#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:33:31 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272657 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/89/7708994.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_7708994
loop_
_publ_author_name
'Mears, Kristian L.'
'Bhide, Malavika A.'
'Knapp, Caroline E.'
'Carmalt, Claire J.'
_publ_section_title
;
 Investigations into the structure, reactivity, and AACVD of aluminium and
 gallium amidoenoate complexes.
;
_journal_issue                   1
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              156
_journal_page_last               167
_journal_paper_doi               10.1039/d1dt03365d
_journal_volume                  51
_journal_year                    2021
_chemical_formula_moiety         'C9 H16 Cl2 Ga N O2'
_chemical_formula_sum            'C9 H16 Cl2 Ga N O2'
_chemical_formula_weight         310.85
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-03-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-06 deposited with the CCDC.	2021-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.2836(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.08077(15)
_cell_length_b                   8.02118(10)
_cell_length_c                   18.3319(3)
_cell_measurement_reflns_used    19522
_cell_measurement_temperature    151.6(4)
_cell_measurement_theta_max      73.5080
_cell_measurement_theta_min      4.8320
_cell_volume                     1321.34(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      151.6(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4061
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -12.00   1.00    1.00    --  -43.29 -77.00  60.00  105
  2  ω   -113.00 -17.00   1.00    1.00    --  -43.29 -57.00 -60.00   96
  3  ω   -117.00 -12.00   1.00    1.00    --  -43.29 -77.00 -90.00  105
  4  ω   -117.00 -12.00   1.00    1.00    --  -43.29 -77.00   0.00  105
  5  ω    -70.00  27.00   1.00    1.00    --  -43.29  57.00  90.00   97
  6  ω   -117.00 -12.00   1.00    1.00    --  -43.29 -77.00 150.00  105
  7  ω   -117.00 -12.00   1.00    1.00    --  -43.29 -77.00-180.00  105
  8  ω   -122.00  -6.00   1.00    1.00    --  -43.29 -19.00  60.00  116
  9  ω      1.00  83.00   1.00    1.00    --   43.29 -99.00-150.00   82
 10  ω      1.00  83.00   1.00    1.00    --   43.29 -99.00 -60.00   82
 11  ω     74.00 178.00   1.00    1.96    --  105.82  77.00 -60.00  104
 12  ω     74.00 178.00   1.00    1.96    --  105.82  77.00 120.00  104
 13  ω     78.00 176.00   1.00    1.96    --  105.82  61.00  30.00   98
 14  ω     74.00 178.00   1.00    1.96    --  105.82  77.00-120.00  104
 15  ω     94.00 177.00   1.00    1.96    --  105.82 125.00 120.00   83
 16  ω     78.00 176.00   1.00    1.96    --  105.82  61.00   0.00   98
 17  ω     77.00 177.00   1.00    1.96    --  105.82  67.00  39.34  100
 18  ω     74.00 178.00   1.00    1.96    --  105.82  77.00  90.00  104
 19  ω     25.00 109.00   1.00    1.96    --  105.82 -95.00 -90.00   84
 20  ω     74.00 178.00   1.00    1.96    --  105.82  77.00-150.00  104
 21  ω     74.00 178.00   1.00    1.96    --  105.82  77.00 -90.00  104
 22  ω     74.00 178.00   1.00    1.96    --  105.82  77.00 -30.00  104
 23  ω     78.00 176.00   1.00    1.96    --  105.82  61.00  60.00   98
 24  ω     78.00 176.00   1.00    1.96    --  105.82  61.00 -30.00   98
 25  ω     25.00 109.00   1.00    1.96    --  105.82 -95.00 150.00   84
 26  ω     78.00 176.00   1.00    1.96    --  105.82  61.00 -90.00   98
 27  ω     74.00 178.00   1.00    1.96    --  105.82  77.00   0.00  104
 28  ω     78.00 176.00   1.00    1.96    --  105.82  61.00-180.00   98
 29  ω     78.00 176.00   1.00    1.96    --  105.82  61.00 -60.00   98
 30  ω     78.00 176.00   1.00    1.96    --  105.82  61.00  90.00   98
 31  ω     78.00 176.00   1.00    1.96    --  105.82  61.00 150.00   98
 32  ω     25.00 109.00   1.00    1.96    --  105.82 -95.00  60.00   84
 33  ω     78.00 176.00   1.00    1.96    --  105.82  61.00-150.00   98
 34  ω     74.00 178.00   1.00    1.96    --  105.82  77.00-180.00  104
 35  ω     82.00 177.00   1.00    1.96    --  105.82  45.00   0.00   95
 36  ω     78.00 176.00   1.00    1.96    --  105.82  61.00-120.00   98
 37  ω     25.00 109.00   1.00    1.96    --  105.82 -95.00-150.00   84
 38  ω     78.00 176.00   1.00    1.96    --  105.82  63.00  66.60   98
 39  ω     76.00 177.00   1.00    1.96    --  105.82  69.00 154.53  101
 40  ω     74.00 178.00   1.00    1.96    --  105.82  77.00  60.00  104
 41  ω     77.00 177.00   1.00    1.96    --  105.82  66.00 117.97  100
 42  ω   -113.00 -17.00   1.00    1.00    --  -43.29 -57.00  90.00   96
 43  ω   -116.00 -21.00   1.00    1.00    --  -43.29 -38.00  60.00   95
 44  ω   -116.00 -21.00   1.00    1.00    --  -43.29 -38.00 -60.00   95
 45  ω   -113.00 -17.00   1.00    1.00    --  -43.29 -57.00-180.00   96
 46  ω   -113.00 -17.00   1.00    1.00    --  -43.29 -57.00  60.00   96
 47  ω    -43.00 130.00   1.00    1.00    --   43.29   0.00-180.00  173
 48  ω    -43.00  99.00   1.00    1.00    --   43.29   0.00 -30.00  142
 49  ω     12.00 117.00   1.00    1.00    --   43.29  77.00  60.00  105
 50  ω    -43.00 130.00   1.00    1.00    --   43.29   0.00 -60.00  173
 51  ω    -43.00 130.00   1.00    1.00    --   43.29   0.00 -90.00  173
 52  ω    -43.00 130.00   1.00    1.00    --   43.29   0.00-120.00  173
 53  ω    -43.00 130.00   1.00    1.00    --   43.29   0.00-150.00  173
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0021932000
_diffrn_orient_matrix_UB_12      -0.1910701000
_diffrn_orient_matrix_UB_13      0.0084209000
_diffrn_orient_matrix_UB_21      -0.0874040000
_diffrn_orient_matrix_UB_22      0.0180764000
_diffrn_orient_matrix_UB_23      0.0656424000
_diffrn_orient_matrix_UB_31      -0.1474069000
_diffrn_orient_matrix_UB_32      -0.0078872000
_diffrn_orient_matrix_UB_33      -0.0532363000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            44799
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.794
_diffrn_reflns_theta_min         4.876
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.439
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.563
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_preparation
'stirred solution of lithiated ligand with one equivalent of gallium chloride in toluene'
_exptl_crystal_recrystallization_method 'crystallised from toluene'
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0233
_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)+(0.0316P)²+0.5774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0597
_refine_ls_wR_factor_ref         0.0614
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2444
_reflns_number_total             2646
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt03365d2.cif
_cod_data_source_block           xstr0873
_cod_depositor_comments
'Adding full bibliography for 7708993--7708999.cif.'
_cod_original_cell_volume        1321.34(3)
_cod_database_code               7708994
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'Cl2 Ga N O2 C9 H16'
_chemical_oxdiff_usercomment     'CEK KLM'
_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.
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C7(H7)
1.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
1.c Aromatic/amide H refined with riding coordinates:
 C2(H2)
1.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C6(H6A,H6B,H6C)
;
_olex2_date_sample_data_collection 2018-06-19
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_olex2_submission_original_sample_id xstr0873
_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 1.702
_oxdiff_exptl_absorpt_empirical_full_min 0.701
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
Ga1 Ga 0.25771(2) 0.69804(2) 0.57288(2) 0.02426(8) Uani 1 1 d . . . . .
Cl1 Cl 0.04675(5) 0.79969(6) 0.59175(3) 0.04050(13) Uani 1 1 d . . . . .
Cl2 Cl 0.43484(5) 0.83322(5) 0.63961(2) 0.03072(11) Uani 1 1 d . . . . .
O1 O 0.27840(15) 0.74306(15) 0.47498(6) 0.0298(3) Uani 1 1 d . . . . .
O2 O 0.31967(16) 0.66725(15) 0.36249(7) 0.0318(3) Uani 1 1 d . . . . .
N1 N 0.27312(16) 0.46117(17) 0.57437(7) 0.0250(3) Uani 1 1 d . . . . .
C4 C 0.3128(2) 0.1925(2) 0.51533(11) 0.0317(4) Uani 1 1 d . . . . .
H4A H 0.3970 0.1605 0.5504 0.048 Uiso 1 1 calc GR . . . .
H4B H 0.3263 0.1534 0.4672 0.048 Uiso 1 1 calc GR . . . .
H4C H 0.2241 0.1442 0.5291 0.048 Uiso 1 1 calc GR . . . .
C3 C 0.29880(18) 0.3798(2) 0.51412(9) 0.0240(3) Uani 1 1 d . . . . .
C1 C 0.30352(19) 0.6245(2) 0.43093(9) 0.0246(3) Uani 1 1 d . . . . .
C7 C 0.2458(2) 0.3686(2) 0.64157(9) 0.0302(4) Uani 1 1 d . . . . .
H7 H 0.3008 0.2632 0.6434 0.036 Uiso 1 1 calc R . . . .
C2 C 0.3158(2) 0.4564(2) 0.44715(9) 0.0256(3) Uani 1 1 d . . . . .
H2 H 0.3376 0.3867 0.4096 0.031 Uiso 1 1 calc R . . . .
C8 C 0.0810(2) 0.3285(3) 0.63753(12) 0.0418(5) Uani 1 1 d . . . . .
H8A H 0.0248 0.4303 0.6344 0.063 Uiso 1 1 calc GR . . . .
H8B H 0.0647 0.2684 0.6809 0.063 Uiso 1 1 calc GR . . . .
H8C H 0.0494 0.2616 0.5947 0.063 Uiso 1 1 calc GR . . . .
C5 C 0.2953(2) 0.8400(2) 0.33994(10) 0.0331(4) Uani 1 1 d . . . . .
H5A H 0.3631 0.9128 0.3709 0.040 Uiso 1 1 calc R . . . .
H5B H 0.1940 0.8734 0.3439 0.040 Uiso 1 1 calc R . . . .
C9 C 0.3032(3) 0.4681(3) 0.71018(10) 0.0404(5) Uani 1 1 d . . . . .
H9A H 0.4061 0.4952 0.7099 0.061 Uiso 1 1 calc GR . . . .
H9B H 0.2933 0.4032 0.7532 0.061 Uiso 1 1 calc GR . . . .
H9C H 0.2465 0.5690 0.7108 0.061 Uiso 1 1 calc GR . . . .
C6 C 0.3231(3) 0.8498(3) 0.26146(11) 0.0535(6) Uani 1 1 d . . . . .
H6A H 0.2549 0.7776 0.2315 0.080 Uiso 1 1 calc GR . . . .
H6B H 0.4233 0.8157 0.2584 0.080 Uiso 1 1 calc GR . . . .
H6C H 0.3088 0.9624 0.2442 0.080 Uiso 1 1 calc GR . . . .
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga -1.2846 0.7763 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Ga1 Cl2 108.96(2) . . ?
O1 Ga1 Cl1 107.22(4) . . ?
O1 Ga1 Cl2 106.07(4) . . ?
O1 Ga1 N1 100.92(5) . . ?
N1 Ga1 Cl1 116.11(5) . . ?
N1 Ga1 Cl2 116.37(5) . . ?
C1 O1 Ga1 120.73(11) . . ?
C1 O2 C5 118.77(14) . . ?
C3 N1 Ga1 119.86(11) . . ?
C3 N1 C7 120.75(14) . . ?
C7 N1 Ga1 119.25(11) . . ?
N1 C3 C4 120.03(15) . . ?
N1 C3 C2 124.49(15) . . ?
C2 C3 C4 115.48(15) . . ?
O1 C1 O2 117.04(14) . . ?
O1 C1 C2 126.95(15) . . ?
O2 C1 C2 116.01(15) . . ?
N1 C7 C8 110.18(15) . . ?
N1 C7 C9 110.16(14) . . ?
C9 C7 C8 111.67(16) . . ?
C1 C2 C3 126.94(15) . . ?
O2 C5 C6 106.45(16) . . ?
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
Ga1 Cl1 2.1553(5) . ?
Ga1 Cl2 2.1661(5) . ?
Ga1 O1 1.8664(11) . ?
Ga1 N1 1.9050(14) . ?
O1 C1 1.289(2) . ?
O2 C1 1.329(2) . ?
O2 C5 1.454(2) . ?
N1 C3 1.332(2) . ?
N1 C7 1.490(2) . ?
C4 C3 1.508(2) . ?
C3 C2 1.401(2) . ?
C1 C2 1.382(2) . ?
C7 C8 1.522(3) . ?
C7 C9 1.518(3) . ?
C5 C6 1.498(3) . ?
