#------------------------------------------------------------------------------
#$Date: 2022-10-06 03:58:40 +0300 (Thu, 06 Oct 2022) $
#$Revision: 278375 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/56/7245626.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_7245626
loop_
_publ_author_name
'Grossenbacher, Philipp'
'Essers, Maria C.'
'Moser, Joël'
'Singer, Simon A.'
'Häusler, Stephanie'
'Stieger, Bruno'
'Rougier, Jean-Sébastien'
'Lochner, Martin'
_publ_section_title
;
 Bioorthogonal site-selective conjugation of fluorescent dyes to
 antibodies: method and potential applications
;
_journal_issue                   44
_journal_name_full               'RSC Advances'
_journal_page_first              28306
_journal_page_last               28317
_journal_paper_doi               10.1039/D2RA05580E
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C8 H6 Br2 N2 O2'
_chemical_formula_sum            'C8 H6 Br2 N2 O2'
_chemical_formula_weight         321.97
_chemical_name_systematic
4,5-dibromo-1-methyl-2-(prop-2-yn-1-yl)-1,2-dihydropyridazine-3,6-dione
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-09 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.57760(10)
_cell_length_b                   14.7143(2)
_cell_length_c                   17.7153(3)
_cell_measurement_reflns_used    5424
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.7690
_cell_measurement_theta_min      2.2970
_cell_volume                     1975.24(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0965
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00 104.00   1.00   20.50    --   27.84  57.00-120.00  114
  2  ω    -20.00  83.00   1.00   20.50    --   27.84 -99.00-180.00  103
  3  ω    -28.00 109.00   1.00   20.50    --   27.84  38.00   0.00  137
  4  ω    -10.00  41.00   1.00   20.50    --   27.84  57.00 120.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0413370000
_diffrn_orient_matrix_UB_12      -0.0046871000
_diffrn_orient_matrix_UB_13      0.0357121000
_diffrn_orient_matrix_UB_21      0.0839860000
_diffrn_orient_matrix_UB_22      0.0028752000
_diffrn_orient_matrix_UB_23      -0.0175267000
_diffrn_orient_matrix_UB_31      -0.0009889000
_diffrn_orient_matrix_UB_32      0.0478857000
_diffrn_orient_matrix_UB_33      0.0045386000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11246
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.144
_diffrn_reflns_theta_min         2.299
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    8.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.165
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone/ hexane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0207
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0209P)²+0.8120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0457
_refine_ls_wR_factor_ref         0.0480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1949
_reflns_number_total             2255
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra05580e3.cif
_cod_data_source_block           19ML004
_cod_database_code               7245626
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         B8H6Br2N2O2
_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_max   0.579
_shelx_estimated_absorpt_t_min   0.291
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_olex2_date_sample_data_collection 2019-09-30
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.242
_oxdiff_exptl_absorpt_empirical_full_min 0.818
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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_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
Br1 Br 0.61138(3) 0.49982(2) 0.31210(2) 0.02250(7) Uani 1 1 d . . . . .
Br2 Br 0.53000(3) 0.63537(2) 0.16148(2) 0.02367(7) Uani 1 1 d . . . . .
O1 O 0.5892(2) 0.61608(10) 0.45315(9) 0.0234(3) Uani 1 1 d . . . . .
O2 O 0.3512(2) 0.80554(10) 0.21716(9) 0.0276(4) Uani 1 1 d . . . . .
N3 N 0.4497(2) 0.73958(11) 0.40563(10) 0.0193(4) Uani 1 1 d . . . . .
N4 N 0.3910(2) 0.79090(12) 0.34328(11) 0.0197(4) Uani 1 1 d . . . . .
C1 C 0.5355(3) 0.61984(14) 0.32096(13) 0.0177(4) Uani 1 1 d . . . . .
C6 C 0.4949(3) 0.67265(14) 0.26160(12) 0.0180(4) Uani 1 1 d . . . . .
C2 C 0.5275(3) 0.65625(14) 0.39860(13) 0.0180(4) Uani 1 1 d . . . . .
C5 C 0.4102(3) 0.76211(14) 0.27061(13) 0.0197(5) Uani 1 1 d . . . . .
C9 C 0.5918(3) 0.85895(15) 0.48002(13) 0.0227(5) Uani 1 1 d . . . . .
C8 C 0.4585(3) 0.78627(15) 0.47895(13) 0.0216(5) Uani 1 1 d . . . . .
H8A H 0.4862 0.7423 0.5180 0.026 Uiso 1 1 calc R . . . .
H8B H 0.3438 0.8121 0.4904 0.026 Uiso 1 1 calc R . . . .
C7 C 0.2720(3) 0.86747(14) 0.35965(14) 0.0278(5) Uani 1 1 d . . . . .
H7A H 0.2275 0.8919 0.3132 0.033 Uiso 1 1 calc GR . . . .
H7B H 0.3357 0.9138 0.3864 0.033 Uiso 1 1 calc GR . . . .
H7C H 0.1753 0.8466 0.3901 0.033 Uiso 1 1 calc GR . . . .
C10 C 0.6929(3) 0.91980(17) 0.48051(14) 0.0299(6) Uani 1 1 d . . . . .
H10 H 0.771(4) 0.9638(18) 0.4761(16) 0.040(8) Uiso 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'
Br Br -0.2901 2.4595 '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'
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
N4 N3 C8 117.12(16) . . ?
C2 N3 N4 123.05(18) . . ?
C2 N3 C8 118.70(18) . . ?
N3 N4 C7 116.67(18) . . ?
C5 N4 N3 122.67(17) . . ?
C5 N4 C7 119.30(19) . . ?
C6 C1 Br1 123.56(17) . . ?
C6 C1 C2 120.64(19) . . ?
C2 C1 Br1 115.77(15) . . ?
C1 C6 Br2 122.60(16) . . ?
C1 C6 C5 122.1(2) . . ?
C5 C6 Br2 115.19(16) . . ?
O1 C2 N3 121.7(2) . . ?
O1 C2 C1 122.92(19) . . ?
N3 C2 C1 115.35(19) . . ?
O2 C5 N4 121.9(2) . . ?
O2 C5 C6 122.7(2) . . ?
N4 C5 C6 115.25(19) . . ?
C10 C9 C8 177.2(3) . . ?
N3 C8 C9 112.45(18) . . ?
N3 C8 H8A 109.1 . . ?
N3 C8 H8B 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N4 C7 H7A 109.5 . . ?
N4 C7 H7B 109.5 . . ?
N4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C10 H10 174.2(19) . . ?
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
Br1 C1 1.864(2) . ?
Br2 C6 1.875(2) . ?
O1 C2 1.225(3) . ?
O2 C5 1.227(3) . ?
N3 N4 1.410(2) . ?
N3 C2 1.366(3) . ?
N3 C8 1.471(3) . ?
N4 C5 1.363(3) . ?
N4 C7 1.472(3) . ?
C1 C6 1.343(3) . ?
C1 C2 1.477(3) . ?
C6 C5 1.473(3) . ?
C9 C8 1.471(3) . ?
C9 C10 1.179(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C10 H10 0.88(3) . ?
