#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/37/2003779.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2003779
loop_
_publ_author_name
'Blake, A. J.'
'Harding, M.'
'Sharp, J. T.'
_publ_section_title
;
 4-Substituted 1-Methyl-1H-2,3-benzodiazepine Compounds
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1621
_journal_page_last               1627
_journal_paper_doi               10.1107/S0108270195001120
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C16 H22 N2'
_chemical_formula_sum            'C16 H22 N2'
_chemical_formula_weight         242.36
_chemical_melting_point          375.5(5)
_chemical_name_systematic
;
 1(R)-methyl-4(1'(R),2',2'-trimethylpropyl)-1H-2,3-benzodiazepine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 102.276(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7871(9)
_cell_length_b                   10.3877(7)
_cell_length_c                   12.4807(8)
_cell_measurement_reflns_used    44
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      14.0
_cell_measurement_theta_min      12.5
_cell_volume                     1493.21(18)
_computing_cell_refinement       'DIF4 (Stoe & Cie, 1990a)'
_computing_data_collection       'DIF4 (Stoe & Cie, 1990a)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1990b)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1992)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      298(2)
_diffrn_measurement_device       'Stoe Stadi-4 four circle diffractometer'
_diffrn_measurement_method
;
  ω-2θ scans with ω width (0.8 + 0.35tanθ)°
;
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1951
_diffrn_reflns_theta_max         22.51
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Pale green'
_exptl_crystal_density_diffrn    1.078
_exptl_crystal_description       Plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.110
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.035
_refine_ls_goodness_of_fit_obs   1.219
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_restrained_S_obs      1.219
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_obs          0.0435
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;calc w = 1/[s^2^(Fo^2^) + (0.0640P)^2^ + 0.0239P]
where P = (Fo^2^ + 2Fc^2^)/3
;
_refine_ls_wR_factor_all         0.1226
_refine_ls_wR_factor_obs         0.1133
_reflns_number_observed          1265
_reflns_number_total             1951
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ha1139.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '375-376K' was changed to '375.5(5)'
- the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1493.2(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2003779
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_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
C1 1 0.6171(2) 0.4349(2) 0.7211(2) 0.0628(7) Uani d . C
H1 1 0.6738(2) 0.4599(2) 0.6777(2) 0.075 Uiso calc R H
C1m 1 0.6145(3) 0.5381(3) 0.8073(2) 0.0982(9) Uani d . C
H1MA 1 0.6912(3) 0.5499(3) 0.8511(2) 0.147 Uiso calc R H
H1MB 1 0.5631(3) 0.5117(3) 0.8535(2) 0.147 Uiso calc R H
H1MC 1 0.5874(3) 0.6176(3) 0.7717(2) 0.147 Uiso calc R H
N2 1 0.6563(2) 0.3125(2) 0.77993(14) 0.0646(6) Uani d . N
N3 1 0.7028(2) 0.2281(2) 0.73198(14) 0.0587(5) Uani d . N
C4 1 0.7105(2) 0.2348(2) 0.6208(2) 0.0491(6) Uani d . C
C41 1 0.8141(2) 0.1641(2) 0.5949(2) 0.0558(6) Uani d . C
H41 1 0.8023(2) 0.1642(2) 0.5147(2) 0.067 Uiso calc R H
C42 1 0.8097(2) 0.0221(2) 0.6280(2) 0.0829(8) Uani d . C
H42A 1 0.8753(2) -0.0226(2) 0.6116(2) 0.124 Uiso calc R H
H42B 1 0.7393(2) -0.0162(2) 0.5879(2) 0.124 Uiso calc R H
H42C 1 0.8119(2) 0.0165(2) 0.7052(2) 0.124 Uiso calc R H
C43 1 0.9328(2) 0.2307(2) 0.6374(2) 0.0641(7) Uani d . C
C44 1 0.9265(2) 0.3675(3) 0.5930(3) 0.1028(10) Uani d . C
H44A 1 0.9043(2) 0.3655(3) 0.5144(3) 0.154 Uiso calc R H
H44B 1 1.0012(2) 0.4078(3) 0.6147(3) 0.154 Uiso calc R H
H44C 1 0.8701(2) 0.4155(3) 0.6217(3) 0.154 Uiso calc R H
C45 1 0.9681(2) 0.2336(3) 0.7621(2) 0.1037(10) Uani d . C
H45A 1 0.9721(2) 0.1473(3) 0.7900(2) 0.156 Uiso calc R H
H45B 1 0.9118(2) 0.2817(3) 0.7910(2) 0.156 Uiso calc R H
H45C 1 1.0428(2) 0.2739(3) 0.7839(2) 0.156 Uiso calc R H
C46 1 1.0267(2) 0.1595(3) 0.5918(3) 0.1023(10) Uani d . C
H46A 1 1.0329(2) 0.0725(3) 0.6184(3) 0.153 Uiso calc R H
H46B 1 1.0999(2) 0.2024(3) 0.6155(3) 0.153 Uiso calc R H
H46C 1 1.0059(2) 0.1591(3) 0.5132(3) 0.153 Uiso calc R H
C5 1 0.6189(2) 0.2687(2) 0.5418(2) 0.0541(6) Uani d . C
H5 1 0.6263(2) 0.2556(2) 0.4699(2) 0.065 Uiso calc R H
C5a 1 0.5105(2) 0.3233(2) 0.5560(2) 0.0558(6) Uani d . C
C6 1 0.4074(2) 0.2963(3) 0.4794(2) 0.0751(7) Uani d . C
H6 1 0.4098(2) 0.2465(3) 0.4180(2) 0.090 Uiso calc R H
C7 1 0.3035(2) 0.3428(3) 0.4948(3) 0.0929(9) Uani d . C
H7 1 0.2354(2) 0.3234(3) 0.4444(3) 0.111 Uiso calc R H
C8 1 0.2994(3) 0.4178(3) 0.5840(3) 0.0988(11) Uani d . C
H8 1 0.2281(3) 0.4484(3) 0.5939(3) 0.119 Uiso calc R H
C9 1 0.3980(3) 0.4485(3) 0.6586(2) 0.0798(8) Uani d . C
H9 1 0.3937(3) 0.4998(3) 0.7186(2) 0.096 Uiso calc R H
C9a 1 0.5049(2) 0.4031(2) 0.6449(2) 0.0577(6) Uani d . C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.0016
H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.0000
N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0061 0.0033
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N2 C1 C9a 105.3(2) y
N2 C1 C1m 107.7(2) ?
C9a C1 C1m 117.2(2) ?
N3 N2 C1 118.9(2) y
N2 N3 C4 124.2(2) y
C5 C4 N3 121.6(2) y
C5 C4 C41 121.8(2) ?
N3 C4 C41 114.1(2) ?
C4 C41 C42 109.4(2) ?
C4 C41 C43 114.8(2) ?
C42 C41 C43 114.6(2) ?
C44 C43 C45 109.6(2) ?
C44 C43 C46 107.3(2) ?
C45 C43 C46 109.0(2) ?
C44 C43 C41 108.8(2) ?
C45 C43 C41 112.9(2) ?
C46 C43 C41 109.1(2) ?
C4 C5 C5a 127.3(2) y
C9a C5a C6 118.5(2) ?
C9a C5a C5 121.6(2) y
C6 C5a C5 119.9(2) ?
C7 C6 C5a 120.3(3) ?
C6 C7 C8 120.2(3) ?
C9 C8 C7 121.0(3) ?
C8 C9 C9a 120.1(3) ?
C9 C9a C5a 119.7(2) ?
C9 C9a C1 123.5(2) ?
C5a C9a C1 116.8(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 1.491(3) y
C1 C9a 1.493(3) y
C1 C1m 1.524(3) ?
N2 N3 1.252(2) y
N3 C4 1.412(3) y
C4 C5 1.345(3) y
C4 C41 1.518(3) ?
C41 C42 1.535(3) ?
C41 C43 1.550(3) ?
C43 C44 1.522(4) ?
C43 C45 1.524(3) ?
C43 C46 1.537(3) ?
C5 C5a 1.442(3) y
C5a C9a 1.399(3) y
C5a C6 1.405(3) ?
C6 C7 1.368(4) ?
C7 C8 1.369(4) ?
C8 C9 1.363(4) ?
C9 C9a 1.390(3) ?
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_publ_flag
C9a C1 N2 N3 78.6(2) y
C1m C1 N2 N3 -155.7(2) ?
C1 N2 N3 C4 -6.9(3) y
N2 N3 C4 C5 -45.6(3) y
N2 N3 C4 C41 151.8(2) ?
C5 C4 C41 C42 -104.9(2) ?
N3 C4 C41 C42 57.6(2) ?
C5 C4 C41 C43 124.6(2) ?
N3 C4 C41 C43 -72.9(2) ?
C4 C41 C43 C44 -55.3(3) ?
C42 C41 C43 C44 176.7(2) ?
C4 C41 C43 C45 66.5(3) ?
C42 C41 C43 C45 -61.5(3) ?
C4 C41 C43 C46 -172.1(2) ?
C42 C41 C43 C46 59.9(3) ?
N3 C4 C5 C5a 11.6(4) y
C41 C4 C5 C5a 172.8(2) ?
C4 C5 C5a C9a 31.5(3) y
C4 C5 C5a C6 -148.4(2) ?
C9a C5a C6 C7 -2.9(3) ?
C5 C5a C6 C7 177.1(2) ?
C5a C6 C7 C8 1.1(4) ?
C6 C7 C8 C9 0.5(5) ?
C7 C8 C9 C9a -0.2(4) ?
C8 C9 C9a C5a -1.6(4) ?
C8 C9 C9a C1 178.4(2) ?
C6 C5a C9a C9 3.1(3) ?
C5 C5a C9a C9 -176.8(2) ?
C6 C5a C9a C1 -176.9(2) ?
C5 C5a C9a C1 3.1(3) y
N2 C1 C9a C9 110.1(2) ?
C1m C1 C9a C9 -9.5(3) ?
N2 C1 C9a C5a -69.8(2) y
C1m C1 C9a C5a 170.5(2) ?
