 0.7337(13) 0.089(5) Uani 0.39(4) 1 d D U P A 4
C23' C 0.313(3) 0.6300(19) 0.7664(17) 0.091(4) Uani 0.39(4) 1 d D U P A 4
H23' H 0.262076 0.601302 0.728069 0.109 Uiso 0.39(4) 1 calc R U P A 4
C24' C 0.322(2) 0.6377(16) 0.8580(17) 0.099(4) Uani 0.39(4) 1 d D U P A 4
H24' H 0.273197 0.615400 0.879649 0.119 Uiso 0.39(4) 1 calc R U P A 4
C25' C 0.398(3) 0.6766(17) 0.9182(17) 0.101(5) Uani 0.39(4) 1 d D U P A 4
C26' C 0.457(3) 0.7207(18) 0.883(2) 0.104(5) Uani 0.39(4) 1 d D U P A 4
H26' H 0.503843 0.752534 0.920526 0.125 Uiso 0.39(4) 1 calc R U P A 4
C27' C 0.447(3) 0.717(2) 0.790(2) 0.095(5) Uani 0.39(4) 1 d D U P A 4
H27' H 0.483119 0.748844 0.765968 0.114 Uiso 0.39(4) 1 calc R U P A 4
C28' C 0.403(3) 0.681(2) 1.0172(19) 0.144(8) Uani 0.39(4) 1 d D U P A 4
H28D H 0.441800 0.640435 1.049541 0.217 Uiso 0.39(4) 1 calc R U P A 4
H28E H 0.335331 0.679364 1.021687 0.217 Uiso 0.39(4) 1 calc R U P A 4
H28F H 0.436383 0.724561 1.043226 0.217 Uiso 0.39(4) 1 calc R U P A 4
C29 C 0.5446(3) 0.61538(17) 0.6421(2) 0.0781(8) Uani 1 1 d . . . . .
C30 C 0.6202(3) 0.56233(19) 0.6691(2) 0.0864(9) Uani 1 1 d . . . . .
H30 H 0.601278 0.515023 0.675035 0.104 Uiso 1 1 calc R U . . .
C31 C 0.7223(3) 0.5790(2) 0.6871(3) 0.0968(11) Uani 1 1 d . . . . .
H31 H 0.771540 0.543061 0.705522 0.116 Uiso 1 1 calc R U . . .
C32 C 0.7518(3) 0.6491(2) 0.6778(3) 0.0961(11) Uani 1 1 d . . . . .
C33 C 0.6797(3) 0.7018(2) 0.6492(3) 0.0927(10) Uani 1 1 d . . . . .
H33 H 0.699664 0.748637 0.641889 0.111 Uiso 1 1 calc R U . . .
C34 C 0.5772(3) 0.68584(18) 0.6310(2) 0.0824(9) Uani 1 1 d . . . . .
C35 C 0.5005(3) 0.74252(19) 0.5976(2) 0.0890(10) Uani 1 1 d . . . . .
C36 C 0.3272(3) 0.78349(18) 0.5581(2) 0.0841(9) Uani 1 1 d . . . . .
C37 C 0.2911(4) 0.8221(2) 0.6173(3) 0.1077(14) Uani 1 1 d . . . . .
H37 H 0.310862 0.809793 0.678746 0.129 Uiso 1 1 calc R U . . .
C38 C 0.2254(4) 0.8793(3) 0.5856(3) 0.1188(15) Uani 1 1 d . . . . .
H38 H 0.202055 0.905177 0.626679 0.143 Uiso 1 1 calc R U . . .
C39 C 0.1935(4) 0.8991(2) 0.4957(3) 0.1069(13) Uani 1 1 d . . . . .
C40 C 0.2313(4) 0.8605(2) 0.4380(3) 0.1106(14) Uani 1 1 d . . . . .
H40 H 0.211903 0.873235 0.376786 0.133 Uiso 1 1 calc R U . . .
C41 C 0.2974(4) 0.8032(2) 0.4674(3) 0.1000(12) Uani 1 1 d . . . . .
H41 H 0.321683 0.777991 0.426320 0.120 Uiso 1 1 calc R U . . .
C42 C 0.1226(5) 0.9623(3) 0.4635(4) 0.147(2) Uani 1 1 d . . . . .
H42A H 0.153571 0.996229 0.433304 0.220 Uiso 1 1 calc R U . . .
H42B H 0.110036 0.984972 0.514872 0.220 Uiso 1 1 calc R U . . .
H42C H 0.058911 0.945851 0.421837 0.220 Uiso 1 1 calc R U . . .
N1 N 0.4410(2) 0.60106(14) 0.62089(18) 0.0775(7) Uani 1 1 d . . . . .
C43 C 0.3718(3) 0.66079(17) 0.6310(2) 0.0812(9) Uani 1 1 d D . . . .
N2 N 0.4016(2) 0.72665(14) 0.58997(18) 0.0809(7) Uani 1 1 d . . . . .
O1 O 0.5247(2) 0.80206(15) 0.5740(2) 0.1119(9) Uani 1 1 d . . . . .
Br1 Br 0.89331(4) 0.67071(4) 0.70430(6) 0.1449(4) Uani 1 1 d . . . . .
C44 C 0.5372(19) 0.9152(11) 0.444(2) 0.176(10) Uani 0.25 1 d D U P B 1
H44A H 0.509639 0.903892 0.492613 0.211 Uiso 0.25 1 calc R U P B 1
H44B H 0.480739 0.920828 0.387570 0.211 Uiso 0.25 1 calc R U P B 1
Cl1 Cl 0.6045(15) 0.9871(9) 0.4660(16) 0.309(8) Uani 0.25 1 d D U P B 1
Cl2 Cl 0.6132(17) 0.8534(11) 0.4327(15) 0.324(9) Uani 0.25 1 d D U P B 1
C44' C 0.595(3) 0.934(3) 0.3993(18) 0.237(14) Uani 0.25 1 d D U P C 2
H44C H 0.638814 0.966223 0.378992 0.284 Uiso 0.25 1 calc R U P C 2
H44D H 0.565353 0.898877 0.351634 0.284 Uiso 0.25 1 calc R U P C 2
Cl1' Cl 0.508(2) 0.9767(15) 0.427(2) 0.455(16) Uani 0.25 1 d D U P C 2
Cl2' Cl 0.6608(9) 0.8926(12) 0.4981(7) 0.272(8) Uani 0.25 1 d D U P C 2
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
_geom_angle_publ_flag
C2 C1 C6 118.8(4) . . ?
C2 C1 C13 133.2(3) . . ?
C6 C1 C13 108.0(4) . . ?
C1 C2 C3 120.0(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 120.5(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 120.9(4) . . ?
C5 C6 C7 130.8(4) . . ?
C1 C6 C7 108.2(4) . . ?
C12 C7 C8 119.9(5) . . ?
C12 C7 C6 109.1(3) . . ?
C8 C7 C6 131.1(5) . . ?
C9 C8 C7 117.3(6) . . ?
C9 C8 H8 121.4 . . ?
C7 C8 H8 121.4 . . ?
C10 C9 C8 122.2(5) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C11 C10 C9 120.2(7) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.4(6) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C7 121.0(4) . . ?
C11 C12 C13 130.2(4) . . ?
C7 C12 C13 108.8(4) . . ?
C14 C13 C12 121.3(4) . . ?
C14 C13 C1 132.8(3) . . ?
C12 C13 C1 105.8(3) . . ?
C13 C14 C43 131.7(4) . . ?
C13 C14 H14 114.2 . . ?
C43 C14 H14 114.2 . . ?
C16 C15 C20 119.1(3) . . ?
C16 C15 N1 119.2(3) . . ?
C20 C15 N1 121.6(3) . . ?
C15 C16 C17 120.4(4) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 121.6(4) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 117.1(4) . . ?
C17 C18 C21 122.1(5) . . ?
C19 C18 C21 120.8(5) . . ?
C20 C19 C18 121.4(4) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C15 C20 C19 120.5(4) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 114.8(14) . . ?
C27 C22 C43 120.7(16) . . ?
C23 C22 C43 123.3(14) . . ?
C22 C23 C24 123.1(12) . . ?
C22 C23 H23 118.5 . . ?
C24 C23 H23 118.5 . . ?
C25 C24 C23 121.2(13) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C26 117.3(13) . . ?
C24 C25 C28 119.8(12) . . ?
C26 C25 C28 122.8(12) . . ?
C27 C26 C25 121.7(15) . . ?
C27 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
C22 C27 C26 121.5(17) . . ?
C22 C27 H27 119.2 . . ?
C26 C27 H27 119.2 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27' C22' C23' 118(2) . . ?
C27' C22' C43 123(2) . . ?
C23' C22' C43 118(2) . . ?
C24' C23' C22' 118(2) . . ?
C24' C23' H23' 121.1 . . ?
C22' C23' H23' 121.1 . . ?
C25' C24' C23' 123(2) . . ?
C25' C24' H24' 118.4 . . ?
C23' C24' H24' 118.4 . . ?
C24' C25' C26' 118(2) . . ?
C24' C25' C28' 120(2) . . ?
C26' C25' C28' 122(2) . . ?
C25' C26' C27' 119(3) . . ?
C25' C26' H26' 120.4 . . ?
C27' C26' H26' 120.4 . . ?
C22' C27' C26' 122(3) . . ?
C22' C27' H27' 119.1 . . ?
C26' C27' H27' 119.1 . . ?
C25' C28' H28D 109.5 . . ?
C25' C28' H28E 109.5 . . ?
H28D C28' H28E 109.5 . . ?
C25' C28' H28F 109.5 . . ?
H28D C28' H28F 109.5 . . ?
H28E C28' H28F 109.5 . . ?
N1 C29 C30 123.3(3) . . ?
N1 C29 C34 119.4(3) . . ?
C30 C29 C34 117.1(4) . . ?
C31 C30 C29 121.1(4) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C30 C31 C32 120.2(4) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C33 C32 C31 120.1(4) . . ?
C33 C32 Br1 120.6(3) . . ?
C31 C32 Br1 119.3(3) . . ?
C32 C33 C34 120.2(4) . . ?
C32 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C33 C34 C29 121.2(4) . . ?
C33 C34 C35 119.5(3) . . ?
C29 C34 C35 119.3(4) . . ?
O1 C35 N2 121.3(4) . . ?
O1 C35 C34 121.0(4) . . ?
N2 C35 C34 117.6(3) . . ?
C37 C36 C41 118.9(4) . . ?
C37 C36 N2 121.3(3) . . ?
C41 C36 N2 119.6(3) . . ?
C36 C37 C38 119.8(4) . . ?
C36 C37 H37 120.1 . . ?
C38 C37 H37 120.1 . . ?
C39 C38 C37 122.3(4) . . ?
C39 C38 H38 118.8 . . ?
C37 C38 H38 118.8 . . ?
C40 C39 C38 116.8(4) . . ?
C40 C39 C42 122.2(4) . . ?
C38 C39 C42 121.0(5) . . ?
C39 C40 C41 122.4(4) . . ?
C39 C40 H40 118.8 . . ?
C41 C40 H40 118.8 . . ?
C36 C41 C40 119.6(4) . . ?
C36 C41 H41 120.2 . . ?
C40 C41 H41 120.2 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C29 N1 C15 117.2(3) . . ?
C29 N1 C43 118.1(3) . . ?
C15 N1 C43 117.7(3) . . ?
N2 C43 N1 107.2(3) . . ?
N2 C43 C14 108.4(3) . . ?
N1 C43 C14 109.3(3) . . ?
N2 C43 C22 108.6(8) . . ?
N1 C43 C22 110.9(12) . . ?
C14 C43 C22 112.3(11) . . ?
N2 C43 C22' 114.9(14) . . ?
N1 C43 C22' 107(2) . . ?
C14 C43 C22' 109.8(17) . . ?
C35 N2 C36 116.9(3) . . ?
C35 N2 C43 122.7(3) . . ?
C36 N2 C43 119.0(3) . . ?
Cl2 C44 Cl1 105.7(15) . . ?
Cl2 C44 H44A 110.6 . . ?
Cl1 C44 H44A 110.6 . . ?
Cl2 C44 H44B 110.6 . . ?
Cl1 C44 H44B 110.6 . . ?
H44A C44 H44B 108.7 . . ?
Cl1' C44' Cl2' 102.4(15) . . ?
Cl1' C44' H44C 111.3 . . ?
Cl2' C44' H44C 111.3 . . ?
Cl1' C44' H44D 111.3 . . ?
Cl2' C44' H44D 111.3 . . ?
H44C C44' H44D 109.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.380(6) . ?
C1 C6 1.418(5) . ?
C1 C13 1.481(5) . ?
C2 C3 1.386(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.462(6) . ?
C7 C12 1.393(6) . ?
C7 C8 1.406(7) . ?
C8 C9 1.400(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.479(5) . ?
C13 C14 1.336(5) . ?
C14 C43 1.519(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(5) . ?
C15 C20 1.374(5) . ?
C15 N1 1.447(4) . ?
C16 C17 1.387(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.386(7) . ?
C18 C21 1.513(6) . ?
C19 C20 1.379(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C27 1.380(14) . ?
C22 C23 1.394(13) . ?
C22 C43 1.548(10) . ?
C23 C24 1.399(13) . ?
C23 H23 0.9300 . ?
C24 C25 1.331(13) . ?
C24 H24 0.9300 . ?
C25 C26 1.395(13) . ?
C25 C28 1.518(12) . ?
C26 C27 1.393(13) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C22' C27' 1.384(18) . ?
C22' C23' 1.401(18) . ?
C22' C43 1.549(14) . ?
C23' C24' 1.389(17) . ?
C23' H23' 0.9300 . ?
C24' C25' 1.374(16) . ?
C24' H24' 0.9300 . ?
C25' C26' 1.380(18) . ?
C25' C28' 1.510(18) . ?
C26' C27' 1.392(18) . ?
C26' H26' 0.9300 . ?
C27' H27' 0.9300 . ?
C28' H28D 0.9600 . ?
C28' H28E 0.9600 . ?
C28' H28F 0.9600 . ?
C29 N1 1.383(5) . ?
C29 C30 1.399(5) . ?
C29 C34 1.412(5) . ?
C30 C31 1.378(6) . ?
C30 H30 0.9300 . ?
C31 C32 1.386(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.366(6) . ?
C32 Br1 1.901(4) . ?
C33 C34 1.380(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.466(5) . ?
C35 O1 1.243(4) . ?
C35 N2 1.360(5) . ?
C36 C37 1.371(6) . ?
C36 C41 1.380(5) . ?
C36 N2 1.446(5) . ?
C37 C38 1.383(6) . ?
C37 H37 0.9300 . ?
C38 C39 1.369(6) . ?
C38 H38 0.9300 . ?
C39 C40 1.367(7) . ?
C39 C42 1.508(6) . ?
C40 C41 1.382(6) . ?
C40 H40 0.9300 . ?
C41 H41 0.9300 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
N1 C43 1.502(5) . ?
C43 N2 1.493(4) . ?
C44 Cl2 1.597(19) . ?
C44 Cl1 1.600(18) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C44' Cl1' 1.60(2) . ?
C44' Cl2' 1.69(2) . ?
C44' H44C 0.9700 . ?
C44' H44D 0.9700 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 2.6(5) . . . . ?
C13 C1 C2 C3 -176.3(4) . . . . ?
C1 C2 C3 C4 -1.6(6) . . . . ?
C2 C3 C4 C5 0.1(7) . . . . ?
C3 C4 C5 C6 0.2(7) . . . . ?
C4 C5 C6 C1 0.9(6) . . . . ?
C4 C5 C6 C7 179.5(4) . . . . ?
C2 C1 C6 C5 -2.3(5) . . . . ?
C13 C1 C6 C5 176.9(3) . . . . ?
C2 C1 C6 C7 178.8(3) . . . . ?
C13 C1 C6 C7 -2.0(4) . . . . ?
C5 C6 C7 C12 -177.5(4) . . . . ?
C1 C6 C7 C12 1.3(4) . . . . ?
C5 C6 C7 C8 2.3(8) . . . . ?
C1 C6 C7 C8 -178.9(4) . . . . ?
C12 C7 C8 C9 -1.5(7) . . . . ?
C6 C7 C8 C9 178.8(5) . . . . ?
C7 C8 C9 C10 2.4(9) . . . . ?
C8 C9 C10 C11 -2.3(10) . . . . ?
C9 C10 C11 C12 1.3(9) . . . . ?
C10 C11 C12 C7 -0.5(7) . . . . ?
C10 C11 C12 C13 -180.0(4) . . . . ?
C8 C7 C12 C11 0.6(6) . . . . ?
C6 C7 C12 C11 -179.6(4) . . . . ?
C8 C7 C12 C13 -179.8(4) . . . . ?
C6 C7 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C14 -4.4(6) . . . . ?
C7 C12 C13 C14 176.0(3) . . . . ?
C11 C12 C13 C1 178.3(4) . . . . ?
C7 C12 C13 C1 -1.2(4) . . . . ?
C2 C1 C13 C14 4.2(7) . . . . ?
C6 C1 C13 C14 -174.8(4) . . . . ?
C2 C1 C13 C12 -179.0(4) . . . . ?
C6 C1 C13 C12 2.0(4) . . . . ?
C12 C13 C14 C43 178.9(3) . . . . ?
C1 C13 C14 C43 -4.8(7) . . . . ?
C20 C15 C16 C17 1.5(6) . . . . ?
N1 C15 C16 C17 177.5(4) . . . . ?
C15 C16 C17 C18 -1.3(7) . . . . ?
C16 C17 C18 C19 0.5(7) . . . . ?
C16 C17 C18 C21 -179.2(5) . . . . ?
C17 C18 C19 C20 0.0(7) . . . . ?
C21 C18 C19 C20 179.8(5) . . . . ?
C16 C15 C20 C19 -1.0(6) . . . . ?
N1 C15 C20 C19 -176.9(4) . . . . ?
C18 C19 C20 C15 0.2(7) . . . . ?
C27 C22 C23 C24 4(4) . . . . ?
C43 C22 C23 C24 172(2) . . . . ?
C22 C23 C24 C25 1(3) . . . . ?
C23 C24 C25 C26 -6(2) . . . . ?
C23 C24 C25 C28 179.2(18) . . . . ?
C24 C25 C26 C27 5(2) . . . . ?
C28 C25 C26 C27 179.9(18) . . . . ?
C23 C22 C27 C26 -5(4) . . . . ?
C43 C22 C27 C26 -172.7(18) . . . . ?
C25 C26 C27 C22 0(3) . . . . ?
C27' C22' C23' C24' -10(6) . . . . ?
C43 C22' C23' C24' -178(3) . . . . ?
C22' C23' C24' C25' -3(4) . . . . ?
C23' C24' C25' C26' 12(4) . . . . ?
C23' C24' C25' C28' -178(3) . . . . ?
C24' C25' C26' C27' -9(4) . . . . ?
C28' C25' C26' C27' -177(3) . . . . ?
C23' C22' C27' C26' 14(6) . . . . ?
C43 C22' C27' C26' -179(3) . . . . ?
C25' C26' C27' C22' -4(5) . . . . ?
N1 C29 C30 C31 178.1(3) . . . . ?
C34 C29 C30 C31 2.3(5) . . . . ?
C29 C30 C31 C32 -0.6(6) . . . . ?
C30 C31 C32 C33 -1.2(6) . . . . ?
C30 C31 C32 Br1 179.3(3) . . . . ?
C31 C32 C33 C34 1.2(6) . . . . ?
Br1 C32 C33 C34 -179.3(3) . . . . ?
C32 C33 C34 C29 0.5(6) . . . . ?
C32 C33 C34 C35 -178.1(4) . . . . ?
N1 C29 C34 C33 -178.3(3) . . . . ?
C30 C29 C34 C33 -2.2(5) . . . . ?
N1 C29 C34 C35 0.3(5) . . . . ?
C30 C29 C34 C35 176.4(3) . . . . ?
C33 C34 C35 O1 9.5(6) . . . . ?
C29 C34 C35 O1 -169.1(4) . . . . ?
C33 C34 C35 N2 -173.0(3) . . . . ?
C29 C34 C35 N2 8.4(5) . . . . ?
C41 C36 C37 C38 0.5(7) . . . . ?
N2 C36 C37 C38 175.6(5) . . . . ?
C36 C37 C38 C39 0.5(9) . . . . ?
C37 C38 C39 C40 -1.3(8) . . . . ?
C37 C38 C39 C42 -179.4(6) . . . . ?
C38 C39 C40 C41 1.1(8) . . . . ?
C42 C39 C40 C41 179.1(5) . . . . ?
C37 C36 C41 C40 -0.7(7) . . . . ?
N2 C36 C41 C40 -175.9(4) . . . . ?
C39 C40 C41 C36 -0.1(8) . . . . ?
C30 C29 N1 C15 4.7(5) . . . . ?
C34 C29 N1 C15 -179.5(3) . . . . ?
C30 C29 N1 C43 154.9(3) . . . . ?
C34 C29 N1 C43 -29.3(4) . . . . ?
C16 C15 N1 C29 -104.6(4) . . . . ?
C20 C15 N1 C29 71.3(4) . . . . ?
C16 C15 N1 C43 105.0(4) . . . . ?
C20 C15 N1 C43 -79.1(4) . . . . ?
C29 N1 C43 N2 45.1(4) . . . . ?
C15 N1 C43 N2 -164.9(3) . . . . ?
C29 N1 C43 C14 162.4(3) . . . . ?
C15 N1 C43 C14 -47.5(4) . . . . ?
C29 N1 C43 C22 -73.3(10) . . . . ?
C15 N1 C43 C22 76.8(10) . . . . ?
C29 N1 C43 C22' -78.8(14) . . . . ?
C15 N1 C43 C22' 71.3(14) . . . . ?
C13 C14 C43 N2 60.2(5) . . . . ?
C13 C14 C43 N1 -56.3(5) . . . . ?
C13 C14 C43 C22 -179.8(11) . . . . ?
C13 C14 C43 C22' -173.5(19) . . . . ?
C27 C22 C43 N2 -39(3) . . . . ?
C23 C22 C43 N2 154(2) . . . . ?
C27 C22 C43 N1 79(3) . . . . ?
C23 C22 C43 N1 -88(3) . . . . ?
C27 C22 C43 C14 -159(2) . . . . ?
C23 C22 C43 C14 35(3) . . . . ?
C27' C22' C43 N2 -21(6) . . . . ?
C23' C22' C43 N2 146(3) . . . . ?
C27' C22' C43 N1 98(5) . . . . ?
C23' C22' C43 N1 -95(4) . . . . ?
C27' C22' C43 C14 -144(4) . . . . ?
C23' C22' C43 C14 24(4) . . . . ?
O1 C35 N2 C36 -3.3(5) . . . . ?
C34 C35 N2 C36 179.2(3) . . . . ?
O1 C35 N2 C43 -169.9(3) . . . . ?
C34 C35 N2 C43 12.6(5) . . . . ?
C37 C36 N2 C35 -101.6(5) . . . . ?
C41 C36 N2 C35 73.4(5) . . . . ?
C37 C36 N2 C43 65.5(5) . . . . ?
C41 C36 N2 C43 -119.5(4) . . . . ?
N1 C43 N2 C35 -37.3(4) . . . . ?
C14 C43 N2 C35 -155.2(3) . . . . ?
C22 C43 N2 C35 82.6(13) . . . . ?
C22' C43 N2 C35 82(2) . . . . ?
N1 C43 N2 C36 156.4(3) . . . . ?
C14 C43 N2 C36 38.5(4) . . . . ?
C22 C43 N2 C36 -83.8(13) . . . . ?
C22' C43 N2 C36 -85(2) . . . . ?
